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Prospectus Supplement
(To Prospectus dated March 31, 2023)
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Filed Pursuant to Rule 424(b)(5)
Registration No. 333-270473
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11,219,516 Shares of Common Stock
Warrants to Purchase 11,219,516 Shares of Common
Stock
We are offering up to 11,219,516 shares of our
common stock and warrants to purchase up 11,219,516 shares of our common stock in this offering (and the shares of common stock issuable
from time to time upon exercise of these warrants). The common stock and warrants will be sold in units. Each warrant allows the holder
to purchase shares of common stock at an exercise price of $0.47 per share of common stock. Each unit will be sold at a negotiated price
of $0.47 per unit. The shares of common stock and warrants will be issued separately but can only be purchased together in this offering.
Units will not be issued or certificated. In connection with the offering, we also agreed to reduce the exercise price on 11,219,516 million
previously issued warrants owned by the investors participating in the offering from $2.05 to $0.47. Such previously issued warrants and
the common stock issuable upon the exercise of the previously issued warrants are not being offered pursuant to this prospectus supplement
and the accompanying prospectus.
Our common stock is listed on the Nasdaq Capital
Market under the symbol “XXII.” On June 16, 2023, the closing price of our common stock was $0.4686 per share.
We have retained Dawson James Securities, Inc.
to act as the exclusive placement agent in connection with this offering. The placement agent is not purchasing or selling any of the
common stock but has agreed to use its best efforts to arrange for the sale of the shares.
Investing in our common stock involves a high
degree of risk. You should read this prospectus supplement and the accompanying prospectus carefully before you make your investment decision.
See “Risk Factors” beginning on page S-3 of this prospectus supplement, the accompanying prospectus, and the other documents
we file or have filed with the Securities and Exchange Commission that are incorporated by reference in this prospectus supplement and
in the accompanying prospectus, for a discussion of the factors you should consider before investing in our common stock.
Neither the Securities and Exchange Commission
nor any state securities commission has approved or disapproved of these securities or determined if this prospectus is truthful or complete.
Any representation to the contrary is a criminal offense.
| | |
Per Unit | | |
Total | |
| Offering price | |
$ | 0.47 | | |
$ | 5,273,172.52 | |
| Placement Agent Fees(1) | |
$ | 0.0376 | | |
$ | 421,853.80 | |
| Proceeds, before expenses, to us | |
$ | 0.4324 | | |
$ | 4,851,318.72 | |
(1) We estimate the total expenses of this
offering, excluding the placement agent fees, will be approximately $100,000.
Delivery of the shares of common stock is expected
to be made on or about June 22, 2023.
Dawson James Securities, Inc.
The date of this prospectus supplement is June 19,
2023.
TABLE OF CONTENTS
Prospectus Supplement
Prospectus
We are offering to sell, and are seeking offers
to buy, the securities only in jurisdictions where such offers and sales are permitted. The distribution of this prospectus supplement
and the accompanying prospectus and the offering of the securities in certain jurisdictions may be restricted by law. Persons outside
the United States who come into possession of this prospectus supplement and the accompanying prospectus must inform themselves about
and observe any restrictions relating to the offering of the securities and the distribution of this prospectus supplement and the accompanying
prospectus outside the United States. This prospectus supplement and the accompanying prospectus do not constitute, and may not be used
in connection with, an offer to sell, or a solicitation of an offer to buy, any securities offered by this prospectus supplement and the
accompanying prospectus to or by any person in any jurisdiction in which it is unlawful for such person to make such an offer or solicitation.
About
This Prospectus Supplement
This prospectus supplement
relates to the offering of our securities. Before buying securities offered hereby, we urge you to read carefully this prospectus supplement,
the accompanying prospectus, and any free writing prospectus that we have authorized for use in connection with this offering, together
with the documents incorporated by reference herein, as described under the heading “Incorporation of Certain Documents by Reference.”
These documents contain important information that you should consider when making your investment decision. This prospectus supplement
contains information about the common stock offered hereby.
This document is in two parts.
The first part is this prospectus supplement, which describes the specific terms of the securities we are offering. The second part is
the accompanying prospectus, including the documents incorporated by reference therein, which provides more general information, some
of which may not apply to this offering. This prospectus supplement and the information incorporated by reference in this prospectus supplement
also may add to, update and change information contained in, or incorporated by reference into, the accompanying prospectus. Generally,
when we refer to this prospectus, we are referring to both parts of this document combined. To the extent there is a conflict between
(i) the information contained in this prospectus supplement and (ii) the information contained in the accompanying prospectus
or in any document incorporated by reference that was filed with the Securities and Exchange Commission (the “SEC”) before
the date of this prospectus supplement, you should rely on the information in this prospectus supplement. If any statement in one of these
documents is inconsistent with a statement in another document having a later date, for example, a document incorporated by reference
in this prospectus supplement or the accompanying prospectus, the statement in the document having the later date modifies or supersedes
the earlier statement.
The accompanying prospectus
is part of a registration statement that we filed with the SEC using a shelf registration process. Under the shelf registration process,
from time to time, we may offer and sell any of the securities described in the accompanying prospectus separately or together with other
securities described therein.
You should rely only on the
information contained in, or incorporated by reference into, this prospectus supplement and the accompanying prospectus and any related
free writing prospectus that we authorized to be distributed to you. Neither we nor the placement
agent have authorized anyone to provide you with different or additional information. If anyone provides you with different or
additional information, you should not rely on it. Neither we nor any of the placement agents are
making an offer to sell these shares of common stock in any jurisdiction where the offer or sale is not permitted, and you should not
consider this prospectus supplement or the accompanying prospectus to be an offer or solicitation relating to the securities in any jurisdiction
in which such an offer or solicitation relating to the securities is not authorized. You should assume that the information contained
in this prospectus supplement, the accompanying prospectus, any related free writing prospectus that we have authorized to be delivered
to you and the documents incorporated by reference herein and therein is accurate only as of their respective dates, regardless of the
time of delivery of such documents or of any sale of securities. Our business, financial condition, results of operations and prospects
may have changed since those dates. Furthermore, you should not consider this prospectus supplement or the accompanying prospectus to
be an offer or solicitation relating to the securities if the person making the offer or solicitation is not qualified to do so, or if
it is unlawful for you to receive such an offer or solicitation.
For purposes of this prospectus supplement and
the accompanying prospectus, references to “Company,” “22nd Century,” “we,” “us,” “our,”
and “ours” refer to 22nd Century Group, Inc. and its subsidiaries where the context so requires, unless otherwise indicated
or the context otherwise requires.
“Forward-Looking”
Information
This prospectus supplement and the
information incorporated by reference in this prospectus supplement include “forward-looking statements” within the
meaning of Section 27A of the Securities Act and Section 21E of the Securities Exchange Act of 1934, as amended (the
“Exchange Act”). All statements, other than statements of historical fact, included or incorporated by reference herein
regarding our expectations, beliefs, plans, objectives, prospects, financial condition, assumptions or future events are
forward-looking statements. You can identify these statements by words such as “aim,” “anticipate,”
“assume,” “believe,” “could,” “due,” “estimate,” “expect,”
“goal,” “intend,” “may,” “objective,” “plan,” “potential,”
“positioned,” “predict,” “should,” “target,” “will,” “would”
and other similar expressions that are predictions of or indicate future events and future trends. These
forward-looking statements are based on current expectations, estimates, forecasts and projections about our business and the
industry in which we operate and our management’s beliefs and assumptions. These statements are not guarantees of
future performance or development and involve known and unknown risks, uncertainties and other factors that are in some cases beyond
our control. All forward-looking statements are subject to risks and uncertainties that may cause actual results to differ
materially from those that we expected, including the following summary of risk factors:
| · | We have had a history of losses and negative
cash flows, and we may be unable to achieve and sustain profitability and positive cash flows from operations. |
| · | Our competitors generally have, and any future
competitors may have, greater financial resources and name recognition than we do, and they may therefore develop products or other technologies
similar or superior to ours, or otherwise compete more successfully than we do. |
| · | Our research and development process may not
develop marketable products, which would result in loss of our investment into such process. |
| · | We may acquire or invest in other companies,
which may divert our management’s attention, result in additional dilution to our stockholders, and consume resources that are necessary
to sustain our business or result in losses. |
| · | The failure of our information systems to function
as intended or their penetration by outside parties with the intent to corrupt them could result in business disruption, litigation and
regulatory action, and loss of revenue, assets, or personal or confidential data (cybersecurity). |
| · | We may be unsuccessful at commercializing our
Very Low Nicotine Content “VLNC” tobacco as a Modified Exposure Cigarette. |
| · | The manufacturing of tobacco products subjects
us to significant governmental regulation and the failure to comply with such regulations could have a material adverse effect on our
business and subject us to substantial fines or other regulatory actions. |
| · | We may become subject to litigation related to
cigarette smoking and/or exposure to environmental tobacco smoke, or ETS, which could severely impair our results of operations and liquidity. |
| · | The loss of a significant customer for whom we
manufacture tobacco products could have an adverse impact on our results of operation. |
| · | Product liability claims, product recalls, or
other claims could cause us to incur losses or damage our reputation. |
| · | The FDA could force the removal of our products
from the U.S. market. |
| · | Negative press from being in the hemp/cannabis
space could have a material adverse effect on our business, financial condition, and results of operations. |
| · | Any business-related cannabinoid production is
dependent on laws pertaining to the hemp/cannabis industry. |
| · | Certain of our proprietary rights have expired
or may expire or may not otherwise adequately protect our intellectual property, products and potential products, and if we cannot obtain
adequate protection of our intellectual property, products and potential products, we may not be able to successfully market our products
and potential products. |
| · | We license certain patent rights from third-party
owners. If such owners do not properly maintain or enforce the patents underlying such licenses, our competitive position and business
prospects could be harmed. |
| · | Our stock price may be highly volatile and could
decline in value. |
| · | We are a named defendant in certain litigation
matters, including federal securities class action lawsuits and derivative complaints; if we are unable to resolve these matters favorably,
then our business, operating results and financial condition may be adversely affected. |
| · | Future sales of our common stock will result
in dilution to our common stockholders. |
| · | We do not expect to declare any dividends on
our common stock in the foreseeable future. |
You also should carefully review the risk factors
and cautionary statements described in the other documents we file or furnish from time to time with the SEC, including our Annual Reports
on Form 10-K, Quarterly Reports on Form 10-Q and Current Reports on Form 8-K. The
forward-looking statements included in this prospectus supplement, the accompanying prospectus and any other offering material, or in
the documents incorporated by reference into this prospectus supplement, the accompanying prospectus and any other offering material,
are made only as of the date of the prospectus supplement, the accompanying prospectus, any other offering material or the incorporated
document.
We do not assume any obligation to update any forward-looking statements.
We disclaim any intention or obligation to update or revise any forward-looking statement, whether as a result of new information, future
events or otherwise.
Prospectus Supplement Summary
The following summary highlights basic information
about 22nd Century, this offering, and selected information contained elsewhere in or incorporated by reference into this prospectus supplement.
This summary is not complete and does not contain all of the information that you should consider before deciding whether to invest in
our common stock. You should review this entire prospectus supplement and the accompanying prospectus carefully, including our consolidated
financial statements and other information incorporated by reference in this prospectus supplement and the accompanying prospectus, before
making an investment decision. In addition, please read the “Risk Factors” section beginning on page S-3 of this prospectus
supplement.
Overview
22nd Century
Group, Inc. is a leading biotechnology company focused on utilizing advanced alkaloid plant technologies to improve health and wellness
with reduced nicotine tobacco, hemp/cannabis and hops. We use modern plant breeding technologies, including genetic engineering, gene-editing,
and molecular breeding to deliver solutions for the consumer goods and pharmaceutical industries by creating new, proprietary plants with
optimized alkaloid and flavonoid profiles as well as improved yields and valuable agronomic traits. Our mission in tobacco products is
dedicated to reduce the harms of smoking by commercializing our proprietary, very low nicotine content (“VLNC”) tobacco plants
and cigarette products. We received the first and only Food and Drug Administration (“FDA”) Modified Risk Tobacco Product
(“MRTP”) authorization of a combustible cigarette in December 2021. Beginning in April 2022, we launched our proprietary
VLN® reduced nicotine cigarettes, first through a pilot program conducted in select Circle K stores in and
around Chicago, Illinois. Following our successful pilot program, we initiated an ongoing state-by-state, region-by-region rollout
strategy.
Our mission
in hemp/cannabis is to develop and monetize proprietary varieties of hemp with valuable cannabinoid and terpene profiles and other superior
agronomic traits. We are a global scale provider of cannabinoid ingredients and Active Pharmaceutical Ingredients (“API”),
as well as a contract development and manufacturing organization (“CDMO”) provider of hemp-derived consumer
products.
In hops,
our mission is to leverage our experience with tobacco and hemp/cannabis, a close hop plant relative, to accelerate the development of
proprietary specialty hop varieties with valuable traits, for potential applications in life sciences and consumer products.
We have
a significant intellectual property portfolio of issued patents and patent applications relating to both tobacco and hemp/cannabis plants
and have further resources directed towards creating and securing additional intellectual property pertaining to all three franchises.
We continue to prioritize research and development activities to achieve our strategic and investment priorities.
Our Annual Report on Form 10-K for the year
ended December 31, 2022 and the subsequent reports filed pursuant to the Exchange Act provide additional information about our business,
operations and financial condition.
Corporate Information
We are a Nevada corporation and our corporate
headquarters is located at 500 Seneca Street, Suite 507, Buffalo, New York 14204. Our telephone number is (716) 270-1523. Our internet
address is www.xxiicentury.com. We do not incorporate the information on our website into this prospectus supplement or in the accompanying
prospectus, and you should not consider it to be a part of this prospectus supplement or the accompanying prospectus. Our web site address
is included as an inactive textual reference only.
The Offering
| Issuer |
22nd Century Group, Inc. |
| Common stock offered by us |
11,219,516 shares. |
| Common stock to be outstanding after this offering(1) |
237,910,007 shares. |
| Warrants offered by us |
Warrants to purchase 11,219,516 shares of common stock will be offered in this offering, which warrants will be exercisable immediately upon issuance and ending five years from the initial issuance date, with the exercise price being $0.47 per share of common stock. This prospectus supplement also relates to the offering of the shares of common stock issuable upon exercise of the warrants. |
| Use of proceeds |
We intend to use the net proceeds from this offering for the continued commercial expansion of its VLN® reduced nicotine content tobacco cigarettes in additional markets, working capital related to its commercial activities and general corporate purposes. See “Use of Proceeds” on page S-5 for additional information. |
| Risk factors |
An investment in our common stock involves a high degree of risk. See “Risk Factors” beginning on page S-3 of this prospectus supplement and other information included in this prospectus supplement, the accompanying prospectus and the documents incorporated by reference in this prospectus supplement and the accompanying prospectus for a discussion of factors you should carefully consider before deciding to invest in our common stock. |
| Nasdaq Capital Market symbol |
Our common stock is traded on the Nasdaq Capital Market under the symbol “XXII.” |
| (1) The number of shares outstanding after this offering is based on 226,690,491 shares of common stock outstanding as of June 16, 2023. Except as otherwise indicated, all information in this prospectus supplement assumes no exercise or settlement of outstanding options or restricted stock and no exercise of the warrants. |
RISK FACTORS
An
investment in our common stock involves a high degree of risk. Prior to making a decision about investing in our common stock, you should
consider carefully the specific risk factors discussed in the sections entitled “Risk Factors” contained in our most recent
Annual Report on Form 10-K for the year ended December 31, 2022, as filed with the SEC on March 9, 2023, which are incorporated
into this prospectus supplement and the accompanying prospectus by reference in their entirety, as updated or superseded by the risks
and uncertainties described under similar headings in the other documents that are filed after the date hereof and incorporated by reference
into this prospectus supplement and the accompanying prospectus, together with other information in this prospectus supplement and the
accompanying prospectus, the documents incorporated by reference and any free writing prospectus that we may authorize for use in connection
with this offering. These risks and uncertainties are not the only risks and uncertainties we face. Additional risks and uncertainties
not presently known to us, or that we currently view as immaterial, may also impair our business. Past financial performance may not be
a reliable indicator of future performance, and historical trends should not be unduly relied upon to anticipate results or trends in
future periods. If any of the risks or uncertainties described in our SEC filings or any additional risks and uncertainties actually occur,
our business, financial condition, results of operations and cash flow could be materially and adversely affected. In that case, the trading
price of our common stock could decline and you might lose all or part of your investment. Please also read carefully the section above
titled “Forward-Looking Information.
Risks Related to this Offering
Fluctuations in the price of our common
stock, including as a result of actual or anticipated sales of shares by us and/or our directors, officers or stockholders, may make our
common stock more difficult to resell.
The market price and trading volume of our common
stock have been, and may continue to be, subject to significant fluctuations due not only to general stock market conditions, but also
to changes in sentiment in the market regarding the industry in which we operate, our operations, business prospects or liquidity, or
this offering. In addition to the risk factors discussed in our periodic reports and in this prospectus supplement, the price and volume
volatility of our common stock may be affected by actual or anticipated sales of common stock by us and/or our directors, officers or
stockholders, whether in the market, in connection with business acquisitions, in this offering or in subsequent public offerings. Stock
markets in general have at times experienced extreme volatility unrelated to the operating performance of particular companies. These
broad market fluctuations may adversely affect the trading price of our common stock, regardless of our operating results.
As a result, these fluctuations in the market
price and trading volume of our common stock may make it difficult to predict the market price of our common stock in the future, cause
the value of your investment to decline and make it more difficult to resell our common stock.
Management will have broad discretion as
to the use of the proceeds of this offering, and we may use the proceeds in ways in which you and other stockholders may disagree.
We have not designated the amount of net proceeds
we will receive from this offering for any particular purpose. We may use a portion of the net proceeds to acquire or invest in new or
different businesses, products and intellectual property. Our management will have broad discretion over the use and investment of the
net proceeds from this offering, and, accordingly, investors in this offering will need to rely upon the judgment of our management with
respect to the use of proceeds, with only limited information concerning our specific intentions. Our stockholders may not agree
with the manner in which our management chooses to allocate and spend the net proceeds.
Investors in this offering will experience
immediate and substantial dilution in the net tangible book value per share of our common stock.
The public offering price of our common stock
will be substantially higher than the net tangible book value per share. Therefore, if you purchase shares of common stock in this offering,
you will pay a price per share that substantially exceeds our net tangible book value per share after this offering. Please refer to the
section below entitled “Dilution” for more information.
You may experience future dilution as a
result of future equity offerings or acquisitions.
In order to raise additional capital, we may in
the future offer additional shares of our common stock or other securities convertible into or exchangeable for our common stock at prices
that may not be the same as the price per share in this offering. We may sell shares or other securities in any future offering at a price
per share that is less than the price per share paid by investors in this offering, and investors purchasing shares or other securities
in the future could have rights superior to existing stockholders. The price per share at which we sell additional shares of our common
stock, or securities convertible or exchangeable into our common stock, in future transactions or acquisitions may be higher or lower
than the price per share paid by investors in this offering.
In addition, we may engage in one or more potential
acquisitions in the future, which could involve issuing our common stock as some or all of the consideration payable by us to complete
such acquisitions. If we issue common stock or securities linked to our common stock, the newly issued securities may have a dilutive
effect on the interests of the holders of our common stock. Additionally, future sales of newly issued shares used to effect an acquisition
could depress the market price of our common stock.
Our common stock may become the target of
a “short squeeze.”
In recent years, the securities of several companies
have increasingly experienced significant and extreme volatility in stock price due to short sellers of common stock and buy-and-hold
decisions of longer investors, resulting in what is sometimes described as a “short squeeze.” Short squeezes have caused extreme
volatility in those companies and in the market and have led to the price per share of those companies to trade at a significantly inflated
rate that is disconnected from the underlying value of the company. Sharp rises in a company’s stock price may force traders in
a short position to buy the shares to avoid even greater losses. Many investors who have purchased shares in those companies at an inflated
rate face the risk of losing a significant portion of their original investment as the price per share has declined steadily as interest
in those shares have abated. We may be a target of a short squeeze, and investors may lose a significant portion or all of their investment
if they purchase our shares at a rate that is significantly disconnected from our underlying value.
Use
of Proceeds
We estimate that the net proceeds
from the sale of shares in this offering will be approximately $4.8 million, after deducting placement agent and financial advisor fees
and commissions as well as our estimated expenses related to the offering.
We
intend to use the net proceeds from this offering for the continued commercial expansion
of its VLN® reduced nicotine content tobacco cigarettes in additional markets, working capital related to its commercial activities
and general corporate purposes.
Our management will have broad
discretion in the allocation of the net proceeds of this offering for any purpose, and investors will be relying on the judgment of our
management with regard to the use of these net proceeds
Dilution
Purchasers of units offered
by this prospectus supplement and the accompanying prospectus will experience an immediate dilution in the net tangible book value of
their common stock from the price paid in the offering. The net tangible book value of our common stock as of March 31, 2023 was
approximately $29.1 million, or $0.1342 per share. Net tangible book value per share of our common stock is equal to total assets minus
intangible assets, goodwill, and equity investments, less total liabilities, dividend by the total number of shares of common stock outstanding
issued and outstanding as of March 31, 2023.
Dilution per share represents
the difference between the public offering price per unit and the adjusted net tangible book value per share of our common stock after
giving effect to this offering. After reflecting the sale in this offering of 11,219,516 shares of our common stock at the public offering
price of $0.47 per share (attributing none of the offering price to the warrants), less placement agent discounts and estimated offering
expenses, the adjusted net tangible book value of our common stock as of March 31, 2023 would have been approximately $33.9 million
or $0.1484 per share. The change represents an immediate increase in net tangible book value per share of our common stock of $0.0142
per share to existing stockholders and an immediate dilution of $0.3216 per share to new investors purchasing the units in this offering.
The following table illustrates this per share dilution:
| Offering price per unit | |
$ | 0.47 | |
| Net tangible book value per share as of March 31, 2023 | |
$ | 0.1342 | |
| Increase in net tangible book value per share attributable to the offering | |
$ | 0.0142 | |
| As adjusted net tangible book value per share after giving effect to this offering | |
$ | 0.1484 | |
| Dilution per share to new investors participating in the offering | |
$ | 0.3216 | |
The table above is based on 217,057,927 shares
of common stock outstanding as of March 31, 2023, which excludes the warrants and:
| · | 17,073,175 warrants to purchase an equal number
of shares of common stock at an exercise price of $2.05 per share, of which 11,219,516 warrants are adjusted to an exercise price of $0.47
in connection with this offering. |
| · | 5,000,000 warrants to purchase an equal number
of shares of common stock at an exercise price of $1.275 per share, which warrants adjusted to 7,456,140 warrants to purchase an equal
number of shares of common stock at an exercise price of $0.855 per share as a result of this offering. |
| · | 675,000 warrants to purchase an equal number
of shares of common stock at an exercise price of $0.855 per share. |
| · | 4,705,657 shares of our common stock issuable
upon the exercise of fully vested and immediately exercisable stock options outstanding as of March 31, 2023, at a weighted-average
exercise price of $1.63 per share; |
| · | 6,569,718 shares of unvested restricted stock
units; and |
| · | 203,691 shares of our common stock reserved for
future award grants under the under the 22nd Century Group, Inc. 2021 Omnibus Incentive Plan, with an additional 3.5 million shares
reserved in connection with our Annual Meeting of Stockholders on June 16, 2023. |
To the extent outstanding options are exercised
or outstanding restricted stock units vest, there will be further dilution to investors. In addition, to the extent that we issue additional
equity securities in connection with future capital raising activities, our then-existing stockholders may experience dilution.
PLAN
OF DISTRIBUTION
Pursuant to a placement agency
agreement between us and Dawson James Securities, Inc. (“Dawson James”) we have engaged Dawson James as our exclusive
placement agent to solicit offers to purchase the shares in this offering. The placement agent is not purchasing or selling any of the
shares we are offering, and it is not required to arrange the purchase or sale of any specific number of shares or dollar amount, but
it has agreed to use commercially reasonable efforts to arrange for the sale of the shares. The placement agent may retain sub-agents
and selected dealers in connection with this offering.
The placement agent proposes
to arrange for the sale of the shares we are offering pursuant to this prospectus supplement to one or more investors through securities
purchase agreements directly between the purchasers and us. All of the shares will be sold at the same price and, we expect, at a single
closing. We established the price following negotiations with prospective investors and with reference to the prevailing market price
of our common stock, recent trends in such price and other factors. It is possible that not all of the shares we are offering pursuant
to this prospectus supplement will be sold at the closing, in which case our net proceeds would be reduced. We anticipate that the sale
of the shares will be completed on the date indicated on the cover page of this prospectus supplement, subject to customary closing
conditions. On the closing date, the following will occur:
| · | we will receive funds in the amount of the aggregate
purchase price; |
| · | Dawson James, as placement agent, will receive
the placement agent fees in accordance with the terms of the placement agency agreement; and |
| · | we will deliver the shares to the investors. |
In connection with this offering,
the placement agent may distribute this prospectus supplement and the accompanying prospectus electronically.
We will pay the placement
agent cash fees equal to eight percent (8%) of the gross proceeds from the sale of the shares in this offering. In addition, we have agreed
to pay a cash fee equal to eight percent (8%) of the gross proceeds from the sale of any securities to any purchaser in this offering
or a specified party that was introduced to us by the placement agent during the engagement of the placement agent for this offering for
a period of six (6) months following the termination of the engagement letter, which exclusive engagement terminates on December 31,
2023. In addition, we will pay the placement agent a cash fee equal to eight percent (8%) of any cash exercise of the warrants and will
reimburse their expenses, including the reimbursement of legal fees not to exceed $50,000. The following table shows the per share and
total placement agent fee we will pay to the placement agent in connection with the sale of the shares, assuming the purchase of all of
the shares we are offering.
| Per unit | |
$ | 0.0376 | |
| Total | |
$ | 421,853.80 | |
The estimated offering expenses payable by us,
excluding the placement agent fees, will be approximately $100,000.
We have agreed to indemnify the placement agent
against certain liabilities, including liabilities under the Securities Act of 1933, as amended (“Securities Act”), and liabilities
arising from breaches and representations and warranties by us as contained in the placement agency agreement. We have also agreed to
contribute to payments the placement agent may be required to make in respect of such liabilities.
Dawson James may be deemed
to be an underwriter within the meaning of Section 2(a)(11) of the Securities Act, and any commissions received by it and any profit
realized on the resale of the shares sold by it while acting as principal might be deemed to be underwriting discounts or commissions
under the Securities Act. As an underwriter, Dawson James would be required to comply with the requirements of the Securities Act and
the Exchange Act, including, without limitation, Rule 415(a)(4) under the Securities Act and Rule 10b-5 and Regulation
M under the Exchange Act. These rules and regulations may limit the timing of purchases and sales of shares by Dawson James acting
as principal. Under these rules and regulations, Dawson James:
| · | may not engage in any stabilization activity
in connection with our securities; and |
| · | may not bid for or purchase any of our securities
or attempt to induce any person to purchase any of our securities, other than as permitted under the Exchange Act, until it has completed
its participation in the distribution. |
Electronic Distribution
A prospectus supplement in
electronic format may be made available on websites or through other online services maintained by the placement agent of the offering,
or by its affiliates. Other than the prospectus supplement in electronic format, the information on the placement agent’s websites
and any information contained in any other website maintained by the placement agent is not part of this prospectus supplement or the
registration statement of which this prospectus supplement forms a part, has not been approved and/or endorsed by us or the placement
agent in its capacity as placement agent and should not be relied upon by investors.
Listing
Our common stock is listed on the Nasdaq Capital
Market under the symbol “XXII.”
Selling Restrictions
No action has been taken in
any jurisdiction (except in the United States) that would permit a public offering of our common stock, or the possession, circulation
or distribution of this prospectus supplement, the accompanying prospectus or any other material relating to us or our common stock in
any jurisdiction where action for that purpose is required. Accordingly, our common stock may not be offered or sold, directly or indirectly,
and none of this prospectus supplement, the accompanying prospectus or any other offering material or advertisements in connection with
our common stock may be distributed or published, in or from any country or jurisdiction, except in compliance with any applicable rules and
regulations of any such country or jurisdiction.
The placement agent may arrange
to sell common stock offered hereby in certain jurisdictions outside the United States, either directly or through affiliates, where they
are permitted to do so.
Affiliations
The placement agent and its
affiliates have provided, and may in the future provide, various investment banking, financial advisory and other financial services to
us and our affiliates for which they have received, and in the future may receive, advisory or transaction fees, as applicable.
Legal
Matters
The validity of the shares
of our common stock being offered hereby will be passed upon for us by Foley & Lardner LLP, Jacksonville, Florida.
Experts
The consolidated financial
statements incorporated in this Prospectus by reference to the Annual Report on Form 10-K for the year ended December 31, 2022
have been so incorporated in reliance on the report of Freed Maxick CPAs, P.C., an independent registered public accounting firm, given
on the authority of said firm as experts in auditing and accounting.
The combined consolidated
financial statements of GVB Biopharma, which appear in the Company’s Current Report on Form 8-K/A filed with the SEC on July 20,
2022, incorporated herein by reference have been so incorporated in reliance on the report of Armanino LLP, an independent registered
public accounting firm.
Where
You Can Find More Information
We file annual, quarterly
and current reports, proxy statements and other information with the SEC. The SEC maintains an Internet website at http://www.sec.gov
which contains reports, proxy and information statements and other information regarding issuers that file electronically with the SEC.
Our SEC filings are available to the public from the SEC’s Internet website.
This prospectus supplement
and the accompanying prospectus are part of a registration statement that we have filed with the SEC relating to the securities to be
offered. This prospectus supplement and the accompanying prospectus omit some of the information we have included in the registration
statement and the accompanying exhibits and schedules in accordance with the rules and regulations of the SEC, and we refer you to
the omitted information. The statements this prospectus supplement makes pertaining to the content of any contract, agreement or other
document that is an exhibit to the registration statement necessarily are summaries of their material provisions and do not describe all
provisions, exceptions and qualifications contained in those contracts, agreements or documents. You should read those contracts, agreements
or documents for information that may be important to you. The registration statement, exhibits and schedules are available through its
Internet website.
Incorporation
of Certain Documents by Reference
The SEC allows us to “incorporate
by reference” much of the information we file with the SEC, which means that we can disclose important information to you by referring
you to those publicly available documents. The information that we incorporate by reference in this prospectus supplement is considered
to be part of this prospectus supplement. Because we are incorporating by reference future filings with the SEC, this prospectus supplement
is continually updated and those future filings may modify or supersede some of the information included or incorporated in this prospectus
supplement. This means that you must look at all of the SEC filings that we incorporate by reference to determine if any of the statements
in this prospectus supplement or in any document previously incorporated by reference have been modified or superseded. This prospectus
supplement incorporates by reference the documents listed below and any future filings we make with the SEC under Sections 13(a), 13(c),
14 or 15(d) of the Exchange Act (in each case, other than information furnished under Item 2.02 or Item 7.01 of Form 8-K) on
or after the date of this prospectus supplement until the earlier of the date on which all of the securities registered hereunder have
been sold or the registration statement of which this prospectus is a part has been withdrawn:
| · | Our Current Reports on Form 8-K filed with
the SEC on May 18, 2022 (including the Form 8-K/A filed on July 20, 2022 and the Form 8-K/A filed on March 10, 2023), March 3, 2023, March 10, 2023, March 31, 2023, April 5, 2023 and April 21, 2023; |
| · | The description of our common stock contained
in or incorporated into our Registration Statement on Form 8-A, filed August 12, 2021, and any amendment or report updating
that description. |
We will provide without charge to each person
to whom a prospectus is delivered a copy of any or all of the information that has been incorporated by reference into but not delivered
with this prospectus supplement. Requests should be directed to our principal executive offices at:
22nd Century Group, Inc.
500 Seneca Street, Suite 507
Buffalo, New York 14204
(716) 270-1523
You should rely only on the
information contained in this prospectus supplement, including information incorporated by reference herein as described above, the accompanying
prospectus (including information incorporated by reference therein) and any free writing prospectus that we may authorize to be delivered
to you. We have not authorized anyone to provide you with different information. If anyone provides you with different or inconsistent
information, you should not rely on it. You should not assume that the information in this prospectus supplement or the accompanying prospectus
is accurate as of any date other than the date on the front of those documents or that any document incorporated by reference is accurate
as of any date other than its filing date. You should not consider this prospectus supplement or the accompanying prospectus to be an
offer or solicitation relating to the securities in any jurisdiction in which such an offer or solicitation relating to the securities
is not authorized. Furthermore, you should not consider this prospectus supplement or the accompanying prospectus to be an offer or solicitation
relating to the securities if the person making the offer or solicitation is not qualified to do so, or if it is unlawful for you to receive
such an offer or solicitation.
PROSPECTUS
22nd Century Group, Inc.
DEBT SECURITIES
COMMON STOCK
PREFERRED STOCK
WARRANTS
SUBSCRIPTION RIGHTS
SECURITIES PURCHASE CONTRACTS
UNITS
We may offer and sell from
time to time up to $250 million of any combination of the securities described in this prospectus, from time to time, in one or more offerings,
in amounts, at prices and on terms determined at the times of offerings.
This prospectus describes
the general manner in which our securities may be offered using this prospectus. We will provide specific terms of the securities, including
the offering prices, in one or more supplements to this prospectus. The supplements may also add, update or change information contained
in this prospectus. You should read this prospectus and the prospectus supplement relating to the specific issue of securities carefully
before you invest.
We may offer the securities
for sale directly to the purchasers or through one or more underwriters, dealers and agents to be designated at a future date. The supplements
to this prospectus will provide the specific terms of the plan of distribution.
Our common stock is listed on the Nasdaq Capital
Market under the symbol “XXII.” The last reported sale price of the common stock on March 6, 2023 was $0.9356 per share.
Each prospectus supplement will indicate if the securities offered thereby will be listed on any securities exchange.
Investing in our securities
involves risk. Please read carefully the section entitled “Risk Factors” on Page 1 of this prospectus and any similar
section contained in the applicable prospectus supplement and/or other offering material concerning factors you should consider before
investing in our securities which may be offered hereby.
Neither the Securities
and Exchange Commission nor any state securities commission has approved or disapproved of these securities or determined if this prospectus
is truthful or complete. Any representation to the contrary is a criminal offense.
The date of this prospectus is March 31, 2023.
TABLE OF CONTENTS
ABOUT
THIS PROSPECTUS
Unless the context otherwise
requires, references in this prospectus to “Company,” “22nd Century,” “we,” “us,” “our,”
and “ours” refer to 22nd Century Group, Inc. and its subsidiaries where the context so requires.
This prospectus is part of
a registration statement on Form S-3 that we filed with the Securities and Exchange Commission, or the SEC, using a “shelf”
registration process. Under this shelf registration process, we may, from time to time, sell the securities described in this prospectus,
in one or more offerings, up to the maximum aggregate dollar amount $250 million. This prospectus provides you with a general description
of the securities that we may offer. Each time we offer securities, we will provide a prospectus supplement and/or other offering
material that will contain specific information about the terms of that offering. The prospectus supplement and/or other offering material
may also add, update or change information contained in this prospectus. You should read this prospectus and the applicable prospectus
supplement and any other offering material together with the additional information described under the heading “Where You Can Find
More Information.”
You should rely only on the
information contained or incorporated by reference in this prospectus and in any prospectus supplement or other offering material. We
have not authorized any other person to provide you with different information. If anyone provides you with different or inconsistent
information, you should not rely on it. We are not making offers to sell the securities in any jurisdiction in which an offer is not authorized
or in which the person making that offer is not qualified to do so or to anyone to whom it is unlawful to make an offer. You should not
assume that the information contained in this prospectus or any prospectus supplement or any other offering material, or the information
we previously filed with the SEC that we incorporate by reference in this prospectus or any prospectus supplement, is accurate as of any
date other than its respective date. Our business, financial condition, results of operations and prospects may have changed since
those dates.
RISK
FACTORS
Investing in our securities
involves risks. Before making an investment decision, you should carefully consider the risks and other information we include or incorporate
by reference in this prospectus and any prospectus supplement. In particular, you should consider the risk factors described under the
heading “Risk Factors” in our most recent Annual Report on Form 10-K as may be revised or supplemented by our subsequent
Quarterly Reports on Form 10-Q or Current Reports of Form 8-K, each of which are on file with the SEC and are incorporated herein
by reference, and which may be amended, supplemented or superseded from time to time by other reports we file with the SEC in the future.
In addition to those risk factors, there may be additional risks and uncertainties which are not currently known to us or that we currently
deem immaterial. Our business, financial condition or results of operations could be materially adversely affected by any of these
risks. The occurrence of any of these risks might cause you to lose all or part of your investment in the offered securities. Additional
risk factors may be included in a prospectus supplement relating to a particular offering of securities.
“FORWARD-LOOKING”
INFORMATION
This registration statement
and the information incorporated by reference herein include “forward-looking statements” within the meaning of Section 27A
of the Securities Act and Section 21E of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). All statements,
other than statements of historical fact, included or incorporated by reference herein regarding our expectations, beliefs, plans, objectives,
prospects, financial condition, assumptions or future events are forward-looking statements. You can identify these statements by words
such as “aim,” “anticipate,” “assume,” “believe,” “could,” “due,”
“estimate,” “expect,” “goal,” “intend,” “may,” “objective,” “plan,”
“potential,” “positioned,” “predict,” “should,” “target,” “will,”
“would” and other similar expressions that are predictions of or indicate future events and future trends. These forward-looking
statements are based on current expectations, estimates, forecasts and projections about our business and the industry in which we operate
and our management’s beliefs and assumptions. These statements are not guarantees of future performance or development and involve
known and unknown risks, uncertainties and other factors that are in some cases beyond our control. All forward-looking statements are
subject to risks and uncertainties that may cause actual results to differ materially from those that we expected, including the following
summary of risk factors:
| · | We have had a history of losses and negative cash flows, and we may be unable to achieve and sustain profitability
and positive cash flows from operations. |
| · | Our competitors generally have, and any future competitors may have, greater financial resources and name
recognition than we do, and they may therefore develop products or other technologies similar or superior to ours, or otherwise compete
more successfully than we do. |
| · | Our research and development process may not develop marketable products, which would result in loss of
our investment into such process. |
| · | Our ability to successfully integrate the operations of GVB Biopharma into ours and achieve the expected
synergies with the acquired business. |
| · | We may acquire or invest in other companies, which may divert our management’s attention, result
in additional dilution to our stockholders, and consume resources that are necessary to sustain our business or result in losses. |
| · | The coronavirus pandemic (COVID-19) or another pandemic may cause a variety of business disruptions and
future business risks. |
| · | The failure of our information systems to function as intended or their penetration by outside parties
with the intent to corrupt them could result in business disruption, litigation and regulatory action, and loss of revenue, assets, or
personal or confidential data (cybersecurity). |
| · | We may be unsuccessful at commercializing our Very Low Nicotine Content “VLNC” tobacco as
a Modified Exposure Cigarette. |
| · | The manufacturing of tobacco products subjects us to significant governmental regulation and the failure
to comply with such regulations could have a material adverse effect on our business and subject us to substantial fines or other regulatory
actions. |
| · | We may become subject to litigation related to cigarette smoking and/or exposure to environmental tobacco
smoke, or ETS, which could severely impair our results of operations and liquidity. |
| · | The loss of a significant customer for whom we manufacture tobacco products could have an adverse impact
on our results of operation. |
| · | Product liability claims, product recalls, or other claims could cause us to incur losses or damage our
reputation. |
| · | The FDA could force the removal of our products from the U.S. market. |
| · | Negative press from being in the hemp/cannabis space could have a material adverse effect on our business,
financial condition, and results of operations. |
| · | Any business-related cannabinoid production is dependent on laws pertaining to the hemp/cannabis industry. |
| · | Certain of our proprietary rights have expired or may expire or may not otherwise adequately protect our
intellectual property, products and potential products, and if we cannot obtain adequate protection of our intellectual property, products
and potential products, we may not be able to successfully market our products and potential products. |
| · | We license certain patent rights from third-party owners. If such owners do not properly maintain or enforce
the patents underlying such licenses, our competitive position and business prospects could be harmed. |
| · | Our stock price may be highly volatile and could decline in value. |
| · | We are a named defendant in certain litigation matters, including federal securities class action lawsuits
and derivative complaints; if we are unable to resolve these matters favorably, then our business, operating results and financial condition
may be adversely affected. |
| · | Future sales of our common stock will result in dilution to our common stockholders. |
| · | We do not expect to declare any dividends on our common stock in the foreseeable future. |
You also should carefully
review the risk factors and cautionary statements described in the other documents we file or furnish from time to time with the SEC,
including our Annual Reports on Form 10-K, Quarterly Reports on Form 10-Q and Current Reports on Form 8-K. The forward-looking
statements included in this prospectus and any other offering material, or in the documents incorporated by reference into this prospectus
and any other offering material, are made only as of the date of the prospectus and any other offering material or the incorporated document.
We do not assume any obligation
to update any forward-looking statements. We disclaim any intention or obligation to update or revise any forward-looking statement, whether
as a result of new information, future events or otherwise.
22ND
CENTURY GROUP, INC.
22nd
Century Group, Inc. is a leading biotechnology company focused on utilizing advanced alkaloid plant technologies to improve health
and wellness with reduced nicotine tobacco, hemp/cannabis and hops. We use modern plant breeding technologies, including genetic engineering,
gene-editing, and molecular breeding to deliver solutions for the consumer goods and pharmaceutical industries by creating new, proprietary
plants with optimized alkaloid and flavonoid profiles as well as improved yields and valuable agronomic traits. Our mission in tobacco
products is dedicated to reduce the harms of smoking by commercializing our proprietary, very low nicotine content (“VLNC”)
tobacco plants and cigarette products. We received the first and only Food and Drug Administration (“FDA”) Modified Risk Tobacco
Product (“MRTP”) authorization of a combustible cigarette in December 2021. Beginning in April 2022, we launched
our proprietary VLN® reduced
nicotine cigarettes, first through a pilot program conducted in select Circle K stores in and around Chicago, Illinois. Following
our successful pilot program, we initiated an ongoing state-by-state, region-by-region rollout strategy.
Our
mission in hemp/cannabis is to develop and monetize proprietary varieties of hemp with valuable cannabinoid and terpene profiles and other
superior agronomic traits. We are a global scale provider of cannabinoid ingredients and Active Pharmaceutical Ingredients (“API”),
as well as a contract development and manufacturing organization (“CDMO”) provider of hemp-derived consumer
products.
In hops,
our mission is to leverage our experience with tobacco and hemp/cannabis, a close hop plant relative, to accelerate the development of
proprietary specialty hop varieties with valuable traits, for potential applications in life sciences and consumer products.
We
have a significant intellectual property portfolio of issued patents and patent applications relating to both tobacco and hemp/cannabis
plants and have further resources directed towards creating and securing additional intellectual property pertaining to all three franchises.
We continue to prioritize research and development activities to achieve our strategic and investment priorities.
Our Annual Report on Form 10-K
for the year ended December 31, 2022 and the subsequent reports filed pursuant to the Exchange Act provide additional information
about our business, operations and financial condition.
We are a Nevada corporation
and our corporate headquarters is located at 500 Seneca Street, Suite 507, Buffalo, New York 14204. Our telephone number is (716)
270-1523. Our internet address is www.xxiicentury.com. We do not incorporate the information on our website into this prospectus, and
you should not consider it to be a part of this prospectus. Our web site address is included as an inactive textual reference only.
USE
OF PROCEEDS
We intend to use the net proceeds from the sale
of the securities as set forth in the applicable prospectus supplement. Pending such use, we may temporarily invest the net proceeds in
short-term investments.
DILUTION
We will set forth in a prospectus supplement the
following information regarding any material dilution of the equity interests of investors purchasing securities in an offering under
this prospectus:
| · | the net tangible book value per share of our equity securities before and after the offering; |
| · | the amount of the increase in such net tangible book value per share attributable to the cash payments made by purchasers in the offering;
and |
| · | the amount of the immediate dilution from the public offering price which will be absorbed by such purchasers. |
SECURITIES
TO BE OFFERED
We may offer, from time to
time and in one or more offerings, debt securities, shares of common stock, shares of preferred stock, warrants, subscription rights,
securities purchase contracts and units. Set forth herein and below is a general description of the securities that we may offer hereunder.
We will set forth in the applicable prospectus supplement a specific description of the securities that may be offered under this prospectus.
The terms of the offering of securities, the initial offering price and the net proceeds will be contained in the prospectus supplement
and/or other offering material relating to such offering.
DESCRIPTION
OF DEBT SECURITIES
The following description,
together with the additional information we include in any applicable prospectus supplement, summarizes certain general terms and provisions
of the debt securities that we may offer under this prospectus. When we offer to sell a particular series of debt securities, we will
describe the specific terms of the series in a supplement to this prospectus. We will also indicate in the supplement to what extent the
general terms and provisions described in this prospectus apply to a particular series of debt securities.
We may issue debt securities
either separately, or together with, or upon the conversion or exercise of or in exchange for, other securities described in this prospectus.
Debt securities may be our senior, senior subordinated or subordinated obligations and, unless otherwise specified in a supplement to
this prospectus, the debt securities will be our direct, unsecured obligations and may be issued in one or more series.
The debt securities will
be issued under an indenture between us and a trustee to be identified in an accompanying prospectus supplement. We have summarized select
portions of the indenture below. The summary is not complete. The form of the indenture has been filed as an exhibit to the registration
statement of which this prospectus forms a part and you should read the indenture for provisions that may be important to you. In the
summary below, we have included references to the section numbers of the indenture so that you can easily locate these provisions. Capitalized
terms used in the summary and not defined herein have the meanings specified in the indenture.
General
The terms of each series
of debt securities will be established by or pursuant to a resolution of our board of directors and set forth or determined in the manner
provided in a resolution of our board of directors, in an officer’s certificate or by a supplemental indenture. The particular terms
of each series of debt securities will be described in a prospectus supplement relating to such series (including any pricing supplement
or term sheet).
We can issue an unlimited
amount of debt securities under the indenture that may be in one or more series with the same or various maturities, at par, at a premium,
or at a discount. We will set forth in a prospectus supplement (including any pricing supplement or term sheet) relating to any series
of debt securities being offered the aggregate principal amount and the following terms of the debt securities, if applicable:
| · | the title and ranking of the debt securities (including the terms of any subordination provisions); |
| · | the price or prices (expressed as a percentage of the principal amount) at which we will sell the debt
securities; |
| · | any limit upon the aggregate principal amount of the debt securities; |
| · | the date or dates on which the principal of the securities of the series is payable; |
| · | the rate or rates (which may be fixed or variable) per annum or the method used to determine the rate
or rates (including any commodity, commodity index, stock exchange index or financial index) at which the debt securities will bear interest,
the date or dates from which interest will accrue, the date or dates on which interest will commence and be payable and any regular record
date for the interest payable on any interest payment date; |
| · | the place or places where principal of, and interest, if any, on the debt securities will be payable (and
the method of such payment), where the securities of such series may be surrendered for registration of transfer or exchange, and where
notices and demands to us in respect of the debt securities may be delivered; |
| · | the period or periods within which, the price or prices at which and the terms and conditions upon which
we may redeem the debt securities; |
| · | any obligation we have to redeem or purchase the debt securities pursuant to any sinking fund or analogous
provisions or at the option of a holder of debt securities and the period or periods within which, the price or prices at which and the
terms and conditions upon which securities of the series shall be redeemed or purchased, in whole or in part, pursuant to such obligation; |
| · | the dates on which and the price or prices at which we will repurchase debt securities at the option of
the holders of debt securities and other detailed terms and provisions of these repurchase obligations; |
| · | the denominations in which the debt securities will be issued, if other than denominations of $1,000 and
any integral multiple thereof; |
| · | whether the debt securities will be issued in the form of certificated debt securities or global debt
securities; |
| · | the portion of principal amount of the debt securities payable upon declaration of acceleration of the
maturity date, if other than the principal amount; |
| · | the currency of denomination of the debt securities, which may be United States dollars or any foreign
currency, and if such currency of denomination is a composite currency, the agency or organization, if any, responsible for overseeing
such composite currency; |
| · | the designation of the currency, currencies or currency units in which payment of principal of, premium
and interest on the debt securities will be made; |
| · | if payments of principal of, premium or interest on the debt securities will be made in one or more currencies
or currency units other than that or those in which the debt securities are denominated, the manner in which the exchange rate with respect
to these payments will be determined; |
| · | the manner in which the amounts of payment of principal of, premium, if any, or interest on the debt securities
will be determined, if these amounts may be determined by reference to an index based on a currency or currencies or by reference to a
commodity, commodity index, stock exchange index or financial index; |
| · | any provisions relating to any security provided for the debt securities; |
| · | any addition to, deletion of or change in the Events of Default described in this prospectus or in the
indenture with respect to the debt securities and any change in the acceleration provisions described in this prospectus or in the indenture
with respect to the debt securities; |
| · | any addition to, deletion of or change in the covenants described in this prospectus or in the indenture
with respect to the debt securities; |
| · | any depositaries, interest rate calculation agents, exchange rate calculation agents or other agents with
respect to the debt securities; |
| · | any other terms of the debt securities, which may supplement, modify or delete any provision of the indenture
as it applies to that series, including any terms that may be required under applicable law or regulations or advisable in connection
with the marketing of the securities; and |
| · | whether any of our direct or indirect subsidiaries will guarantee the debt securities of that series,
including the terms of subordination, if any, of such guarantees. |
We may issue debt securities
that provide for an amount less than their stated principal amount to be due and payable upon declaration of acceleration of their maturity
pursuant to the terms of the indenture. We will provide you with information on the federal income tax considerations and other special
considerations applicable to any of these debt securities in the applicable prospectus supplement.
If we denominate the purchase
price of any of the debt securities in a foreign currency or currencies or a foreign currency unit or units, or if the principal of and
any premium and interest on any series of debt securities is payable in a foreign currency or currencies or a foreign currency unit or
units, we will provide you with information on the restrictions, elections, general tax considerations, specific terms and other information
with respect to that issue of debt securities and such foreign currency or currencies or foreign currency unit or units in the applicable
prospectus supplement.
Transfer and Exchange
Each debt security will be
represented by either one or more global securities registered in the name of a clearing agency registered under the Exchange Act, which
we refer to as the depositary, or a nominee of the depositary (we will refer to any debt security represented by a global debt security
as a “book-entry debt security”), or a certificate issued in definitive registered form (we will refer to any debt security
represented by a certificated security as a “certificated debt security”) as set forth in the applicable prospectus supplement.
Except as set forth under the heading “Global Debt Securities and Book-Entry System” below, book-entry debt securities will
not be issuable in certificated form.
Certificated Debt Securities
You may transfer or exchange
certificated debt securities at any office we maintain for this purpose in accordance with the terms of the indenture. No service charge
will be made for any transfer or exchange of certificated debt securities, but we may require payment of a sum sufficient to cover any
tax or other governmental charge payable in connection with a transfer or exchange.
You may effect the transfer
of certificated debt securities and the right to receive the principal of, premium and interest on certificated debt securities only by
surrendering the certificate representing those certificated debt securities and either reissuance by us or the trustee of the certificate
to the new holder or the issuance by us or the trustee of a new certificate to the new holder.
Global Debt Securities
and Book-Entry System
Each global debt security
representing book-entry debt securities will be deposited with, or on behalf of, the depositary, and registered in the name of the depositary
or a nominee of the depositary.
Covenants
We will set forth in the
applicable prospectus supplement any restrictive covenants applicable to any issue of debt securities.
No Protection in the
Event of a Change of Control
Unless we state otherwise
in the applicable prospectus supplement, the debt securities will not contain any provisions which may afford holders of the debt securities
protection in the event we have a change in control or in the event of a highly leveraged transaction (whether or not such transaction
results in a change in control) which could adversely affect holders of debt securities.
Conversion or Exchange Rights
For any series of debt securities
that are convertible into or exchangeable for shares of our common stock, we will set forth in the applicable prospectus supplement the
terms on which such series of debt securities may be convertible into or exchangeable for our common stock. We will include provisions
as to settlement upon conversion or exchange and whether conversion or exchange is mandatory, at the option of the holder or at our option.
We may include provisions pursuant to which the number of shares of our common stock that the holders of the series of debt securities
receive would be subject to adjustment.
Consolidation, Merger and Sale of Assets
We may not consolidate with
or merge with or into, or convey, transfer or lease all or substantially all of our properties and assets to any person, which we refer
to as a successor person, unless:
| · | we are the surviving corporation or the successor person (if other than us) is a corporation organized
and validly existing under the laws of any U.S. domestic jurisdiction and expressly assumes our obligations on the debt securities and
under the indenture; and |
| · | immediately after giving effect to the transaction, no Default or Event of Default, shall have occurred
and be continuing. |
Notwithstanding the above,
any of our subsidiaries may consolidate with, merge into or transfer all or part of its properties to us.
Events of Default
“Event of Default”
means with respect to any series of debt securities, any of the following:
| · | default in the payment of any interest upon any debt security of that series when it becomes due and payable,
and continuance of such default for a period of 30 days (unless the entire amount of the payment is deposited by us with the trustee or
with a paying agent prior to the expiration of the 30-day period); |
| · | default in the payment of principal of any security of that series at its maturity; |
| · | default in the performance or breach of any other covenant or warranty by us in the indenture (other than
a covenant or warranty that has been included in the indenture solely for the benefit of a series of debt securities other than that series),
which default continues uncured for a period of 60 days after we receive written notice from the trustee, or we and the trustee receive
written notice from the holders of not less than 25% in principal amount of the outstanding debt securities of that series as provided
in the indenture; |
| · | certain voluntary or involuntary events of bankruptcy, insolvency or reorganization of us; and |
| · | any other Event of Default provided with respect to debt securities of that series that is described in
the applicable prospectus supplement. |
No Event of Default with
respect to a particular series of debt securities (except as to certain events of bankruptcy, insolvency or reorganization) necessarily
constitutes an Event of Default with respect to any other series of debt securities. The occurrence of certain Events of Default or an
acceleration under the indenture may constitute an event of default under certain indebtedness of ours or our subsidiaries outstanding
from time to time.
We will provide the trustee
written notice of any Default or Event of Default within 30 days of becoming aware of the occurrence of such Default or Event of Default,
which notice will describe in reasonable detail the status of such Default or Event of Default and what action we are taking or propose
to take in respect thereof.
If an Event of Default with
respect to debt securities of any series at the time outstanding occurs and is continuing, then the trustee or the holders of not less
than 25% in principal amount of the outstanding debt securities of that series may, by a notice in writing to us (and to the trustee if
given by the holders), declare to be due and payable immediately the principal of (or, if the debt securities of that series are discount
securities, that portion of the principal amount as may be specified in the terms of that series) and accrued and unpaid interest, if
any, on all debt securities of that series. In the case of an Event of Default resulting from certain events of bankruptcy, insolvency
or reorganization, the principal (or such specified amount) of and accrued and unpaid interest, if any, on all outstanding debt securities
will become and be immediately due and payable without any declaration or other act on the part of the trustee or any holder of outstanding
debt securities. At any time after a declaration of acceleration with respect to debt securities of any series has been made, but before
a judgment or decree for payment of the money due has been obtained by the trustee, the holders of a majority in principal amount of the
outstanding debt securities of that series may rescind and annul the acceleration if all Events of Default, other than the non-payment
of accelerated principal and interest, if any, with respect to debt securities of that series, have been cured or waived as provided in
the indenture. We refer you to the prospectus supplement relating to any series of debt securities that are discount securities for the
particular provisions relating to acceleration of a portion of the principal amount of such discount securities upon the occurrence of
an Event of Default.
The indenture provides that
the trustee may refuse to perform any duty or exercise any of its rights or powers under the indenture unless the trustee receives indemnity
satisfactory to it against any cost, liability or expense which might be incurred by it in performing such duty or exercising such right
or power. Subject to certain rights of the trustee, the holders of a majority in principal amount of the outstanding debt securities of
any series will have the right to direct the time, method and place of conducting any proceeding for any remedy available to the trustee
or exercising any trust or power conferred on the trustee with respect to the debt securities of that series.
No holder of any debt security
of any series will have any right to institute any proceeding, judicial or otherwise, with respect to the indenture or for the appointment
of a receiver or trustee, or for any remedy under the indenture, unless:
| · | that holder has previously given to the trustee written notice of a continuing Event of Default with respect
to debt securities of that series; and |
| · | the holders of not less than 25% in principal amount of the outstanding debt securities of that series
have made written request, and offered indemnity or security satisfactory to the trustee, to the trustee to institute the proceeding as
trustee, and the trustee has not received from the holders of not less than a majority in principal amount of the outstanding debt securities
of that series a direction inconsistent with that request and has failed to institute the proceeding within 60 days. |
Notwithstanding any other
provision in the indenture, the holder of any debt security will have an absolute and unconditional right to receive payment of the principal
of, premium and any interest on that debt security on or after the due dates expressed in that debt security and to institute suit for
the enforcement of payment.
The indenture requires us,
within 120 days after the end of our fiscal year, to furnish to the trustee a statement as to compliance with the indenture. If a Default
or Event of Default occurs and is continuing with respect to the securities of any series and if it is known to a responsible officer
of the trustee, the trustee shall send to each securityholder of the securities of that series notice of a Default or Event of Default
within 90 days after it occurs or, if later, after a responsible officer of the trustee has knowledge of such Default or Event of Default.
The indenture provides that the trustee may withhold notice to the holders of debt securities of any series of any Default or Event of
Default (except in payment on any debt securities of that series) with respect to debt securities of that series if the trustee determines
in good faith that withholding notice is in the interest of the holders of those debt securities.
Modification and Waiver
We and the trustee may modify,
amend or supplement the indenture or the debt securities of any series without the consent of any holder of any debt security:
| · | to cure any ambiguity, defect or inconsistency; |
| · | to comply with covenants in the indenture described above under the heading “Consolidation, Merger
and Sale of Assets”; |
| · | to provide for uncertificated securities in addition to or in place of certificated securities; |
| · | to add guarantees with respect to debt securities of any series or secure debt securities of any series; |
| · | to surrender any of our rights or powers under the indenture; |
| · | to add covenants or events of default for the benefit of the holders of debt securities of any series; |
| · | to comply with the applicable procedures of the applicable depositary; |
| · | to make any change that does not adversely affect the rights of any holder of debt securities; |
| · | to provide for the issuance of and establish the form and terms and conditions of debt securities of any
series as permitted by the indenture; |
| · | to effect the appointment of a successor trustee with respect to the debt securities of any series and
to add to or change any of the provisions of the indenture to provide for or facilitate administration by more than one trustee; or |
| · | to comply with requirements of the SEC in order to effect or maintain the qualification of the indenture
under the Trust Indenture Act. |
We may also modify and amend
the indenture with the consent of the holders of at least a majority in principal amount of the outstanding debt securities of each series
affected by the modifications or amendments. We may not make any modification or amendment without the consent of the holders of each
affected debt security then outstanding if that amendment will:
| · | reduce the amount of debt securities whose holders must consent to an amendment, supplement or waiver; |
| · | reduce the rate of or extend the time for payment of interest (including default interest) on any debt
security; |
| · | reduce the principal of or premium on or change the fixed maturity of any debt security or reduce the
amount of, or postpone the date fixed for, the payment of any sinking fund or analogous obligation with respect to any series of debt
securities; |
| · | reduce the principal amount of discount securities payable upon acceleration of maturity; |
| · | waive a default in the payment of the principal of, premium or interest on any debt security (except a
rescission of acceleration of the debt securities of any series by the holders of at least a majority in aggregate principal amount of
the then outstanding debt securities of that series and a waiver of the payment default that resulted from such acceleration); |
| · | make the principal of or premium or interest on any debt security payable in currency other than that
stated in the debt security; |
| · | make any change to certain provisions of the indenture relating to, among other things, the right of holders
of debt securities to receive payment of the principal of, premium and interest on those debt securities and to institute suit for the
enforcement of any such payment and to waivers or amendments; or |
| · | waive a redemption payment with respect to any debt security. |
Except for certain specified
provisions, the holders of at least a majority in principal amount of the outstanding debt securities of any series may on behalf of the
holders of all debt securities of that series waive our compliance with provisions of the indenture. The holders of a majority in principal
amount of the outstanding debt securities of any series may on behalf of the holders of all the debt securities of such series waive any
past default under the indenture with respect to that series and its consequences, except a default in the payment of the principal of,
premium or any interest on any debt security of that series; provided, however, that the holders of a majority in principal amount of
the outstanding debt securities of any series may rescind an acceleration and its consequences, including any related payment default
that resulted from the acceleration.
Defeasance of Debt Securities and Certain Covenants
in Certain Circumstances
Legal Defeasance
The indenture provides that,
unless otherwise provided by the terms of the applicable series of debt securities, we may be discharged from any and all obligations
in respect of the debt securities of any series (subject to certain exceptions). We will be so discharged upon the irrevocable deposit
with the trustee, in trust, of money and/or U.S. government obligations or, in the case of debt securities denominated in a single currency
other than U.S. dollars, government obligations of the government that issued or caused to be issued such currency, that, through the
payment of interest and principal in accordance with their terms, will provide money or U.S. government obligations in an amount sufficient
in the opinion of a nationally recognized firm of independent public accountants or investment bank to pay and discharge each installment
of principal, premium and interest on and any mandatory sinking fund payments in respect of the debt securities of that series on the
stated maturity of those payments in accordance with the terms of the indenture and those debt securities.
This discharge may occur
only if, among other things, we have delivered to the trustee an opinion of counsel stating that we have received from, or there has been
published by, the United States Internal Revenue Service a ruling or, since the date of execution of the indenture, there has been a change
in the applicable United States federal income tax law, in either case to the effect that, and based thereon such opinion shall confirm
that, the holders of the debt securities of that series will not recognize income, gain or loss for United States federal income tax purposes
as a result of the deposit, defeasance and discharge and will be subject to United States federal income tax on the same amounts and in
the same manner and at the same times as would have been the case if the deposit, defeasance and discharge had not occurred.
Defeasance of Certain
Covenants
The indenture provides that,
unless otherwise provided by the terms of the applicable series of debt securities, upon compliance with certain conditions:
| · | we may omit to comply with the covenant described under the heading “Consolidation, Merger and Sale
of Assets” and certain other covenants set forth in the indenture, as well as any additional covenants which may be set forth in
the applicable prospectus supplement; and |
| · | any omission to comply with those covenants will not constitute a Default or an Event of Default with
respect to the debt securities of that series. |
We refer to this as covenant
defeasance. The conditions include:
| · | depositing with the trustee money and/or U.S. government obligations or, in the case of debt securities
denominated in a single currency other than U.S. dollars, government obligations of the government that issued or caused to be issued
such currency, that, through the payment of interest and principal in accordance with their terms, will provide money in an amount sufficient
in the opinion of a nationally recognized firm of independent public accountants or investment bank to pay and discharge each installment
of principal of, premium and interest on and any mandatory sinking fund payments in respect of the debt securities of that series on the
stated maturity of those payments in accordance with the terms of the indenture and those debt securities; |
| · | such deposit will not result in a breach or violation of, or constitute a default under the indenture
or any other agreement to which we are a party; |
| · | no Default or Event of Default with respect to the applicable series of debt securities shall have occurred
or is continuing on the date of such deposit; and |
| · | delivering to the trustee an opinion of counsel to the effect that we have received from, or there has
been published by, the United States Internal Revenue Service a ruling or, since the date of execution of the indenture, there has been
a change in the applicable United States federal income tax law, in either case to the effect that, and based thereon such opinion shall
confirm that, the holders of the debt securities of that series will not recognize income, gain or loss for United States federal income
tax purposes as a result of the deposit and related covenant defeasance and will be subject to United States federal income tax on the
same amounts and in the same manner and at the same times as would have been the case if the deposit and related covenant defeasance had
not occurred. |
No Personal Liability of Directors, Officers,
Employees or Stockholders
None of our past, present
or future directors, officers, employees or stockholders, as such, will have any liability for any of our obligations under the debt securities
or the indenture or for any claim based on, or in respect or by reason of, such obligations or their creation. By accepting a debt security,
each holder waives and releases all such liability. This waiver and release is part of the consideration for the issue of the debt securities.
However, this waiver and release may not be effective to waive liabilities under U.S. federal securities laws, and it is the view of the
SEC that such a waiver is against public policy.
Governing Law
The indenture and the debt
securities, including any claim or controversy arising out of or relating to the indenture or the securities, will be governed by the
laws of the State of New York.
The indenture will provide
that we, the trustee and the holders of the debt securities (by their acceptance of the debt securities) irrevocably waive, to the fullest
extent permitted by applicable law, any and all right to trial by jury in any legal proceeding arising out of or relating to the indenture,
the debt securities or the transactions contemplated thereby. The indenture will provide that any legal suit, action or proceeding arising
out of or based upon the indenture or the transactions contemplated thereby may be instituted in the federal courts of the United States
of America located in the City of New York or the courts of the State of New York in each case located in the City of New York, and we,
the trustee and the holder of the debt securities (by their acceptance of the debt securities) irrevocably submit to the non-exclusive
jurisdiction of such courts in any such suit, action or proceeding. The indenture will further provide that service of any process, summons,
notice or document by mail (to the extent allowed under any applicable statute or rule of court) to such party’s address set
forth in the indenture will be effective service of process for any suit, action or other proceeding brought in any such court. The indenture
will further provide that we, the trustee and the holders of the debt securities (by their acceptance of the debt securities) irrevocably
and unconditionally waive any objection to the laying of venue of any suit, action or other proceeding in the courts specified above and
irrevocably and unconditionally waive and agree not to plead or claim any such suit, action or other proceeding has been brought in an
inconvenient forum.
DESCRIPTION
OF CAPITAL STOCK
The following is a description of our capital
stock and certain provisions of our amended and restated articles of incorporation, amended and restated bylaws and certain provisions
of applicable law. The following is only a summary and is qualified by applicable law and by the provisions of our amended and restated
articles of incorporation and amended and restated bylaws, copies of which are included as exhibits to the registration statement of which
this prospectus forms a part. We are incorporated in the State of Nevada The rights of our stockholders are generally covered by Nevada
law and our amended and restated articles of incorporation and amended and restated bylaws. The terms of our capital stock are therefore
subject to Nevada law.
Our authorized capital stock consists of 300,000,000
shares of common stock, $0.00001 par value per share, and 10,000,000 shares of preferred stock, $0.00001 par value per share. As of March 1,
2023, 215,704,036 shares of common stock were issued and outstanding and no shares of preferred stock were issued and outstanding.
Common Stock
Our common stock is traded on the Nasdaq Capital
Market under the symbol “XXII.” Holders of our common stock are entitled to one vote for each share held on all matters submitted
to a vote of stockholders and do not have cumulative voting rights. Holders of common stock are entitled to receive ratably such dividends,
if any, as may be declared by the board of directors out of funds legally available therefore, subject to a preferential dividend right
of outstanding preferred stock. Upon the liquidation, dissolution or our winding up, the holders of common stock are entitled to receive
ratably our net assets available after the payment of all debts and other liabilities and subject to the prior rights of any outstanding
preferred stock. The rights, preferences and privileges of holders of our common stock are subject to, and may be adversely affected by
the rights of the holders any series of preferred stock that we may designate and issue in the future.
Preferred Stock
Under the terms of our amended and restated articles
of incorporation, the board of directors is authorized, subject to any limitations prescribed by law, without stockholder approval, to
issue such shares of preferred stock in one or more series. Each such series of preferred stock shall have such rights, preferences, privileges
and restrictions, including voting rights, dividend rights, conversion rights, redemption privileges and liquidation preferences, as shall
be determined by the board of directors.
The purpose of authorizing the board of directors
to issue preferred stock and determine its rights and preferences is to eliminate delays associated with a stockholder vote on specific
issuances. The issuance of preferred stock, while providing desirable flexibility in connection with possible acquisitions and other corporate
purposes, could have the effect of making it more difficult for a third part to acquire, or of discouraging a third party from acquiring,
a majority of our outstanding voting stock. We have no present plans to issue any additional shares of preferred stock.
The effects of issuing preferred stock could include
one or more of the following:
| |
· |
decreasing the amount of earnings and assets available for distribution to holders of common stock; |
| |
· |
restricting dividends on the common stock; |
| |
· |
diluting the voting power of the common stock; |
| |
· |
impairing the liquidation rights of the common stock; or |
| |
· |
delaying, deferring or preventing changes in our control or management. |
As of the date of this prospectus, there were no
shares of preferred stock outstanding.
Stock Options and Restricted Stock
As of March 1, 2023 we had outstanding options
to purchase a total of 4,912,105 shares of common stock at a weighted average exercise price of $1.67 per share and 4,010,241 shares of
unvested restricted stock or restricted stock units. As of March 1, 2023 an additional 4,484,702 shares of common stock were available
for future award grants under our stock incentive plan.
Warrants
July 2022 Warrants
As of March 1, 2023, the Company has outstanding
warrants to purchase up to 17,073,175 shares of common stock. The warrants are currently exercisable at an exercise price of $2.05 per
share, subject to certain adjustments, and expire on July 25, 2027. A holder of warrants will have the right to exercise the warrants
on a “cashless” basis if there is no effective registration statement registering the resale of the warrant shares. Subject
to limited exceptions, a holder of warrants will not have the right to exercise any portion of its warrants if the holder, together with
its affiliates, would beneficially own in excess of 4.99% (or 9.99% at the election of the holder prior to the date of issuance) of the
number of shares of our common stock outstanding immediately after giving effect to such exercise, provided that the holder may increase
or decrease the beneficial ownership limitation up to 9.99%. Any increase in the beneficial ownership limitation shall not be effective
until 61 days following notice of such change to us. Except as otherwise provided in the warrants or by virtue of such holder’s
ownership of shares of our common stock, the holders of the warrants do not have the rights or privileges of holders of our common stock,
including any voting rights, until they exercise their warrants.
In the event of any fundamental transaction, as
described in the warrants and generally including any merger with or into another entity, sale of all or substantially all of our assets,
tender offer or exchange offer, or reclassification of our shares of common stock, then upon any subsequent exercise of a warrant, the
holder will have the right to receive as alternative consideration, for each share of common stock that would have been issuable upon
such exercise immediately prior to the occurrence of such fundamental transaction, the number of shares of common stock of the successor
or acquiring corporation of our company, if it is the surviving corporation, and any additional consideration receivable upon or as a
result of such transaction by a holder of the number of shares of common stock for which the warrant is exercisable immediately prior
to such event. Notwithstanding the foregoing, in the event of a fundamental transaction, the holders of the warrants have the right to
require us or a successor entity to redeem the warrants for cash in the amount of the Black Scholes Value (as defined in each warrant)
of the unexercised portion of the warrants concurrently with or within 5 days following the consummation of a fundamental transaction.
However, in the event of a fundamental transaction which is not in our control, including a fundamental transaction not approved by our
board of directors, the holders of the warrants will only be entitled to receive from us or our successor entity, as of the date of consummation
of such fundamental transaction the same type or form of consideration (and in the same proportion), at the Black Scholes Value of the
unexercised portion of the warrant, that is being offered and paid to the holders of our common stock in connection with the fundamental
transaction, whether that consideration is in the form of cash, stock or any combination of cash and stock, or whether the holders of
our common stock are given the choice to receive alternative forms of consideration in connection with the fundamental transaction.
There is no established public trading market for
the warrants and we do not expect a market to develop. In addition, we do not intend to list the warrants on the Nasdaq Capital Market,
any other national securities exchange or any other nationally recognized trading system.
March 2023 Warrants
On March 3, 2023, we
issued warrants to purchase up to 5,000,000 shares of our common stock. The warrants are exercisable for five years from September 3,
2023, at an exercise price of $1.275 per share, subject, with certain exceptions, to adjustments in the event of stock splits, dividends,
subsequent dilutive offerings and certain fundamental transactions. We are obligated to register the shares of common stock issuable upon
exercise of the warrants.
In addition, on March 3,
2023, we issued warrants to purchase up to 675,000 shares of our common stock. The warrants are exercisable for seven years from September 3,
2023, at an exercise price of $0.855 per share, subject, with certain exceptions, to adjustments in the event of stock splits, dividends,
subsequent dilutive offerings and certain fundamental transactions.
There is no established public
trading market for the warrants and we do not expect a market to develop. In addition, we do not intend to list the warrants on the Nasdaq
Capital Market, any other national securities exchange or any other nationally recognized trading system.
Anti-Takeover Provisions Under Nevada Law.
Combinations
with Interested Stockholder. Sections 78.411-78.444, inclusive, of the Nevada Revised Statutes (NRS) contain provisions
governing combinations with an interested stockholder. For purposes of the NRS, "combinations" include: (i) any merger
or consolidation of a Nevada corporation or any subsidiary of a Nevada corporation with the interested stockholder or any other entity,
whether or not itself is an interested stockholder of the Nevada corporation, which is, or after and as a result of the merger or consolidation
would be, an affiliate or associate of the interested stockholder; (ii) any sale, lease, exchange mortgage, pledge, transfer or other
disposition, in one transaction or a series of transactions, to or with the interested stockholder or any affiliate or associate of the
interested stockholder of assets of the Nevada corporation or any subsidiary of the Nevada corporation (x) having an aggregate market
value equal to more than 5% of the aggregate market value of all of the consolidated assets of the Nevada corporation, (y) having
an aggregate market value equal to more than 5% of the aggregate market value of all the outstanding voting shares of the Nevada corporation,
or (z) representing more than 10% of the earning power or net income of the Nevada corporation (determined on a consolidated basis);
(iii) the issuance or transfer by the Nevada corporation or any subsidiary of the Nevada corporation, in one transaction or a series
of transactions, of any shares of the Nevada corporation or any subsidiary of the Nevada corporation that have an aggregate market value
equal to 5% or more of the aggregate market value of all the outstanding voting shares of the Nevada corporation to the interested stockholder
or any affiliate or associate of the interested stockholder except under the exercise of warrants or rights to purchase shares offered,
or a dividend or distribution paid or made, pro rata to all stockholders of the Nevada corporation; (iv) the adoption of any plan
or proposal for the liquidation or dissolution of the Nevada corporation under any agreement, arrangement or understanding, whether or
not in writing, with the interested stockholder or affiliate or associate of the interested stockholder; (v) except for transactions
that would not constitute a combination pursuant to subsection (iii) above, any reclassification of securities (including, without
limitation, share splits, share dividend or other distribution of shares with respect to other shares, or any issuance of new shares in
exchange for a proportionately greater number of old shares), any recapitalization of the Nevada corporation, any merger or consolidation
of the Nevada corporation with any of its subsidiaries, or any other transaction, whether or not with or into or otherwise involving the
interested stockholder, under any agreement, arrangement or understanding, whether or not in writing, with the interested stockholder
or any affiliate or associate of the interested stockholder, which has the immediate and proximate effect of increasing the proportionate
share of the outstanding shares of any class or series of voting shares or securities convertible into voting shares of the Nevada corporation
or any subsidiary of the Nevada corporation which is beneficially owned by the interested stockholder or any affiliate or associate of
the interested stockholder, except as a result of immaterial changes because of adjustments of fractional shares; and (vi) any receipt
by the interested stockholder or any affiliate or associate of the interested stockholder of the benefit, directly or indirectly, except
proportionately as a stockholder of the Nevada corporation, of any loan, advance, guarantee, pledge or other financial assistance or any
tax credit or other tax advantage provided by or through the Nevada corporation.
For purposes of the NRS, an "interested stockholder"
is defined to include any person, other than the Nevada corporation or any subsidiary of the Nevada corporation, who is: (a) a beneficial
owner, directly or indirectly, of 10% or more of the voting power of the outstanding voting shares of the Nevada corporation or (b) an
affiliate or associate of the Nevada corporation and was, at any time within two years immediately before the date in question, the beneficial
owner, directly or indirectly, of 10% or more of the voting power of the then-outstanding shares of the Nevada corporation.
Subject to certain exceptions, the provisions of
the NRS statute governing combinations with interested stockholders provide that a Nevada corporation may not engage in a combination
with an interested stockholder for two years after the date that the person first became an interested stockholder unless the combination
meets all of the requirements of the articles of incorporation of the Nevada corporation and (i) the combination or the transaction
by which the person first became an interested stockholder is approved by the board of directors before the person first became an interested
stockholder or (ii) during the two-year period, the transaction is approved by the board and by 60% of the disinterested stockholders
at an annual or special meeting of the stockholders.
After such two-year period, corporations subject
to these statutes may not engage in specified business combinations and transactions unless the combination meets all of the requirements
of the articles of incorporation of the Nevada corporation and: (i) the business combination or transaction by which the person first
became an interested stockholder is approved by the board of directors before the stockholder became an interested stockholder; (ii) the
business combination is approved by a majority of the outstanding voting power (excluding the shares held by the interested stockholder
or any affiliate or associate of the interested stockholder); or (iii) the combination meets the requirements of 78.411 through 78.444
of the NRS, inclusive.
The NRS allows a corporation to "opt out"
of NRS 78.411 through 78.444, inclusive, by providing in such corporation's original articles of incorporation or bylaws that such statutes
do not apply to the corporation. Unless certain limited exceptions apply, corporations cannot opt out of such statutes by amending their
articles of incorporation or bylaws. We have not opted out of such statutes.
Control
Share Acquisitions. The NRS also contains a "control share acquisitions statute." If applicable to a Nevada
corporation, this statute restricts the voting rights of certain stockholders referred to as "acquiring persons," that acquire
or offer to acquire, directly or indirectly, ownership of a "controlling interest" in the outstanding voting stock of an "issuing
corporation." For purposes of these provisions (i) a "controlling interest" means, with certain exceptions, the ownership
of outstanding voting stock sufficient to enable the acquiring person to exercise one-fifth or more but less than one-third, one-third
or more but less than a majority, or a majority or more of all voting power in the election of directors and (ii) an "issuing
corporation" means a Nevada corporation, as of any date, that has 200 or more stockholders of record, at least 100 of whom have had
addresses in Nevada appearing on the stock ledger of the corporation at all times during the 90 days immediately preceding such date,
and which does business in Nevada directly or through an affiliated corporation. The voting rights of an acquiring person in the affected
shares will be restored only if such restoration is approved by the holders of a majority of the voting power of the corporation, and
if the acquisition would adversely alter or change any preference or any relative or other right given to any other class or series of
outstanding shares, the holders of a majority of each class affected (excluding the shares held by the acquiring person) at an annual
or special meeting of the stockholders.
The NRS allows a corporation to "opt out"
of the control share acquisitions statute by providing in such corporation's articles of incorporation or bylaws, in effect on the 10th
day following the acquisition of a controlling interest by an acquiring person, that the control share acquisitions statute does not apply
to the corporation or to an acquisition of a controlling interest specifically by types of existing or future stockholders, whether or
not identified. We have not opted out of the control share acquisitions statute.
Liability and Indemnification of Directors and Officers
NRS Sections 78.7502 and 78.751 provide us with
the power to indemnify any of our directors, officers, employees or agents, or any person who serves or served at the corporation’s
request as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise (for purposes
of this section, the “Indemnitee” or “Indemnitees”) against expenses, including attorneys’ fees, actually
and reasonably incurred related to any threatened, pending or completed action, suit or proceeding (whether civil, criminal, administrative
or investigative) arising by reason of an Indemnitee’s status as a director, officer employee or agent of the corporation if: (i) the
Indemnitee is not liable for breach of fiduciary duties to the corporation involving intentional misconduct, fraud or knowing violation
of law; (ii) the Indemnitee conducted himself or herself in good faith and reasonably believes that his or her conduct was in, or
not opposed to, our best interests; or (iii) in a criminal action, the Indemnitee must not have had reasonable cause to believe that
his or her conduct was unlawful. NRS Section 78.751 requires us to indemnify any Indemnitee for any expenses referenced above if
the Indemnitee has been successful on the merits or otherwise in defense of the foregoing actions, suits or proceedings.
Under NRS Section 78.7502, any discretionary
indemnification, unless ordered by a court or advanced by the corporation in accordance with NRS Section 78.751(2), can only occur
if deemed proper by (i) the stockholders; (ii) a majority vote of a quorum consisting of disinterested directors; or (iii) an
independent counsel’s written legal opinion (if such an approach is approved by a majority vote of a quorum consisting of disinterested
directors or if a quorum consisting of disinterested directors cannot be obtained). Under NRS Section 78.751(2), advances for expenses
may be made by agreement if the Indemnitee affirms in writing that he or she believes that he or she has met the statutory standards and
will personally repay the expenses if a court of competent jurisdiction determines that such Indemnitee did not meet the statutory standards.
Our amended and restated bylaws include an indemnification
provision under which we have the power to indemnify, to the extent permitted under Nevada law, our current and former directors and officers,
or any person who serves or served at our request for our benefit as a director or officer of another corporation or our representative
in a partnership, joint venture, trust or other enterprise, against all expenses, liability and loss reasonably incurred by reason of
being or having been a director, officer or representative of ours or any of our subsidiaries. We may make advances for expenses upon
receipt of an undertaking by or on behalf of the director or officer to repay the amount if it is ultimately determined by a court of
competent jurisdiction that he, she or it is not entitled to be indemnified by us.
Our amended and restated articles of incorporation
provides that we shall indemnify directors and officers to the fullest extent permitted by the NRS. Our amended and restated articles
of incorporation also provide a limitation of liability such that no director or officer shall be personally liable to us or any of our
stockholders to the fullest extent permitted by the NRS.
Insofar as indemnification for liabilities arising
under the Securities Act of 1933, as amended (the “Securities Act”) may be permitted to directors, officers and controlling
persons of ours under Nevada law or otherwise, we have been advised that the opinion of the SEC is that such indemnification is against
public policy as expressed in the Securities Act and is, therefore, unenforceable. In the event a claim for indemnification against such
liabilities (other than payment by us for expenses incurred or paid by a director, officer or controlling person of ours in successful
defense of any action, suit, or proceeding) is asserted by a director, officer or controlling person in connection with the securities
being registered, we will, unless in the opinion of our legal counsel the matter has been settled by controlling precedent, submit to
a court of appropriate jurisdiction the question of whether such indemnification by our company is against public policy in the Securities
Act and will be governed by the final adjudication of such issue.
Nasdaq Capital Market Listing
Our common stock is listed on the Nasdaq Capital
Market under the symbol “XXII.”
Transfer Agent and Registrar
The
transfer agent and registrar for our common stock is Continental Stock Transfer & Trust Company.
DESCRIPTION
OF WARRANTS
We may issue other warrants in the future for the
purchase of debt securities, common stock, preferred stock, units or other securities. Warrants may be issued independently or together
with debt securities, common stock, preferred stock or units offered by any prospectus supplement and/or other offering material and may
be attached to or separate from any such offered securities. Each series of warrants will be issued under a separate warrant agreement
to be entered into between us and a bank or trust company, as warrant agent, provided that we may also act as warrant agent and enter
into warrant agreements directly with the purchasers of securities offered pursuant to this prospectus. In each case, the terms of the
warrants will be set forth in the prospectus supplement and/or other offering material relating to the particular issue of warrants. The
warrant agent, if any, will act solely as our agent in connection with the warrants and will not assume any obligation or relationship
of agency or trust for or with any holders of warrants or beneficial owners of warrants.
The following summary of certain provisions of
the warrants we may issue in the future does not purport to be complete and is subject to, and is qualified in its entirety by reference
to, all provisions of the warrant agreements.
Reference is made to the prospectus supplement
and/or other offering material relating to the particular issue of warrants offered pursuant to such prospectus supplement and/or other
offering material for the terms of and information relating to such warrants, including, where applicable:
| · | the designation, aggregate principal amount, currencies, denominations and terms of the series of debt securities purchasable upon
exercise of warrants to purchase debt securities and the price at which such debt securities may be purchased upon such exercise; |
| · | the number of shares of common stock or preferred stock purchasable upon the exercise of warrants and the price at which such number
of shares of common stock or preferred stock may be purchased upon such exercise; |
| · | the designation and number of units of other securities purchasable upon the exercise of warrants to purchase other securities and
the price at which such number of units of such other securities may be purchased upon such exercise; |
| · | the date on which the right to exercise such warrants shall commence and the date on which such right shall expire; |
| · | U.S. federal income tax consequences applicable to such warrants; |
| · | the amount of warrants outstanding as of the most recent practicable date; and |
| · | any other terms of such warrants. |
Warrants will be issued in registered form only.
The exercise price for warrants will be subject to adjustment in accordance with the applicable prospectus supplement and/or other offering
material.
Each warrant will entitle the holder thereof to
purchase such principal amount of debt securities or such number of shares of common stock, preferred stock, units or other securities
at such exercise price as shall in each case be set forth in, or calculable from, the prospectus supplement and/or other offering material
relating to the warrants, which exercise price may be subject to adjustment upon the occurrence of certain events as set forth in such
prospectus supplement and/or other offering material. After the close of business on the expiration date, or such later date to which
such expiration date may be extended by us, unexercised warrants will become void. The place or places where, and the manner in which,
warrants may be exercised shall be specified in the prospectus supplement and/or other offering material relating to such warrants.
Prior to the exercise of any warrants to purchase
debt securities, common stock, preferred stock, units or other securities, holders of such warrants will not have any of the rights of
holders of the underlying securities, as the case may be, purchasable upon such exercise, including the right to receive payments of principal
of, premium, if any, or interest, if any, on the debt securities purchasable upon such exercise or to enforce covenants in the applicable
indenture, or to receive payments of dividends, if any, on the common stock purchasable upon such exercise, or to exercise any applicable
right to vote.
DESCRIPTION
OF SUBSCRIPTION RIGHTS
We may issue subscription rights to purchase debt
securities, common stock, preferred stock, warrants, units other securities described in this prospectus or any combination thereof. These
subscription rights may be issued independently or together with any other security offered by us and may or may not be transferable by
the stockholder receiving the subscription rights in such offering. In connection with any offering of subscription rights, we may enter
into a standby arrangement with one or more underwriters or other investors pursuant to which the underwriters or other investors may
be required to purchase any securities remaining unsubscribed for after such offering.
To the extent appropriate, the applicable prospectus
supplement will describe the specific terms of the subscription rights to purchase shares of our securities offered thereby, including
the following:
| · | the date of determining the stockholders entitled to the rights distribution; |
| · | the price, if any, for the subscription rights; |
| · | the exercise price payable for the debt securities, common stock, preferred stock, warrants, units or other securities upon the exercise
of the subscription right; |
| · | the number of subscription rights issued to each stockholder; |
| · | the amount of debt securities, common stock, preferred stock, warrants, units or other securities that may be purchased per each subscription
right; |
| · | any provisions for adjustment of the amount of securities receivable upon exercise of the subscription rights or of the exercise price
of the subscription rights; |
| · | the extent to which the subscription rights are transferable; |
| · | the date on which the right to exercise the subscription rights shall commence, and the date on which the subscription rights shall
expire; |
| · | the extent to which the subscription rights may include an over-subscription privilege with respect to unsubscribed securities; |
| · | the material terms of any standby underwriting or purchase arrangement entered into by us in connection with the offering of subscription
rights; |
| · | any applicable federal income tax considerations; and |
| · | any other terms of the subscription rights, including the terms, procedures and limitations relating to the transferability, exchange
and exercise of the subscription rights. |
DESCRIPTION
OF SECURITIES PURCHASE CONTRACTS
We may issue securities purchase contracts, which
consist of contracts obligating holders to purchase from us, and obligating us to sell to the holders, a specified number of shares of
common stock, preferred stock, warrants, units, debt securities or other securities at a future date or dates, which we refer to in this
prospectus as “securities purchase contracts.” The terms and conditions for any purchase and sale rights or obligations, as
well as the price per share of the underlying securities (if applicable) and the number or value of the underlying securities, may be
fixed at the time the securities purchase contracts are issued or may be determined by reference to a specific formula set forth in the
securities purchase contracts.
The securities purchase contracts may be issued
separately or as part of units, other securities or debt obligations of third parties, including U.S. treasury securities, securing the
holders’ obligations to purchase the securities under the securities purchase contracts. The securities purchase contracts may require
holders to secure their obligations under the securities purchase contracts in a specified manner. The securities purchase contracts also
may require us to make periodic payments to the holders thereof or vice versa, and those payments may be unsecured or refunded on some
basis.
The securities purchase contracts, and, if applicable,
collateral or depositary arrangements, relating to the securities purchase contracts, will be filed with the SEC in connection with the
offering of securities purchase contracts. The prospectus supplement and/or other offering material relating to a particular issue of
securities purchase contracts will describe the terms of those securities purchase contracts, including the following:
| · | if applicable, a discussion of material U.S. federal income tax considerations; and |
| · | any other information we think is important about the securities purchase contracts. |
DESCRIPTION
OF UNITS
As specified in the applicable prospectus supplement,
we may issue units consisting of one or more shares of common stock, shares of preferred stock, debt securities, warrants, subscription
rights and securities purchase contracts, or any combination of the foregoing.
The applicable prospectus supplement will specify
the following terms of the units:
| · | the terms of the underlying securities comprising the units, including whether and under what circumstances the underlying securities
may be traded separate of the units; |
| · | a description of the terms of any unit agreement governing the units (if any); |
| · | if appropriate, a discussion of material U.S. federal income tax considerations; and |
| · | a description of the provisions for the payment, settlement, transfer or exchange of the units. |
PLAN
OF DISTRIBUTION
We may sell securities in any one or more of the
following ways from time to time: (i) through agents; (ii) to or through underwriters; (iii) through brokers or dealers;
(iv) directly to purchasers, including through a specific bidding, auction or other process; (v) upon the exercise of subscription
rights that may be distributed to our stockholders; (vi) through a combination of any of these methods of sale or (vii) through
any other methods described in a prospectus supplement. The applicable prospectus supplement and/or other offering material will contain
the terms of the transaction, name or names of any underwriters, dealers, agents and the respective amounts of securities underwritten
or purchased by them, the initial public offering price of the securities, and the applicable agent’s commission, dealer’s
purchase price or underwriter’s discount. Any dealers and agents participating in the distribution of the securities may be deemed
to be underwriters, and compensation received by them on resale of the securities may be deemed to be underwriting discounts.
Any initial offering price, dealer purchase price,
discount or commission may be changed from time to time.
The securities may be distributed from time to
time in one or more transactions, at negotiated prices, at a fixed price or fixed prices (that may be subject to change), at market prices
prevailing at the time of sale, in at the market offerings, at various prices determined at the time of sale or at prices related to prevailing
market prices.
Offers to purchase securities may be solicited
directly by us or by agents designated by us from time to time. Any such agent may be deemed to be an underwriter, as that term is defined
in the Securities Act, of the securities so offered and sold.
If underwriters are utilized in the sale of any
securities in respect of which this prospectus is being delivered, such securities will be acquired by the underwriters for their own
account and may be resold from time to time in one or more transactions, including negotiated transactions, at fixed public offering prices
or at varying prices determined by the underwriters at the time of sale. Securities may be offered to the public either through underwriting
syndicates represented by managing underwriters or directly by one or more underwriters. If any underwriter or underwriters are utilized
in the sale of securities, unless otherwise indicated in the applicable prospectus supplement and/or other offering material, the obligations
of the underwriters are subject to certain conditions precedent, and that the underwriters will be obligated to purchase all such securities
if any are purchased.
If a dealer is utilized in the sale of the securities
in respect of which this prospectus is delivered, we will sell such securities to the dealer, as principal. The dealer may then resell
such securities to the public at varying prices to be determined by such dealer at the time of resale. Transactions through brokers or
dealers may include block trades in which brokers or dealers will attempt to sell shares as agent but may position and resell as principal
to facilitate the transaction or in crosses, in which the same broker or dealer acts as agent on both sides of the trade. Any such dealer
may be deemed to be an underwriter, as such term is defined in the Securities Act, of the securities so offered and sold. If we offer
securities in a subscription rights offering to our existing securityholders, we may enter into a standby underwriting agreement with
dealers, acting as standby underwriters. We may pay the standby underwriters a commitment fee for the securities they commit to purchase
on a standby basis. If we do not enter into a standby underwriting arrangement, we may retain a dealer-manager to manage a subscription
rights offering for us.
Offers to purchase securities may be solicited
directly by us and the sale thereof may be made directly to institutional investors or others, who may be deemed to be underwriters within
the meaning of the Securities Act with respect to any resale thereof.
If so indicated in the applicable prospectus supplement
and/or other offering material, we may authorize agents and underwriters to solicit offers by certain institutions to purchase securities
at the public offering price set forth in the applicable prospectus supplement and/or other offering material pursuant to delayed delivery
contracts providing for payment and delivery on the date or dates stated in the applicable prospectus supplement and/or other offering
material. Such delayed delivery contracts will be subject only to those conditions set forth in the applicable prospectus supplement and/or
other offering material.
Agents, underwriters and dealers may be entitled
under relevant agreements to indemnification against certain liabilities, including liabilities under the Securities Act, or to contribution
with respect to payments which such agents, underwriters and dealers may be required to make in respect thereof. The terms and conditions
of any indemnification or contribution will be described in the applicable prospectus supplement and/or other offering material.
We may also sell shares of our common stock through
various arrangements involving mandatorily or optionally exchangeable securities, and this prospectus may be delivered in connection with
those sales.
We may engage in at the market offerings into an
existing trading market in accordance with Rule 415(a)(4) under the Securities Act. To the extent that we make sales through
one or more underwriters or agents in at the market offerings, we will do so pursuant to the terms of a sales agency financing agreement
or other at the market offering arrangement between us and the underwriters or agents. If we engage in at the market sales pursuant to
any such agreement or arrangement, we will issue and sell our securities through one or more underwriters or agents, which may act on
an agency basis or a principal basis. During the term of any such agreement or arrangement, we may sell securities on a daily basis in
exchange transactions or otherwise as we agreement with the underwriters or agents. Any such agreement or arrangement will provide that
any securities sold will be sold at prices related to the then-prevailing market prices for our securities. Therefore, exact figures regarding
proceeds that will be raised or commissions to be paid cannot be determined at this time. Pursuant to the terms of the agreement or arrangement,
we may agree to sell, and the relevant underwriters or agents may agree to solicit offers to purchase blocks of our common stock. The
terms of any such agreement or arrangement will be set forth in more detail in the applicable prospectus supplement.
We may enter into derivative, sale or forward sale
transactions with third parties, or sell securities not covered by this prospectus to third parties in privately negotiated transactions.
If the applicable prospectus supplement and/or other offering material indicates, in connection with those transactions, the third parties
may sell securities covered by this prospectus and the applicable prospectus supplement and/or other offering material, including in short
sale transactions and by issuing securities not covered by this prospectus but convertible into, or exchangeable for or representing beneficial
interests in such securities covered by this prospectus, or the return of which is derived in whole or in part from the value of such
securities. The third parties may use securities received under derivative, sale or forward sale transactions, or securities pledged by
us or borrowed from us or others to settle those sales or to close out any related open borrowings of stock, and may use securities received
from us in settlement of those transactions to close out any related open borrowings of stock. The third party in such sale transactions
will be an underwriter and will be identified in the applicable prospectus supplement (or a post-effective amendment) and/or other offering
material.
Underwriters, broker-dealers or agents may receive
compensation in the form of commissions, discounts or concessions from us. Underwriters, broker-dealers or agents may also receive compensation
from the purchasers of shares for whom they act as agents or to whom they sell as principals, or both. Compensation as to a particular
underwriter, broker-dealer or agent might be in excess of customary commissions and will be in amounts to be negotiated in connection
with transactions involving shares. In effecting sales, broker-dealers may arrange for other broker-dealers to participate in the resales.
Each series of securities will be a new issue and,
other than the common stock, which is listed on the Nasdaq Capital Market, will have no established trading market. We may elect to list
any series of securities on an exchange, and in the case of the common stock, on any additional exchange, but, unless otherwise specified
in the applicable prospectus supplement and/or other offering material, we shall not be obligated to do so. No assurance can be given
as to the liquidity of the trading market for any of the securities.
Agents, underwriters and dealers may engage in
transactions with, or perform services for us and our respective subsidiaries in the ordinary course of business.
Any underwriter may engage in overallotment, stabilizing
transactions, short covering transactions and penalty bids in accordance with Regulation M under the Exchange Act. Overallotment involves
sales in excess of the offering size, which create a short position. Stabilizing transactions permit bids to purchase the underlying security
so long as the stabilizing bids do not exceed a specified maximum. Short covering transactions involve purchases of the securities in
the open market after the distribution is completed to cover short positions. Penalty bids permit the underwriters to reclaim a selling
concession from a dealer when the securities originally sold by the dealer are purchased in a covering transaction to cover short positions.
Those activities may cause the price of the securities to be higher than it would otherwise be. If commenced, the underwriters may discontinue
any of the activities at any time. An underwriter may carry out these transactions on the Nasdaq Capital Market, in the over-the-counter
market or otherwise.
The place and time of delivery for securities will
be set forth in the accompanying prospectus supplement and/or other offering material for such securities.
WHERE
YOU CAN FIND MORE INFORMATION
We file annual, quarterly and current reports,
proxy statements and other information with the SEC. The SEC maintains an internet site that contains reports, proxy and information
statements and other information regarding issuers, including ours, that file electronically with the SEC. The public can obtain any document
that we file electronically with the SEC at www.sec.gov.
We are “incorporating by reference”
specified documents that we file with the SEC, which means:
| · | incorporated documents are considered part of this prospectus; |
| · | we are disclosing important information to you by referring you to those documents; and |
| · | information we file with the SEC will automatically update and supersede information contained in this prospectus. |
We incorporate by reference the documents listed
below and any future filings we make with the SEC under Section 13(a), 13(c), 14 or 15(d) of the Exchange Act (i) after
the date of the registration statement on Form S-3 filed under the Securities Act with respect to securities offered by this prospectus
and prior to the effectiveness of such registration statement and (ii) after the date of this prospectus and before the end of the
offering of the securities pursuant to this prospectus:
| |
· |
Our Annual Report on Form 10-K for the fiscal year ended December 31, 2022 filed with the SEC on March 9, 2023; |
| · | The description of our common stock contained in or incorporated into
our Registration Statement on Form 8-A, filed August 12, 2021, and any amendment or report updating that description. |
Notwithstanding the foregoing, documents or portions
thereof containing information furnished under Items 2.02 and 7.01 of any Current Report on Form 8-K, including the related exhibits
under Item 9.01, are not incorporated by reference in this prospectus. Information in this prospectus supersedes related information in
the documents listed above, and information in subsequently filed documents supersedes related information in both this prospectus and
the incorporated documents.
We will provide, without charge to you, upon written
or oral request, a copy of any or all of the documents incorporated by reference in this prospectus, other than exhibits to those documents,
unless the exhibits are specifically incorporated by reference in those documents. Requests should be directed to our principal
executive offices at:
22nd Century Group, Inc.
500 Seneca Street, Suite 507,
Buffalo, New York 14204
(716) 270-1523
You can also find these filings on our website
at www.xxiicentury.com. We are not incorporating the information on our website other than these filings into this prospectus. You should
rely only on the information contained in this prospectus (including information incorporated by reference therein) and any free writing
prospectus that we may authorize to be delivered to you. We have not authorized anyone to provide you with different information. If anyone
provides you with different or inconsistent information, you should not rely on it. You should not assume that the information in this
prospectus is accurate as of any date other than the date on the front of those documents or that any document incorporated by reference
is accurate as of any date other than its filing date. You should not consider this prospectus to be an offer or solicitation relating
to the securities in any jurisdiction in which such an offer or solicitation relating to the securities is not authorized. Furthermore,
you should not consider this prospectus to be an offer or solicitation relating to the securities if the person making the offer or solicitation
is not qualified to do so, or if it is unlawful for you to receive such an offer or solicitation.
LEGAL
MATTERS
The validity of the securities offered by this
prospectus will be passed upon for us by Foley & Lardner LLP. The validity of the securities offered by this prospectus will
be passed upon for any underwriters or agents by counsel named in the applicable prospectus supplement. The opinions of Foley &
Lardner LLP and counsel for any underwriters or agents may be conditioned upon and may be subject to assumptions regarding future action
required to be taken by us and any underwriters, dealers or agents in connection with the issuance of any securities. The opinions of
Foley & Lardner LLP and counsel for any underwriters or agents may be subject to other conditions and assumptions, as indicated
in the prospectus supplement.
EXPERTS
The consolidated
financial statements incorporated in this Prospectus by reference to the Annual Report on Form 10-K for the year ended December 31,
2022 have been so incorporated in reliance on the report of Freed Maxick CPAs, P.C., an independent registered public accounting firm,
given on the authority of said firm as experts in auditing and accounting.
The
combined consolidated financial statements of GVB Biopharma, which appear in the Company’s Current Report on Form 8-K/A filed
with the Securities and Exchange Commission on July 20, 2022, incorporated herein by reference have been so incorporated in reliance
on the report of Armanino LLP, an independent registered public accounting firm.
PROSPECTUS SUPPLEMENT
June 19, 2023
22nd Century (AMEX:XXII)
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