Form 8-K/A
8-K/A — 22nd Century Group, Inc.
Accession: 0001493152-26-027870
Filed: 2026-06-09
Period: 2026-06-08
CIK: 0001347858
SIC: 2111 (CIGARETTES)
Item: Entry into a Material Definitive Agreement
Item: Unregistered Sales of Equity Securities
Item: Material Modifications to Rights of Security Holders
Item: Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year
Item: Financial Statements and Exhibits
Documents
8-K/A — form8-ka.htm (Primary)
EX-3.1 (ex3-1.htm)
EX-4.1 (ex4-1.htm)
EX-10.1 (ex10-1.htm)
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UNITED
STATES
SECURITIES
AND EXCHANGE COMMISSION
WASHINGTON,
D.C. 20549
FORM
8-K/A
(Amendment No. 1)
CURRENT
REPORT
Pursuant
to Section 13 or 15(d) of the
Securities
Exchange Act of 1934
Date
of Report (Date of earliest event reported): June 8, 2026
22nd
Century Group, Inc.
(Exact
Name of Registrant as Specified in Charter)
Nevada
001-36338
98-0468420
(State
or Other Jurisdiction
of Incorporation)
(Commission
File Number)
(I.R.S.
Employer
Identification No.)
321
Farmington Road, Mocksville, North Carolina
(Address
of Principal Executive Office)
27028
(Zip
Code)
Registrant’s
telephone number, including area code: (336) 940-3769
Check
the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under
any of the following provisions:
☐
Written
communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
☐
Soliciting
material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
☐
Pre-commencement
communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
☐
Pre-commencement
communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))
Securities
registered pursuant to Section 12(b) of the Act:
Title
of each class
Trading
symbol
Name
of each exchange on which registered
Common
Stock, $0.00001 par value
XXII
NASDAQ
Capital Market
Indicate
by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405
of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter). Emerging growth company ☐
If
an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying
with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐
Explanatory Note
This Amendment
No. 1 to the Current Report on Form 8-K (this “Amendment”) amends the Current Report on Form 8-K filed by 22nd Century Group,
Inc. (the “Company”) with the Securities and Exchange Commission on June 9, 2026 (the “Original Report”). This
Amendment is being filed solely to correct the exercise price of the Inducement Warrants disclosed in Item 1.01 of the Original Report
from $0.4626 to $3.57. Except as expressly set forth in this Amendment, all other information set forth in the Original Report remains
unchanged and is incorporated herein by reference.
Item 1.01 Entry into a Material Definitive Agreement.
Warrant
Inducement
On
June 8, 2026, the Company commenced a warrant inducement offering (the “Warrant Inducement”) with the holders
of certain outstanding warrants to purchase up to an aggregate of 5,345,591 shares of common stock (collectively, the “Existing
Warrants”), which Existing Warrants are exercisable at an exercise price of $3.57. The Company offered the holders of the Existing
Warrants an inducement period whereby the Company agreed to issue new warrants (the “Inducement Warrants”) to purchase
up to a number of shares of common stock equal to 100% of the number of shares of common stock issued pursuant to the exercise by the
holders of the Existing Warrants, for cash, at a reduced exercise price equal to $0.4626. Each holder agreed to exercise all of their
Existing Warrants immediately.
The
Inducement Warrants will be issued on substantially the same terms as the Existing Warrants, except that the Inducement Warrants will
be exercisable at any time on or after the Company’s stockholders approve the issuance of the Inducement Warrants and the shares
of common stock upon the exercise thereof (the “Stockholder Approval Date”), have an expiration date of five years
from the Stockholder Approval Date and have an exercise price equal to $3.57. The exercise price of the Inducement Warrants will
be subject to appropriate adjustment in the event of recapitalization events, stock dividends, stock splits, stock combinations, reclassifications,
reorganizations or similar events affecting the Company’s common stock. In addition, the Inducement Warrants will contain anti-dilution
protection provisions relating to a subsequent reverse stock splits and subsequent equity sales of shares of the Company’s common
stock or common stock equivalents at an effective price per share lower than the then effective exercise price of such Inducement Warrants
and will also adjust in the event of a reverse stock split. The Company also agreed to hold a meeting of stockholders to approve the
issuance of the shares of common stock underlying the Inducement Warrants pursuant to applicable Nasdaq rules.
The
Inducement Warrants will be issued in reliance upon an exemption from registration pursuant to Section 4(a)(2) under the Securities Act
of 1933, as amended (the “Securities Act”). The Company has agreed to, as soon as reasonably practicable, but in any
event no later than June 30, 2026, file a registration statement covering the resale of the shares of the Company’s common stock
issued or issuable upon the exercise of the Inducement Warrants. The Company shall use commercially reasonable efforts to cause such
registration statement to become effective within 45 days (the date such registration statement is declared effective, the “Effectiveness
Date”). The shares of common stock issuable under the Existing Warrants were previously registered
on Form S-3.
Subject
to limited exceptions, a holder of Inducement Warrants will not have the right to exercise any portion of its Inducement Warrants if
the holder (together with such holder’s affiliates, and any persons acting as a group together with such holder or any of such
holder’s affiliates) would beneficially own a number of shares of common stock in excess of 4.99% (or, upon election by a holder
prior to the issuance of any Inducement Warrants, 9.99%) of the shares of common stock then outstanding. At the holder’s option,
upon notice to the Company, the holder may increase or decrease this beneficial ownership limitation not to exceed 9.99% of the shares
of common stock then outstanding, with any such increase becoming effective upon 61 days’ prior notice to the Company.
The
Company agreed that, subject to certain exceptions, until 30 days after the later of the date that all of the shares issuable upon exercise
of the Inducement Warrants (the “Warrant Effectiveness Date”), and the date of Stockholder Approval Date, neither
the Company nor any of its subsidiaries will issue, enter into any agreement to issue or announce the issuance or proposed issuance of
any shares of common stock or common stock equivalents.
Each
holder participating in the Warrant Inducement shall have the option to elect, in the holder’s sole discretion, to direct that
all or a portion of the aggregate proceeds received by the Company from such holder’s exercise of the Existing Warrants hereunder
be applied by the Company to redeem shares of the Company’s Series B Convertible Preferred Stock (the “Series B Preferred
Stock”) held by such holder, at a redemption price equal to the par value of such shares of Series B Preferred Stock (the “Series
B Redemption”).
The
Company received aggregate gross cash proceeds of approximately $462,800 and redemption of $2,010,000, or 2,010 shares
of Series B Preferred Stock from the exercise of the Existing Warrants. The Company has 8,050 shares of Series B Preferred Stock
remaining.
Dawson
James Securities, Inc. (the “Placement Agent”) acted as the Company’s exclusive placement agent in connection
with the Warrant Inducement and the Company has agreed to pay the Placement Agent a cash fee equal to six percent (6.0%) of the aggregate
gross proceeds raised in the Warrant Inducement, an additional six percent (6.0%) cash fee of any cash exercise of the Inducement Warrants.
The
foregoing summaries of the Inducement Warrants and the inducement letters do not purport to be complete and are subject to, and qualified
in their entirety by, such documents attached as Exhibits 4.1 and 10.1, respectively, to this Current Report, which are incorporated
herein by reference.
Item
3.02 Unregistered Sales of Equity Securities
The
disclosure required by this Item, and included in Item 1.01 of this Current Report, is incorporated herein by reference. Neither the
Inducement Warrants nor the shares of the Company’s common stock issuable upon exercise of the Inducement Warrants have been registered
under the Securities Act, and may not be sold in the United States absent registration or an applicable exemption from the registration
requirements of the Securities Act.
Item 3.03. Material Modification to Rights of Security Holders.
On
June 10, 2026, the Company will fill a Certificate of Amendment (the “Certificate”) pursuant to Nevada Revised
Statutes (“NRS”) Section 78.209 with the Secretary of State of the State of Nevada authorizing a 1-for-20 reverse
stock split of the Company’s issued and outstanding shares of common stock (the “Reverse Stock Split”).
Reason
for the Reverse Stock Split
The
Reverse Stock Split was effected solely to enable the Company to expeditiously restore compliance with the continued listing standard
of NASDAQ Capital Market (“NASDAQ”).
Effects
of the Reverse Stock Split
Effective
Date; Symbol; CUSIP Number. The Reverse Stock Split will become effective at 12:01 a.m. Eastern Time on June 12, 2026, and will
be reflected with NASDAQ and in the marketplace at the open of business on June 12, 2026 (the “Effective Date”), whereupon
the shares of common stock will begin trading on a split-adjusted basis. In connection with the Reverse Stock Split, the Company’s
shares of common stock will continue to trade on NASDAQ under the symbol “XXII” but will trade under a new CUSIP Number,
90137F707.
Split
Adjustment; No Fractional Shares. On the Effective Date, the total number of shares of the Company’s common stock held
by each stockholder will be converted automatically into the number of whole shares of common stock equal to (i) the number of issued
and outstanding shares of common stock held by such stockholder immediately prior to the Reverse Stock Split, divided by (ii) 20.
No
fractional shares will be issued, and no cash or other consideration will be paid. Instead, the Company will issue one whole share of
the post-Reverse Stock Split common stock to any stockholder who otherwise would have received a fractional share as a result of the
Reverse Stock Split.
Non-Certificated
Shares; Certificated Shares. Stockholders who are holding their shares in electronic form at brokerage firms do not have to take
any action as the effect of the Reverse Stock Split will automatically be reflected in their brokerage accounts.
Stockholders
holding paper certificates may (but are not required to) send the certificates to the Company’s transfer agent at the address given
below. The transfer agent will issue a new share certificate reflecting the terms of the Reverse Stock Split to each requesting stockholder.
Continental
Stock Transfer & Trust Company
ONE
STATE STREET, 30th Floor
New
York, New York 10004
Phone:
(917) 262-2378
Please
contact Continental Stock Transfer & Trust Company for further information, related costs and procedures before sending any certificates.
State
Filing. The Reverse Stock Split was effected by the Company filing the Certificate pursuant to NRS Section 78.209 with
the Secretary of State of the State of Nevada on June 10, 2026. The Certificate will not be effective until the Effective Date. A copy
of the Certificate is attached hereto as Exhibit 3.1 and incorporated herein by reference.
Stockholder
Approval Required. Under Nevada law, because the Reverse Stock Split did not proportionately reduce the authorized shares, Stockholder
approval was required in accordance with NRS 78.2055. Under NRS 78.2055, “a corporation that desires to decrease the number of
issued and outstanding shares of a class or series held by each stockholder of record at the effective date and time of the change without
correspondingly decreasing the number of authorized shares of the same class or series may do so if: (a) The board of directors adopts
a resolution setting forth the proposal to decrease the number of issued and outstanding shares of a class or series; and, (b)
The proposal is approved by the vote of stockholders holding a majority of the voting power of the affected class or series, or such
greater proportion as may be provided in the articles of incorporation, regardless of limitations or restriction on the voting power
of the affected class or series.” As described herein, the Reverse Stock Split complies with such requirements.
Capitalization.
Prior to the Effective Date of the Certificate, the Company was authorized to issue 500,000,000 shares of common stock. As a result of
the Reverse Stock Split, the Company will remain authorized to issue 500,000,000 shares of common. As of June 9, 2026 (immediately
prior to the Effective Date), there were 10,326,551 shares of common stock outstanding (including 3,424,094 shares held in abeyance).
As a result of the Reverse Stock Split, there will be approximately 516,328 shares of common stock outstanding (including 171,205
shares held in abeyance, and subject to adjustment due to the effect of rounding fractional shares into whole shares). The Reverse
Stock Split will not have any effect on the stated par value of the common stock.
Each
stockholder’s percentage ownership interest in the Company and proportional voting power remains virtually unchanged as a result
of the Reverse Stock Split, except for minor changes and adjustments that will result from rounding fractional shares into whole shares.
All
options, warrants and shares of Series B Preferred Stock underlying shares of common stock of the Company outstanding immediately
prior to the Reverse Stock Split will be appropriately adjusted as a result of the Reverse Stock Split.
Item 5.03. Amendments to Articles of Incorporation or Bylaws.
The
information required by this Item 5.03 is set forth in Item 3.03 above, which information is incorporated herein by reference.
Item
9.01(d): Financial Statements and Exhibits.
Exhibit
3.1
Certificate of Amendment to Restated Articles of Incorporation
Exhibit
4.1
Form of Inducement Warrant
Exhibit
10.1
Form of Inducement Letter
Exhibit
104
Cover
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SIGNATURES
Pursuant
to the requirements of the Securities Exchange Act of 1934, the Registrant has duly caused this report to be signed on its behalf by
the undersigned hereunto duly authorized.
22nd
Century Group, Inc.
/s/
Lawrence D. Firestone
Date:
June 9, 2026
Lawrence
D. Firestone
Chief
Executive Officer
EX-3.1
EX-3.1
Filename: ex3-1.htm · Sequence: 2
Exhibit
3.1
CERTIFICATE
OF AMENDMENT
(Reverse
Split)
Pursuant
to the requirements of NRS 78.2055, the board of directors of 22nd Century Group, Inc. (the “Corporation”) proposed and recommended
to the stockholders a recommendation to decrease, on a 1-or-20 basis, the number of issued and outstanding shares of Common Stock, $0.00001
par value per share, of the Corporation, without any adjustment to the par value per share and without any reduction in the authorized
number of shares of Common Stock, and the proposal was approved by the stockholders holding shares in the Corporation entitling them
to exercise at least a majority of the voting power, or such greater proportion of the voting power as may be required in the case of
a vote by classes or series, or as is otherwise required by the provisions of the Articles of Incorporation.
ARTICLE
IV
CAPITAL STOCK
The
Restated Articles of Incorporation are hereby amended by adding the following as a new paragraph to the end of section 4.1:
“At
12:01 a.m. on June 12, 2026 (the “Effective Time”), each 20 shares of the Corporation’s Common Stock issued and outstanding
immediately prior to the Effective Time shall be reclassified and combined into one (1) validly issued, fully paid and non-assessable
share of the Corporation’s Common Stock automatically and without any further action by the Corporation or the holder thereof,
subject to the treatment of fractional share interests as described below (the “Reverse Stock Split”). The Corporation shall
not issue to any holder a fractional share of Common Stock on account of the Reverse Stock Split. Rather, any fractional share of Common
Stock resulting from such change shall be rounded upward to the nearest whole share of Common Stock. Share interests issued due to rounding
are given solely to save the expense and inconvenience of issuing fractional shares of Common Stock and do not represent separately bargained
for consideration. Until surrendered, each certificate that immediately prior to the Effective Time represented shares of Common Stock
(“Old Certificates”) shall only represent the number of whole shares of Common Stock into which the shares of Common Stock
formerly represented by such Old Certificate were combined into as a result of the Reverse Stock Split.”
EX-4.1
EX-4.1
Filename: ex4-1.htm · Sequence: 3
Exhibit
4.1
NEITHER
THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION
OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED
(THE “SECURITIES ACT”), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT
UNDER THE SECURITIES ACT OR PURSUANT TO AN AVAILABLE EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS
OF THE SECURITIES ACT AND IN ACCORDANCE WITH APPLICABLE STATE SECURITIES LAWS. THIS SECURITY AND THE SECURITIES ISSUABLE UPON EXERCISE
OF THIS SECURITY MAY BE PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN ACCOUNT OR OTHER LOAN SECURED BY SUCH SECURITIES.
COMMON
STOCK PURCHASE WARRANT
22ND
CENTURY GROUP, inc.
Warrant Shares: [_______] Issue Date:
[ ], 2026
THIS
COMMON STOCK PURCHASE WARRANT (the “Warrant”) certifies that, for value received, _____________ or its assigns (the
“Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set
forth, at any time on or after the Stockholder Approval Date (as defined below) (the “Initial Exercise Date”) and
on or prior to 5:00 p.m. (New York City time) on the date that is the five (5) year anniversary of the Stockholder Approval Date (the
“Termination Date”) but not thereafter, to subscribe for and purchase from 22nd Century Group, Inc., a Nevada corporation
(the “Company”), up to [______] shares (as subject to adjustment hereunder, the “Warrant Shares”)
of Common Stock. The purchase price of one share of Common Stock under this Warrant shall be equal to the Exercise Price, as defined
in Section 2(b).
Section
1. Definitions. In addition to the terms defined in the Letter Agreement (as defined below) and elsewhere in this Warrant,
the following terms have the meanings indicated in this Section 1:
“Affiliate”
means any Person that, directly or indirectly through one or more intermediaries, controls or is controlled by or is under common control
with a Person as such terms are used in and construed under Rule 405 under the Securities Act.
1
“Bid
Price” means, for any date, the price determined by the first of the following clauses that applies: (a) if the Common Stock
is then listed or quoted on a Trading Market, the bid price of the Common Stock for the time in question (or the nearest preceding date)
on the Trading Market on which the Common Stock is then listed or quoted as reported by Bloomberg (based on a Trading Day from 9:30 a.m.
(New York City time) to 4:02 p.m. (New York City time)), (b) if OTCQB or OTCQX is not a Trading Market, the volume weighted average price
of the Common Stock for such date (or the nearest preceding date) on OTCQB or OTCQX as applicable, (c) if the Common Stock is not then
listed or quoted for trading on OTCQB or OTCQX and if prices for the Common Stock are then reported on The Pink Open Market (or a similar
organization or agency succeeding to its functions of reporting prices), the most recent bid price per share of the Common Stock so reported,
or (d) in all other cases, the fair market value of a share of Common Stock as determined by an independent appraiser selected in good
faith by the Holders of a majority in interest of the Warrants then outstanding and reasonably acceptable to the Company, the fees and
expenses of which shall be paid by the Company.
“Board
of Directors” means the board of directors of the Company.
“Business
Day” means any day other than Saturday, Sunday or other day on which commercial banks in The City of New York are authorized
or required by law to remain closed; provided, however, for clarification, commercial banks shall not be deemed to be authorized
or required by law to remain closed due to “stay at home”, “shelter-in-place”, “non-essential employee”
or any other similar orders or restrictions or the closure of any physical branch locations at the direction of any governmental authority
so long as the electronic funds transfer systems (including for wire transfers) of commercial banks in The City of New York are generally
open for use by customers on such day.
“Commission”
means the United States Securities and Exchange Commission.
“Common
Stock” means the common stock of the Company, par value $0.00001 per share, and any other class of securities into which such
securities may hereafter be reclassified or changed.
“Common
Stock Equivalents” means any securities of the Company or the Subsidiaries which would entitle the holder thereof to acquire
at any time Common Stock, including, without limitation, any debt, preferred stock, right, option, warrant or other instrument that is
at any time convertible into or exercisable or exchangeable for, or otherwise entitles the holder thereof to receive, Common Stock.
“Exchange
Act” means the Securities Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder.
2
“Exempt
Issuance” means the issuance of (a) shares of Common Stock or options to employees, officers, directors or consultants of the
Company pursuant to any stock or option plan duly adopted for such purpose, by a majority of the non-employee members of the Board of
Directors or a majority of the members of a committee of non-employee directors established for such purpose for services rendered to
the Company, (b) securities upon the exercise or exchange of or conversion of any Warrants and/or other securities exercisable or exchangeable
for or convertible into shares of Common Stock issued and outstanding on the date of the Letter Agreement, provided that such securities
have not been amended since the date of the Letter Agreement to increase the number of such securities or to decrease the exercise price,
exchange price or conversion price of such securities (other than in connection with stock splits or combinations) or to extend the term
of such securities, (c) securities issued pursuant to acquisitions or strategic transactions approved by a majority of the disinterested
directors of the Company, provided that such securities are issued as “restricted securities” (as defined in Rule 144), and
provided that any such issuance shall only be to a Person (or to the equity holders of a Person) which is, itself or through its subsidiaries,
believed by the Company to be an operating company or an owner of an asset in a business synergistic with the business of the Company
and shall provide to the Company additional benefits in addition to the investment of funds, but shall not include a transaction in which
the Company is issuing securities primarily for the purpose of raising capital or to an entity whose primary business is investing in
securities and (d) securities issued to the Company’s existing lenders in exchange for the reduction of such debt.
“Letter
Agreement” means that certain letter agreement between the initial Holder hereof and the Company, dated as of June___, 2026,
pursuant to which such initial Holder agreed to exercise one or more warrants to purchase shares of Common Stock and the Company agreed
to issue to the initial Holder this Warrant.
“Person”
means an individual or corporation, partnership, trust, incorporated or unincorporated association, joint venture, limited liability
company, joint stock company, government (or an agency or subdivision thereof) or other entity of any kind.
“Rule
144” means Rule 144 promulgated by the Commission pursuant to the Securities Act, as such Rule may be amended or interpreted
from time to time, or any similar rule or regulation hereafter adopted by the Commission having substantially the same purpose and effect
as such Rule.
“Securities
Act” means the Securities Act of 1933, as amended, and the rules and regulations promulgated thereunder.
“Stockholder
Approval” means such approval as may be required by the applicable rules and regulations of the Nasdaq Capital Market (or any
successor entity) from the stockholders of the Company with respect to the issuance of Warrants in connection with the Letter Agreement
and the Warrant Shares upon the exercise thereof.
“Stockholder
Approval Date” means the date on which Stockholder Approval is received and deemed effective under Nevada law.
“Subsidiary”
means any significant subsidiary (as defined under Regulation S-X) of the Company as set forth in the Company’s filings with the
Commission, and shall, where applicable, also include any direct or indirect significant subsidiary of the Company formed or acquired
after the date hereof.
3
“Trading
Day” means a day on which the principal Trading Market is open for trading.
“Trading
Market” means any of the following markets or exchanges on which the Common Stock is listed or quoted for trading on the date
in question: the NYSE American, the Nasdaq Capital Market, the Nasdaq Global Market, the Nasdaq Global Select Market or the New York
Stock Exchange (or any successors to any of the foregoing).
“Transfer
Agent” means Continental Stock Transfer & Trust Company, the current transfer agent of the Company, with a mailing address
of 17 Battery Place, 8th Floor, New York, NY 10004, and any successor transfer agent of the Company.
“Variable
Rate Transaction” means a transaction in which the Company (i) issues or sells any debt or equity securities that are convertible
into, exchangeable or exercisable for, or include the right to receive additional shares of Common Stock either (A) at a conversion price,
exercise price or exchange rate or other price that is based upon and/or varies with the trading prices of or quotations for the shares
of Common Stock at any time after the initial issuance of such debt or equity securities, or (B) with a conversion, exercise or exchange
price that is subject to being reset at some future date after the initial issuance of such debt or equity security or upon the occurrence
of specified or contingent events directly or indirectly related to the business of the Company or the market for the Common Stock or
(ii) enters into, or effects a transaction under, any agreement, including, but not limited to, an equity line of credit or an “at-the-market
offering”, whereby the Company may issue securities at a future determined price regardless of whether shares pursuant to such
agreement have actually been issued and regardless of whether such agreement is subsequently canceled.
“VWAP”
means, for any date, the price determined by the first of the following clauses that applies: (a) if the Common Stock is then listed
or quoted on a Trading Market, the daily volume weighted average price of the Common Stock for such date (or the nearest preceding date)
on the Trading Market on which the Common Stock is then listed or quoted as reported by Bloomberg (based on a Trading Day from 9:30 a.m.
(New York City time) to 4:02 p.m. (New York City time)), (b) if the OTCQB Venture Market (“OTCQB”) or the OTCQX Best
Market (“OTCQX”) is not a Trading Market, the volume weighted average price of the Common Stock for such date (or
the nearest preceding date) on OTCQB or OTCQX as applicable, (c) if the Common Stock is not then listed or quoted for trading on OTCQB
or OTCQX and if prices for the Common Stock are then reported on the Pink Open Market (“Pink Market”) operated by
the OTC Markets, Inc. (or a similar organization or agency succeeding to its functions of reporting prices), the most recent bid price
per share of the Common Stock so reported, or (d) in all other cases, the fair market value of a share of Common Stock as determined
by an independent appraiser selected in good faith by the Holders of a majority in interest of the Warrants then outstanding and reasonably
acceptable to the Company, the fees and expenses of which shall be paid by the Company.
4
Section
2. Exercise.
a)
Exercise of Warrant. Exercise of the purchase rights represented by this Warrant may be made, in whole or in part, at any time
or times on or after the Initial Exercise Date and on or before the Termination Date by delivery to the Company of a duly executed PDF
copy submitted by e-mail (or e-mail attachment) of the Notice of Exercise in the form annexed hereto (the “Notice of Exercise”).
Within the earlier of (i) one (1) Trading Day and (ii) the number of Trading Days comprising the Standard Settlement Period (as defined
in Section 2(d)(i) herein) following the date of exercise as aforesaid, the Holder shall deliver the aggregate Exercise Price for the
Warrant Shares specified in the applicable Notice of Exercise by wire transfer or cashier’s check drawn on a United States bank
unless the cashless exercise procedure specified in Section 2(c) below is specified in the applicable Notice of Exercise. No ink-original
Notice of Exercise shall be required, nor shall any medallion guarantee (or other type of guarantee or notarization) of any Notice of
Exercise be required. Notwithstanding anything herein to the contrary, the Holder shall not be required to physically surrender this
Warrant to the Company until the Holder has purchased all of the Warrant Shares available hereunder and the Warrant has been exercised
in full, in which case, the Holder shall surrender this Warrant to the Company for cancellation within five (5) Trading Days of the date
on which the final Notice of Exercise is delivered to the Company. Partial exercises of this Warrant resulting in purchases of a portion
of the total number of Warrant Shares available hereunder shall have the effect of lowering the outstanding number of Warrant Shares
purchasable hereunder in an amount equal to the applicable number of Warrant Shares purchased. The Holder and the Company shall maintain
records showing the number of Warrant Shares purchased and the date of such purchases. The Company shall deliver any objection to any
Notice of Exercise within one (1) Business Day of receipt of such notice. The Holder and any assignee, by acceptance of this Warrant,
acknowledge and agree that, by reason of the provisions of this paragraph, following the purchase of a portion of the Warrant Shares
hereunder, the number of Warrant Shares available for purchase hereunder at any given time may be less than the amount stated on the
face hereof.
b)
Exercise Price. The exercise price per share of Common Stock under this Warrant shall be $[ ], subject to adjustment
hereunder (the “Exercise Price”).
5
c)
Cashless Exercise. If at the time of exercise hereof there is no effective registration statement registering the issuance of
the Warrant Shares, or the prospectus contained therein is not available for the resale of the Warrant Shares by the Holder, then this
Warrant may also be exercised, in whole or in part, at such time by means of a “cashless exercise” in which the Holder shall
be entitled to receive a number of Warrant Shares equal to the quotient obtained by dividing [(A-B) (X)] by (A), where:
(A) = as
applicable: (i) the VWAP on the Trading Day immediately preceding the date of the applicable
Notice of Exercise if such Notice of Exercise is (1) both executed and delivered pursuant
to Section 2(a) hereof on a day that is not a Trading Day or (2) both executed and delivered
pursuant to Section 2(a) hereof on a Trading Day prior to the opening of “regular trading
hours” (as defined in Rule 600(b) of Regulation NMS promulgated under the federal securities
laws) on such Trading Day, (ii) at the option of the Holder, either (y) the VWAP on the Trading
Day immediately preceding the date of the applicable Notice of Exercise or (z) the Bid Price
of the Common Stock on the principal Trading Market as reported by Bloomberg L.P. (“Bloomberg”)
as of the time of the Holder’s execution of the applicable Notice of Exercise if such
Notice of Exercise is executed during “regular trading hours” on a Trading Day
and is delivered within two (2) hours thereafter (including until two (2) hours after the
close of “regular trading hours” on a Trading Day) pursuant to Section 2(a) hereof
or (iii) the VWAP on the date of the applicable Notice of Exercise if the date of such Notice
of Exercise is a Trading Day and such Notice of Exercise is both executed and delivered pursuant
to Section 2(a) hereof after the close of “regular trading hours” on such Trading
Day;
(B) = the
Exercise Price of this Warrant, as adjusted hereunder; and
(X) = the
number of Warrant Shares that would be issuable upon exercise of this Warrant in accordance
with the terms of this Warrant if such exercise were by means of a cash exercise rather than
a cashless exercise.
If
Warrant Shares are issued in such a cashless exercise, the parties acknowledge and agree that in accordance with Section 3(a)(9) of the
Securities Act, the Warrant Shares shall take on the characteristics of the Warrants being exercised, and the holding period of the Warrant
Shares being issued may be tacked on to the holding period of this Warrant. The Company agrees not to take any position contrary to this
Section 2(c).
6
d)
Mechanics of Exercise.
i.
Delivery of Warrant Shares Upon Exercise. The Company shall cause the Warrant Shares purchased hereunder to be transmitted by
the Transfer Agent to the Holder by crediting the account of the Holder’s or its designee’s balance account with The Depository
Trust Company through its Deposit or Withdrawal at Custodian system (“DWAC”) if the Company is then a participant
in such system and either (A) there is an effective registration statement permitting the issuance of the Warrant Shares to or resale
of the Warrant Shares by Holder or (B) the Warrant Shares are eligible for resale by the Holder without volume and manner-of-sale limitations
pursuant to Rule 144 (assuming cashless exercise of the Warrants), and otherwise by physical delivery of a certificate, registered in
the Company’s share register in the name of the Holder or its designee, for the number of Warrant Shares to which the Holder is
entitled pursuant to such exercise to the address specified by the Holder in the Notice of Exercise by the date that is the earlier of
(i) one (1) Trading Day after delivery of the aggregate Exercise Price to the Company and (ii) the number of Trading Days comprising
the Standard Settlement Period after the delivery to the Company of the Notice of Exercise (such date, the “Warrant Share Delivery
Date”). Upon delivery of the Notice of Exercise, the Holder shall be deemed for all corporate purposes to have become the holder
of record of the Warrant Shares with respect to which this Warrant has been exercised, irrespective of the date of delivery of the Warrant
Shares, provided that payment of the aggregate Exercise Price (other than in the case of a cashless exercise) is received within the
earlier of (i) one (1) Trading Day and (ii) the number of Trading Days comprising the Standard Settlement Period following delivery of
the Notice of Exercise. If the Company fails for any reason to deliver to the Holder the Warrant Shares subject to a Notice of Exercise
by the Warrant Share Delivery Date, the Company shall pay to the Holder, in cash, as liquidated damages and not as a penalty, for each
$1,000 of Warrant Shares subject to such exercise (based on the VWAP of the Common Stock on the date of the applicable Notice of Exercise),
$10 per Trading Day (increasing to $20 per Trading Day on the third Trading Day after the Warrant Share Delivery Date) for each Trading
Day after such Warrant Share Delivery Date until such Warrant Shares are delivered or Holder rescinds such exercise. The Company agrees
to maintain a transfer agent that is a participant in the FAST program so long as this Warrant remains outstanding and exercisable. As
used herein, “Standard Settlement Period” means the standard settlement period, expressed in a number of Trading Days,
on the Company’s primary Trading Market with respect to the Common Stock as in effect on the date of delivery of the Notice of
Exercise. Notwithstanding the foregoing, with respect to any Notice(s) of Exercise delivered on or prior to 12:00 p.m. (New York City
time) on the Initial Exercise Date, which may be delivered at any time after the time of execution of the Purchase Agreement, the Company
agrees to deliver the Warrant Shares subject to such notice(s) by 4:00 p.m. (New York City time) on the Initial Exercise Date and the
Initial Exercise Date shall be the Warrant Share Delivery Date for purposes hereunder, provided that payment of the aggregate Exercise
Price (other than in the case of a cashless exercise) is received by such Warrant Share Delivery Date.
ii.
Delivery of New Warrants Upon Exercise. If this Warrant shall have been exercised in part, the Company shall, at the request of
a Holder and upon surrender of this Warrant certificate, at the time of delivery of the Warrant Shares, deliver to the Holder a new Warrant
evidencing the rights of the Holder to purchase the unpurchased Warrant Shares called for by this Warrant, which new Warrant shall in
all other respects be identical with this Warrant.
7
iii.
Rescission Rights. If the Company fails to cause the Transfer Agent to transmit to the Holder the Warrant Shares pursuant to Section
2(d)(i) by the Warrant Share Delivery Date, then the Holder will have the right to rescind such exercise.
iv.
Compensation for Buy-In on Failure to Timely Deliver Warrant Shares Upon Exercise. In addition to any other rights available to
the Holder, if the Company fails to cause the Transfer Agent to transmit to the Holder the Warrant Shares in accordance with the provisions
of Section 2(d)(i) above pursuant to an exercise on or before the Warrant Share Delivery Date, and if after such date the Holder is required
by its broker to purchase (in an open market transaction or otherwise) or the Holder’s brokerage firm otherwise purchases, shares
of Common Stock to deliver in satisfaction of a sale by the Holder of the Warrant Shares which the Holder anticipated receiving upon
such exercise (a “Buy-In”), then the Company shall (A) pay in cash to the Holder the amount, if any, by which (x)
the Holder’s total purchase price (including brokerage commissions, if any) for the shares of Common Stock so purchased exceeds
(y) the amount obtained by multiplying (1) the number of Warrant Shares that the Company was required to deliver to the Holder in connection
with the exercise at issue times (2) the price at which the sell order giving rise to such purchase obligation was executed, and (B)
at the option of the Holder, either reinstate the portion of the Warrant and equivalent number of Warrant Shares for which such exercise
was not honored (in which case such exercise shall be deemed rescinded) or deliver to the Holder the number of shares of Common Stock
that would have been issued had the Company timely complied with its exercise and delivery obligations hereunder. For example, if the
Holder purchases Common Stock having a total purchase price of $11,000 to cover a Buy-In with respect to an attempted exercise of shares
of Common Stock with an aggregate sale price giving rise to such purchase obligation of $10,000, under clause (A) of the immediately
preceding sentence the Company shall be required to pay the Holder $1,000. The Holder shall provide the Company written notice indicating
the amounts payable to the Holder in respect of the Buy-In and, upon request of the Company, evidence of the amount of such loss. Nothing
herein shall limit a Holder’s right to pursue any other remedies available to it hereunder, at law or in equity including, without
limitation, a decree of specific performance and/or injunctive relief with respect to the Company’s failure to timely deliver shares
of Common Stock upon exercise of the Warrant as required pursuant to the terms hereof.
v.
No Fractional Shares or Scrip. No fractional shares or scrip representing fractional shares shall be issued upon the exercise
of this Warrant. As to any fraction of a share which the Holder would otherwise be entitled to purchase upon such exercise, the Company
shall, at its election, either pay a cash adjustment in respect of such final fraction in an amount equal to such fraction multiplied
by the Exercise Price or round up to the next whole share.
vi.
Charges, Taxes and Expenses. Issuance of Warrant Shares shall be made without charge to the Holder for any issue or transfer tax
or other incidental expense in respect of the issuance of such Warrant Shares, all of which taxes and expenses shall be paid by the Company,
and such Warrant Shares shall be issued in the name of the Holder or in such name or names as may be directed by the Holder; provided,
however, that, in the event that Warrant Shares are to be issued in a name other than the name of the Holder, this Warrant when
surrendered for exercise shall be accompanied by the Assignment Form attached hereto duly executed by the Holder and the Company may
require, as a condition thereto, the payment of a sum sufficient to reimburse it for any transfer tax incidental thereto. The Company
shall pay all Transfer Agent fees required for same-day processing of any Notice of Exercise and all fees to the Depository Trust Company
(or another established clearing corporation performing similar functions) required for same-day electronic delivery of the Warrant Shares.
vii.
Closing of Books. The Company will not close its stockholder books or records in any manner which prevents the timely exercise
of this Warrant, pursuant to the terms hereof.
8
e)
Holder’s Exercise Limitations. The Company shall not effect any exercise of this Warrant, and a Holder shall not have the
right to exercise any portion of this Warrant, pursuant to Section 2 or otherwise, to the extent that after giving effect to such issuance
after exercise as set forth on the applicable Notice of Exercise, the Holder (together with the Holder’s Affiliates, and any other
Persons acting as a group together with the Holder or any of the Holder’s Affiliates (such Persons, “Attribution Parties”)),
would beneficially own in excess of the Beneficial Ownership Limitation (as defined below). For purposes of the foregoing sentence, the
number of shares of Common Stock beneficially owned by the Holder and its Affiliates and Attribution Parties shall include the number
of shares of Common Stock issuable upon exercise of this Warrant with respect to which such determination is being made, but shall exclude
the number of shares of Common Stock which would be issuable upon (i) exercise of the remaining, nonexercised portion of this Warrant
beneficially owned by the Holder or any of its Affiliates or Attribution Parties and (ii) exercise or conversion of the unexercised or
nonconverted portion of any other securities of the Company (including, without limitation, any other Common Stock Equivalents) subject
to a limitation on conversion or exercise analogous to the limitation contained herein beneficially owned by the Holder or any of its
Affiliates or Attribution Parties. Except as set forth in the preceding sentence, for purposes of this Section 2(e), beneficial ownership
shall be calculated in accordance with Section 13(d) of the Exchange Act and the rules and regulations promulgated thereunder, it being
acknowledged by the Holder that the Company is not representing to the Holder that such calculation is in compliance with Section 13(d)
of the Exchange Act and the Holder is solely responsible for any schedules required to be filed in accordance therewith. To the extent
that the limitation contained in this Section 2(e) applies, the determination of whether this Warrant is exercisable (in relation to
other securities owned by the Holder together with any Affiliates and Attribution Parties) and of which portion of this Warrant is exercisable
shall be in the sole discretion of the Holder, and the submission of a Notice of Exercise shall be deemed to be the Holder’s determination
of whether this Warrant is exercisable (in relation to other securities owned by the Holder together with any Affiliates and Attribution
Parties) and of which portion of this Warrant is exercisable, in each case subject to the Beneficial Ownership Limitation, and the Company
shall have no obligation to verify or confirm the accuracy of such determination. In addition, a determination as to any group status
as contemplated above shall be determined in accordance with Section 13(d) of the Exchange Act and the rules and regulations promulgated
thereunder. For purposes of this Section 2(e), in determining the number of outstanding shares of Common Stock, a Holder may rely on
the number of outstanding shares of Common Stock as reflected in (A) the Company’s most recent periodic or annual report filed
with the Commission, as the case may be, (B) a more recent public announcement by the Company or (C) a more recent written notice by
the Company or the Transfer Agent setting forth the number of shares of Common Stock outstanding. Upon the written or oral request of
a Holder, the Company shall within one Trading Day confirm orally and in writing to the Holder the number of shares of Common Stock then
outstanding. In any case, the number of outstanding shares of Common Stock shall be determined after giving effect to the conversion
or exercise of securities of the Company, including this Warrant, by the Holder or its Affiliates or Attribution Parties since the date
as of which such number of outstanding shares of Common Stock was reported. The “Beneficial Ownership Limitation”
shall be [9.99/4.99%] of the number of shares of the Common Stock outstanding immediately after giving effect to the issuance of shares
of Common Stock issuable upon exercise of this Warrant. The Holder, upon notice to the Company, may increase or decrease the Beneficial
Ownership Limitation provisions of this Section 2(e), provided that the Beneficial Ownership Limitation in no event exceeds 9.99% of
the number of shares of the Common Stock outstanding immediately after giving effect to the issuance of shares of Common Stock upon exercise
of this Warrant held by the Holder and the provisions of this Section 2(e) shall continue to apply. Any increase in the Beneficial Ownership
Limitation will not be effective until the 61st day after such notice is delivered to the Company. The provisions of this
paragraph shall be construed and implemented in a manner otherwise than in strict conformity with the terms of this Section 2(e) to correct
this paragraph (or any portion hereof) which may be defective or inconsistent with the intended Beneficial Ownership Limitation herein
contained or to make changes or supplements necessary or desirable to properly give effect to such limitation. The limitations contained
in this paragraph shall apply to a successor holder of this Warrant.
9
Section
3. Certain Adjustments.
a)
Stock Dividends and Splits. If the Company, at any time while this Warrant is outstanding: (i) pays a stock dividend or otherwise
makes a distribution or distributions on shares of its Common Stock or any other equity or equity equivalent securities payable in shares
of Common Stock (which, for avoidance of doubt, shall not include any shares of Common Stock issued by the Company upon exercise of this
Warrant), (ii) subdivides outstanding shares of Common Stock into a larger number of shares, (iii) combines (including by way of reverse
stock split) outstanding shares of Common Stock into a smaller number of shares, or (iv) issues by reclassification of shares of the
Common Stock any shares of capital stock of the Company, then in each case the Exercise Price shall be multiplied by a fraction of which
the numerator shall be the number of shares of Common Stock (excluding treasury shares, if any) outstanding immediately before such event
and of which the denominator shall be the number of shares of Common Stock outstanding immediately after such event, and the number of
shares issuable upon exercise of this Warrant shall be proportionately adjusted such that the aggregate Exercise Price of this Warrant
shall remain unchanged. Any adjustment made pursuant to this Section 3(a) shall become effective immediately after the record date for
the determination of stockholders entitled to receive such dividend or distribution and shall become effective immediately after the
effective date in the case of a subdivision, combination or re-classification.
b)
Subsequent Equity Sales. If the Company or any Subsidiary thereof, as applicable, at any time while this Warrant is outstanding,
shall sell, enter into an agreement to sell or grant any option to purchase, or sell or grant any right to reprice, or otherwise dispose
of or issue (or announce any offer, sale, grant or any option to purchase or other disposition) any Common Stock or Common Stock Equivalents,
at an effective price per share less than the Exercise Price then in effect (such lower price, the “Base Share Price”
and such issuances collectively, a “Dilutive Issuance”) (it being understood and agreed that if the holder of the
Common Stock or Common Stock Equivalents so issued shall at any time, whether by operation of purchase price adjustments, reset provisions,
floating conversion, exercise or exchange prices or otherwise, or due to warrants, options or rights per share which are issued in connection
with such issuance, be entitled to receive shares of Common Stock at an effective price per share that is less than the Exercise Price,
such issuance shall be deemed to have occurred for less than the Exercise Price on such date of the Dilutive Issuance at such effective
price), then simultaneously with the consummation (or, if earlier, the announcement) of each Dilutive Issuance the Exercise Price shall
be reduced and only reduced to equal the Base Share Price. Notwithstanding the foregoing, no adjustments shall be made, paid or issued
under this Section 3(b) in respect of an Exempt Issuance. The Company shall notify the Holder, in writing, no later than the Trading
Day following the issuance or deemed issuance of any Common Stock or Common Stock Equivalents subject to this Section 3(b), indicating
therein the applicable issuance price, or applicable reset price, exchange price, conversion price and other pricing terms (such notice,
the “Dilutive Issuance Notice”). For purposes of clarification, whether or not the Company provides a Dilutive Issuance
Notice pursuant to this Section 3(b), upon the occurrence of any Dilutive Issuance, the Holder is entitled to receive a number of Warrant
Shares, subject to the Company obtaining Stockholder Approval pursuant to the terms of the Letter Agreement, based upon the Base Share
Price regardless of whether the Holder accurately refers to the Base Share Price in the Notice of Exercise. If the Company enters into
a Variable Rate Transaction, the Company shall be deemed to have issued Common Stock or Common Stock Equivalents at the lowest possible
price, conversion price or exercise price at which such securities may be issued, converted or exercised provided; however that the foregoing
shall not apply to an “at-the-market” offering program or similar offering facility unless and until the Company actually
sells shares under such program at a price per share less than the Exercise Price then in effect.
10
c)
Subsequent Rights Offerings. In addition to any adjustments pursuant to Section 3(a) above, if at any time the Company grants,
issues or sells any Common Stock Equivalents or rights to purchase stock, warrants, securities or other property pro rata to the record
holders of any class of shares of Common Stock (the “Purchase Rights”), then the Holder will be entitled to acquire,
upon the terms applicable to such Purchase Rights, the aggregate Purchase Rights which the Holder could have acquired if the Holder had
held the number of shares of Common Stock acquirable upon complete exercise of this Warrant (without regard to any limitations on exercise
hereof, including without limitation, the Beneficial Ownership Limitation) immediately before the date on which a record is taken for
the grant, issuance or sale of such Purchase Rights, or, if no such record is taken, the date as of which the record holders of shares
of Common Stock are to be determined for the grant, issue or sale of such Purchase Rights (provided, however, that, to the extent that
the Holder’s right to participate in any such Purchase Right would result in the Holder exceeding the Beneficial Ownership Limitation,
then the Holder shall not be entitled to participate in such Purchase Right to such extent (or beneficial ownership of such shares of
Common Stock as a result of such Purchase Right to such extent) and such Purchase Right to such extent shall be held in abeyance for
the Holder until such time, if ever, as its right thereto would not result in the Holder exceeding the Beneficial Ownership Limitation).
d)
Pro Rata Distributions. During such time as this Warrant is outstanding, if the Company shall declare or make any dividend or
other distribution of its assets (or rights to acquire its assets) to holders of shares of Common Stock, by way of return of capital
or otherwise (including, without limitation, any distribution of cash, stock or other securities, property or options by way of a dividend,
spin off, reclassification, corporate rearrangement, scheme of arrangement or other similar transaction) (a “Distribution”),
at any time after the issuance of this Warrant, then, in each such case, the Holder shall be entitled to participate in such Distribution
to the same extent that the Holder would have participated therein if the Holder had held the number of shares of Common Stock acquirable
upon complete exercise of this Warrant (without regard to any limitations on exercise hereof, including without limitation, the Beneficial
Ownership Limitation) immediately before the date of which a record is taken for such Distribution, or, if no such record is taken, the
date as of which the record holders of shares of Common Stock are to be determined for the participation in such Distribution (provided,
however, that, to the extent that the Holder’s right to participate in any such Distribution would result in the Holder
exceeding the Beneficial Ownership Limitation, then the Holder shall not be entitled to participate in such Distribution to such extent
(or in the beneficial ownership of any shares of Common Stock as a result of such Distribution to such extent) and the portion of such
Distribution shall be held in abeyance for the benefit of the Holder until such time, if ever, as its right thereto would not result
in the Holder exceeding the Beneficial Ownership Limitation). To the extent that this Warrant has not been partially or completely exercised
at the time of such Distribution, such portion of the Distribution shall be held in abeyance for the benefit of the Holder until the
Holder has exercised this Warrant.
11
e)
Fundamental Transaction. If, at any time while this Warrant is outstanding, (i) the Company, directly or indirectly, in one or
more related transactions effects any merger or consolidation of the Company with or into another Person, (ii) the Company, directly
or indirectly, effects any sale, lease, license, assignment, transfer, conveyance or other disposition of all or substantially all of
its assets in one or a series of related transactions, (iii) any, direct or indirect, purchase offer, tender offer or exchange offer
(whether by the Company or another Person) is completed pursuant to which holders of Common Stock are permitted to sell, tender or exchange
their shares for other securities, cash or property and has been accepted by the holders of 50% or more of the outstanding Common Stock
or 50% or more of the voting power of the common equity of the Company, (iv) the Company, directly or indirectly, in one or more related
transactions effects any reclassification, reorganization or recapitalization of the Common Stock or any compulsory share exchange pursuant
to which the Common Stock is effectively converted into or exchanged for other securities, cash or property, or (v) the Company, directly
or indirectly, in one or more related transactions consummates a stock or share purchase agreement or other business combination (including,
without limitation, a reorganization, recapitalization, spin-off, merger or scheme of arrangement) with another Person or group of Persons
whereby such other Person or group acquires 50% or more of the outstanding shares of Common Stock or 50% or more of the voting power
of the common equity of the Company (each a “Fundamental Transaction”), then, upon any subsequent exercise of this
Warrant, the Holder shall have the right to receive, for each Warrant Share that would have been issuable upon such exercise immediately
prior to the occurrence of such Fundamental Transaction (without regard to any limitation in Section 2(e) on the exercise of this Warrant),
the same consideration (the “Alternate Consideration”) receivable as a result of such Fundamental Transaction by a
holder of the number of shares of Common Stock for which this Warrant is exercisable immediately prior to such Fundamental Transaction
(without regard to any limitation in Section 2(e) on the exercise of this Warrant). For purposes of any such exercise, the determination
of the Exercise Price shall be appropriately adjusted to apply to such Alternate Consideration based on the amount of Alternate Consideration
issuable in respect of one share of Common Stock in such Fundamental Transaction, and the Company shall apportion the Exercise Price
among the Alternate Consideration in a reasonable manner reflecting the relative value of any different components of the Alternate Consideration.
If holders of Common Stock are given any choice as to the securities, cash or property to be received in a Fundamental Transaction, then
the Holder shall be given the same choice as to the Alternate Consideration it receives upon any exercise of this Warrant following such
Fundamental Transaction. Notwithstanding anything to the contrary, in the event of a Fundamental Transaction, the Company or any Successor
Entity (as defined below) shall, at the Holder’s option, exercisable at any time concurrently with the consummation of the Fundamental
Transaction (or, if later, the date of the public announcement of the applicable Fundamental Transaction), purchase this Warrant from
the Holder by paying to the Holder an amount of cash equal to the Black Scholes Value (as defined below) of the remaining unexercised
portion of this Warrant on the date of the consummation of such Fundamental Transaction; provided, however, that, if the
Fundamental Transaction is not within the Company’s control, including not approved by the Company’s Board of Directors,
the Holder shall only be entitled to receive from the Company or any Successor Entity the same type or form of consideration (and in
the same proportion), at the Black Scholes Value of the unexercised portion of this Warrant, that is being offered and paid to the holders
of Common Stock of the Company in connection with the Fundamental Transaction, whether that consideration be in the form of cash, stock
or any combination thereof, or whether the holders of Common Stock are given the choice to receive from among alternative forms of consideration
in connection with the Fundamental Transaction; provided, further, that if holders of Common Stock of the Company are not
offered or paid any consideration in such Fundamental Transaction, such holders of Common Stock will be deemed to have received common
stock of the Successor Entity (which Entity may be the Company following such Fundamental Transaction) in such Fundamental Transaction.
“Black Scholes Value” means the value of this Warrant based on the Black-Scholes Option Pricing Model and inputs determined
by the Company’s Board of Directors acting reasonably and in good faith in conjunction with a reputable investment bank or financial
advisor. The payment of the Black Scholes Value will be made by wire transfer of immediately available funds (or such other consideration)
within the later of (i) five Business Days of the Holder’s election and (ii) the date of consummation of the Fundamental Transaction.
The Company shall cause any successor entity in a Fundamental Transaction in which the Company is not the survivor (the “Successor
Entity”) to assume in writing all of the obligations of the Company under this Warrant and the Letter Agreement in accordance
with the provisions of this Section 3(e) pursuant to written agreements in form and substance reasonably satisfactory to the Holder and
approved by the Holder (without unreasonable delay) prior to such Fundamental Transaction and shall, at the option of the Holder, deliver
to the Holder in exchange for this Warrant a security of the Successor Entity evidenced by a written instrument substantially similar
in form and substance to this Warrant which is exercisable for a corresponding number of shares of capital stock of such Successor Entity
(or its parent entity) equivalent to the shares of Common Stock acquirable and receivable upon exercise of this Warrant (without regard
to any limitations on the exercise of this Warrant) prior to such Fundamental Transaction, and with an exercise price which applies the
exercise price hereunder to such shares of capital stock (but taking into account the relative value of the shares of Common Stock pursuant
to such Fundamental Transaction and the value of such shares of capital stock, such number of shares of capital stock and such exercise
price being for the purpose of protecting the economic value of this Warrant immediately prior to the consummation of such Fundamental
Transaction), and which is reasonably satisfactory in form and substance to the Holder. Upon the occurrence of any such Fundamental Transaction,
the Successor Entity shall be added to the term “Company” under this Warrant (so that from and after the occurrence or consummation
of such Fundamental Transaction, each and every provision of this Warrant and the Letter Agreement referring to the “Company”
shall refer instead to each of the Company and the Successor Entity or Successor Entities, jointly and severally), and the Successor
Entity or Successor Entities, jointly and severally with the Company, may exercise every right and power of the Company prior thereto
and the Successor Entity or Successor Entities shall assume all of the obligations of the Company prior thereto under this Warrant and
the Letter Agreement with the same effect as if the Company and such Successor Entity or Successor Entities, jointly and severally, had
been named as the Company herein. For the avoidance of doubt, the Holder shall be entitled to the benefits of the provisions of this
Section 3(e) regardless of (i) whether the Company has sufficient authorized shares of Common Stock for the issuance of Warrant Shares
and/or (ii) whether a Fundamental Transaction occurs prior to the Initial Exercise Date.
12
f)
Share Combination Event Adjustment. In addition to the adjustments set forth in this Section 3, if at any time on or after the
Issue Date there occurs a reverse share split involving the shares of Common Stock (a “Share Combination Event”, and such
date thereof, the “Share Combination Event Date”) at the close of trading on the primary Trading Market on the day prior
to the Share Combination Event, the Exercise Price then in effect shall be reduced (but in no event increased) to the split adjusted
closing share price on such date subject to a floor price of $[ ]2 (as adjusted for the split) (“Event Market Price”)
and the number of Warrant Shares issuable upon exercise of this Warrant hereunder (such resulting number, the “Share Combination
Issuable Shares”) shall be increased such that the aggregate Exercise Price payable hereunder, after taking into account the decrease
in the Exercise Price, shall be equal to the aggregate Exercise Price on the Issuance Date for the Warrant Shares then outstanding, which
shall be subject to the Company obtaining Stockholder Approval pursuant to the terms of the Letter Agreement. Notwithstanding the foregoing,
the provisions of this Section 3(f) shall no longer be in effect and shall be considered null and void after the occurrence of one (1)
adjustment of the Exercise Price upon a Share Combination Event, pursuant to this Section 3(f).
g)
Calculations. All calculations under this Section 3 shall be made to the nearest cent or the nearest 1/100th of a share, as the
case may be. For purposes of this Section 3, the number of shares of Common Stock deemed to be issued and outstanding as of a given date
shall be the sum of the number of shares of Common Stock (excluding treasury shares, if any) issued and outstanding.
h)
Notice to Holder.
i.
Adjustment to Exercise Price. Whenever the Exercise Price is adjusted pursuant to any provision of this Section 3, the Company
shall promptly deliver to the Holder by email a notice setting forth the Exercise Price after such adjustment and any resulting adjustment
to the number of Warrant Shares and setting forth a brief statement of the facts requiring such adjustment.
2
To equal 20% of the Nasdaq minimum price.
13
ii.
Notice to Allow Exercise by Holder. If (A) the Company shall declare a dividend (or any other distribution in whatever form) on
the Common Stock, (B) the Company shall declare a special nonrecurring cash dividend on or a redemption of the Common Stock, (C) the
Company shall authorize the granting to all holders of the Common Stock rights or warrants to subscribe for or purchase any shares of
capital stock of any class or of any rights, (D) the approval of any stockholders of the Company shall be required in connection with
any reclassification of the Common Stock, any consolidation or merger to which the Company (or any of its Subsidiaries) is a party, any
sale or transfer of all or substantially all of its assets, or any compulsory share exchange whereby the Common Stock is converted into
other securities, cash or property, or (E) the Company shall authorize the voluntary or involuntary dissolution, liquidation or winding
up of the affairs of the Company, then, in each case, the Company shall cause to be delivered by email to the Holder at its last email
address as it shall appear upon the Warrant Register of the Company (unless such notice is filed with the Commission, which in such case,
no additional notice is required to be provided to the Holder), at least 10 calendar days prior to the applicable record or effective
date hereinafter specified, a notice stating (x) the date on which a record is to be taken for the purpose of such dividend, distribution,
redemption, rights or warrants, or if a record is not to be taken, the date as of which the holders of the Common Stock of record to
be entitled to such dividend, distributions, redemption, rights or warrants are to be determined or (y) the date on which such reclassification,
consolidation, merger, sale, transfer or share exchange is expected to become effective or close, and the date as of which it is expected
that holders of the Common Stock of record shall be entitled to exchange their shares of the Common Stock for securities, cash or other
property deliverable upon such reclassification, consolidation, merger, sale, transfer or share exchange; provided that the failure to
deliver such notice or any defect therein or in the delivery thereof shall not affect the validity of the corporate action required to
be specified in such notice. To the extent that any notice provided in this Warrant constitutes, or contains, material, non-public information
regarding the Company or any of the Subsidiaries, the Company shall simultaneously file such notice with the Commission pursuant to a
Current Report on Form 8-K. The Holder shall remain entitled to exercise this Warrant during the period commencing on the date of such
notice to the effective date of the event triggering such notice except as may otherwise be expressly set forth herein.
i)
Voluntary Adjustment By Company. Subject to the rules and regulations of the Trading Market, the Company may at any time during
the term of this Warrant reduce the then current Exercise Price to any amount and for any period of time deemed appropriate by the board
of directors of the Company.
14
Section
4. Transfer of Warrant.
a)
Transferability. Subject to compliance with any applicable securities laws and the conditions set forth in Section 4(d) hereof,
this Warrant and all rights hereunder (including, without limitation, any registration rights) are transferable, in whole or in part,
upon surrender of this Warrant at the principal office of the Company or its designated agent, together with a written assignment of
this Warrant substantially in the form attached hereto duly executed by the Holder or its agent or attorney and funds sufficient to pay
any transfer taxes payable upon the making of such transfer. Upon such surrender and, if required, such payment, the Company shall execute
and deliver a new Warrant or Warrants in the name of the assignee or assignees, as applicable, and in the denomination or denominations
specified in such instrument of assignment, and shall issue to the assignor a new Warrant evidencing the portion of this Warrant not
so assigned, and this Warrant shall promptly be cancelled. Notwithstanding anything herein to the contrary, the Holder shall not be required
to physically surrender this Warrant to the Company unless the Holder has assigned this Warrant in full, in which case, the Holder shall
surrender this Warrant to the Company within three (3) Trading Days of the date on which the Holder delivers an assignment form to the
Company assigning this Warrant in full. The Warrant, if properly assigned in accordance herewith, may be exercised by a new holder for
the purchase of Warrant Shares without having a new Warrant issued.
b)
New Warrants. This Warrant may be divided or combined with other Warrants upon presentation hereof at the aforesaid office of
the Company, together with a written notice specifying the names and denominations in which new Warrants are to be issued, signed by
the Holder or its agent or attorney. Subject to compliance with Section 4(a), as to any transfer which may be involved in such division
or combination, the Company shall execute and deliver a new Warrant or Warrants in exchange for the Warrant or Warrants to be divided
or combined in accordance with such notice. All Warrants issued on transfers or exchanges shall be dated the initial issuance date of
this Warrant and shall be identical with this Warrant except as to the number of Warrant Shares issuable pursuant thereto.
c)
Warrant Register. The Company shall register this Warrant, upon records to be maintained by the Company for that purpose (the
“Warrant Register”), in the name of the record Holder hereof from time to time. The Company may deem and treat the
registered Holder of this Warrant as the absolute owner hereof for the purpose of any exercise hereof or any distribution to the Holder,
and for all other purposes, absent actual notice to the contrary.
15
d)
Transfer Restrictions. If, at the time of the surrender of this Warrant in connection with any transfer of this Warrant, the transfer
of this Warrant shall not be either (i) registered pursuant to an effective registration statement under the Securities Act and under
applicable state securities or blue sky laws or (ii) eligible for resale without volume or manner-of-sale restrictions or current public
information requirements pursuant to Rule 144, the Company may require, as a condition of allowing such transfer, that the Holder or
transferee of this Warrant, as the case may be, provides to the Company an opinion of counsel in customary form to the effect that the
transfer of this Warrant does not require registration under the Securities Act.
e)
Representation by the Holder. The Holder, by the acceptance hereof, represents and warrants that it is acquiring this Warrant
and, upon any exercise hereof, will acquire the Warrant Shares issuable upon such exercise, for its own account and not with a view to
or for distributing or reselling such Warrant Shares or any part thereof in violation of the Securities Act or any applicable state securities
law, except pursuant to sales registered or exempted under the Securities Act.
Section
5. Miscellaneous.
a)
No Rights as Stockholder Until Exercise; No Settlement in Cash. This Warrant does not entitle the Holder to any voting rights,
dividends or other rights as a stockholder of the Company prior to the exercise hereof as set forth in Section 2(d)(i), except as expressly
set forth in Section 3. Without limiting any rights of a Holder to receive Warrant Shares on a “cashless exercise” pursuant
to Section 2(c) or to receive cash payments pursuant to Section 2(d)(i) and Section 2(d)(iv) herein, in no event shall the Company be
required to net cash settle an exercise of this Warrant.
b)
Loss, Theft, Destruction or Mutilation of Warrant. The Company covenants that upon receipt by the Company of evidence reasonably
satisfactory to it of the loss, theft, destruction or mutilation of this Warrant or any stock certificate relating to the Warrant Shares,
and in case of loss, theft or destruction, of indemnity or security reasonably satisfactory to it (which, in the case of the Warrant,
shall not include the posting of any bond), and upon surrender and cancellation of such Warrant or stock certificate, if mutilated, the
Company will make and deliver a new Warrant or stock certificate of like tenor and dated as of such cancellation, in lieu of such Warrant
or stock certificate.
c)
Saturdays, Sundays, Holidays, etc. If the last or appointed day for the taking of any action or the expiration of any right required
or granted herein shall not be a Business Day, then such action may be taken or such right may be exercised on the next succeeding Business
Day.
16
d)
Authorized Shares.
The
Company covenants that, during the period the Warrant is outstanding, it will reserve from its authorized and unissued Common Stock a
sufficient number of shares to provide for the issuance of the Warrant Shares upon the exercise of any purchase rights under this Warrant.
The Company further covenants that its issuance of this Warrant shall constitute full authority to its officers who are charged with
the duty of issuing the necessary Warrant Shares upon the exercise of the purchase rights under this Warrant. The Company will take all
such reasonable action as may be necessary to assure that such Warrant Shares may be issued as provided herein without violation of any
applicable law or regulation, or of any requirements of the Trading Market upon which the Common Stock may be listed. The Company covenants
that all Warrant Shares which may be issued upon the exercise of the purchase rights represented by this Warrant will, upon exercise
of the purchase rights represented by this Warrant and payment for such Warrant Shares in accordance herewith, be duly authorized, validly
issued, fully paid and nonassessable and free from all taxes, liens and charges created by the Company in respect of the issue thereof
(other than taxes in respect of any transfer occurring contemporaneously with such issue).
Except
and to the extent as waived or consented to by the Holder, the Company shall not by any action, including, without limitation, amending
its certificate of incorporation or through any reorganization, transfer of assets, consolidation, merger, dissolution, issue or sale
of securities or any other voluntary action, avoid or seek to avoid the observance or performance of any of the terms of this Warrant,
but will at all times in good faith assist in the carrying out of all such terms and in the taking of all such actions as may be necessary
or appropriate to protect the rights of Holder as set forth in this Warrant against impairment. Without limiting the generality of the
foregoing, the Company will (i) not increase the par value of any Warrant Shares above the amount payable therefor upon such exercise
immediately prior to such increase in par value, (ii) take all such action as may be necessary or appropriate in order that the Company
may validly and legally issue fully paid and nonassessable Warrant Shares upon the exercise of this Warrant and (iii) use commercially
reasonable efforts to obtain all such authorizations, exemptions or consents from any public regulatory body having jurisdiction thereof,
as may be, necessary to enable the Company to perform its obligations under this Warrant.
Before
taking any action which would result in an adjustment in the number of Warrant Shares for which this Warrant is exercisable or in the
Exercise Price, the Company shall obtain all such authorizations or exemptions thereof, or consents thereto, as may be necessary from
any public regulatory body or bodies having jurisdiction thereof.
17
e)
Governing Law. All questions concerning the construction, validity, enforcement and interpretation of this Warrant shall be governed
by and construed and enforced in accordance with the internal laws of the State of New York, without regard to the principles of conflicts
of law thereof. Each party agrees that all legal proceedings concerning the interpretations, enforcement and defense of the transactions
contemplated by this Warrant (whether brought against a party hereto or their respective affiliates, directors, officers, shareholders,
partners, members, employees or agents) shall be commenced exclusively in the state and federal courts sitting in the City of New York.
Each party hereby irrevocably submits to the exclusive jurisdiction of the state and federal courts sitting in the City of New York,
Borough of Manhattan for the adjudication of any dispute hereunder or in connection herewith or with any transaction contemplated hereby
or discussed herein, and hereby irrevocably waives, and agrees not to assert in any suit, action or proceeding, any claim that it is
not personally subject to the jurisdiction of any such court, that such suit, action or proceeding is improper or is an inconvenient
venue for such proceeding. Each party hereby irrevocably waives personal service of process and consents to process being served in any
such suit, action or proceeding by mailing a copy thereof via registered or certified mail or overnight delivery (with evidence of delivery)
to such party at the address in effect for notices to it under this Warrant and agrees that such service shall constitute good and sufficient
service of process and notice thereof. Nothing contained herein shall be deemed to limit in any way any right to serve process in any
other manner permitted by law. If either party shall commence an action, suit or proceeding to enforce any provisions of this Warrant,
the prevailing party in such action, suit or proceeding shall be reimbursed by the other party for their reasonable attorneys’
fees and other costs and expenses incurred with the investigation, preparation and prosecution of such action or proceeding.
f)
Restrictions. The Holder acknowledges that the Warrant Shares acquired upon the exercise of this Warrant, if not registered, and
the Holder does not utilize cashless exercise, will have restrictions upon resale imposed by state and federal securities laws.
g)
Nonwaiver and Expenses. No course of dealing or any delay or failure to exercise any right hereunder on the part of Holder shall
operate as a waiver of such right or otherwise prejudice the Holder’s rights, powers or remedies. Without limiting any other provision
of this Warrant, if the Company willfully and knowingly fails to comply with any provision of this Warrant, which results in any material
damages to the Holder, the Company shall pay to the Holder such amounts as shall be sufficient to cover any costs and expenses including,
but not limited to, reasonable attorneys’ fees, including those of appellate proceedings, incurred by the Holder in collecting
any amounts due pursuant hereto or in otherwise enforcing any of its rights, powers or remedies hereunder.
h)
Notices. Any and all notices or other communications or deliveries to be provided by the holders hereunder including, without
limitation, any Notice of Exercise, shall be in writing and delivered personally, by e-mail, or sent by a nationally recognized overnight
courier service, addressed to the Company, at 321 Farmington Road, Mocksville NC 27028, Attention: Jonathan Staffeldt, email address:
jstaffeldt@xxiicentury.com, or such other email address or address as the Company may specify for such purposes by notice to the Holder.
Any and all notices or other communications or deliveries to be provided by the Company hereunder shall be in writing and delivered personally,
by e-mail, or sent by a nationally recognized overnight courier service addressed to each Holder at the e-mail address or address of
such Holder appearing on the books of the Company. Any notice or other communication or deliveries hereunder shall be deemed given and
effective on the earliest of (i) the time of transmission, if such notice or communication is delivered via e-mail at the e-mail address
set forth in this Section prior to 5:30 p.m. (New York City time) on any date, (ii) the next Trading Day after the time of transmission,
if such notice or communication is delivered via e-mail at the e-mail address set forth in this Section on a day that is not a Trading
Day or later than 5:30 p.m. (New York City time) on any Trading Day, (iii) the second Trading Day following the date of mailing, if sent
by U.S. nationally recognized overnight courier service, or (iv) upon actual receipt by the party to whom such notice is required to
be given. To the extent that any notice provided hereunder constitutes, or contains, material, non-public information regarding the Company
or any subsidiaries, the Company shall simultaneously file such notice with the Commission pursuant to a Current Report on Form 8-K.
18
i)
Limitation of Liability. No provision hereof, in the absence of any affirmative action by the Holder to exercise this Warrant
to purchase Warrant Shares, and no enumeration herein of the rights or privileges of the Holder, shall give rise to any liability of
the Holder for the purchase price of any Common Stock or as a stockholder of the Company, whether such liability is asserted by the Company
or by creditors of the Company.
j)
Remedies. The Holder, in addition to being entitled to exercise all rights granted by law, including recovery of damages, will
be entitled to specific performance of its rights under this Warrant. The Company agrees that monetary damages would not be adequate
compensation for any loss incurred by reason of a breach by it of the provisions of this Warrant and hereby agrees to waive and not to
assert the defense in any action for specific performance that a remedy at law would be adequate.
k)
Successors and Assigns. Subject to applicable securities laws, this Warrant and the rights and obligations evidenced hereby shall
inure to the benefit of and be binding upon the successors and permitted assigns of the Company and the successors and permitted assigns
of Holder. The provisions of this Warrant are intended to be for the benefit of any Holder from time to time of this Warrant and shall
be enforceable by the Holder or holder of Warrant Shares.
l)
Amendment. This Warrant may be modified or amended or the provisions hereof waived with the written consent of the Company and
the Holder.
m)
Severability. Wherever possible, each provision of this Warrant shall be interpreted in such manner as to be effective and valid
under applicable law, but if any provision of this Warrant shall be prohibited by or invalid under applicable law, such provision shall
be ineffective to the extent of such prohibition or invalidity, without invalidating the remainder of such provisions or the remaining
provisions of this Warrant.
n)
Headings. The headings used in this Warrant are for the convenience of reference only and shall not, for any purpose, be deemed
a part of this Warrant.
********************
(Signature
Page Follows)
19
IN
WITNESS WHEREOF, the Company has caused this Warrant to be executed by its officer thereunto duly authorized as of the date first above
indicated.
22ND
CENTURY GROUP, INC.
By:
Name:
Lawrence Firestone
Title:
Chief Executive Officer
20
NOTICE
OF EXERCISE
To:
22ND
CENTURY GROUP, INC.
(1)
The undersigned hereby elects to purchase ________ Warrant Shares of the Company pursuant to the terms of the attached Warrant (only
if exercised in full), and tenders herewith payment of the exercise price in full, together with all applicable transfer taxes, if any.
(2)
Payment shall take the form of (check applicable box):
☐
in lawful money of the United States; or
☐
if permitted, the cancellation of such number of Warrant Shares as is necessary, in accordance with the formula set forth in subsection
2(c), to exercise this Warrant with respect to the maximum number of Warrant Shares purchasable pursuant to the cashless exercise procedure
set forth in subsection 2(c).
(3)
Please issue said Warrant Shares in the name of the undersigned or in such other name as is specified below:
_______________________________
The
Warrant Shares shall be delivered to the following DWAC Account Number:
_______________________________
_______________________________
_______________________________
_______________________________
(4)
Accredited Investor. The undersigned is an “accredited investor” as defined in Regulation D promulgated under the
Securities Act of 1933, as amended.
[SIGNATURE
OF HOLDER]
Name
of Investing Entity: ________________________________________________________________________
Signature
of Authorized Signatory of Investing Entity: _________________________________________________
Name
of Authorized Signatory: ___________________________________________________________________
Title
of Authorized Signatory: ____________________________________________________________________
Date:
________________________________________________________________________________________
EXHIBIT
B
ASSIGNMENT
FORM
(To
assign the foregoing Warrant, execute this form and supply required information. Do not use this form to purchase shares.)
FOR
VALUE RECEIVED, the foregoing Warrant and all rights evidenced thereby are hereby assigned to
Name:
(Please
Print)
Address:
(Please
Print)
Phone
Number:
Address:
Dated:
_______________ __, ______
Holder’s
Signature: ________________________________
Holder’s
Address: _________________________________
EX-10.1
EX-10.1
Filename: ex10-1.htm · Sequence: 4
Exhibit
10.1
22nd
Century Group, Inc.
321
Farmington Road
Mocksville,
North Carolina 27028
(336)
940-3769
Dated
as of June [ ], 2026
To
Holders of Common Stock Purchase Warrants
Re:
Inducement Offer to Exercise Common Stock Purchase Warrants
Dear
Holder:
22nd
Century Group, Inc. (the “Company”) is pleased pursuant to this letter agreement (this “Agreement”)
to offer to you the opportunity to exercise all or part of the warrants of the Company beneficially owned by you: (i) on August 27, 2025
and (ii) on March 23, 2026 (collectively, the “Existing Warrants”) as set forth on the signature page hereto (the
“Holder”), exercisable for the number shares of the Company’s common stock, par value $0.00001 per share, as
set forth in such Existing Warrants (the “Existing Warrant Shares”). The Existing Warrant Shares were registered on
a registration statement on Form S-3 (File Nos. 333-270473 and 333-294792). Capitalized terms not otherwise defined herein shall have
the meanings set forth in the Existing Warrants.
In
consideration for exercising the Existing Warrants held by you in part or in full for the number of Existing Warrant Shares set forth
on the signature page hereto in cash at a reduced exercise price $[*]1 per Existing Warrant (the “Warrant Exercise”),
the Company hereby offers to issue you or your designee a new common stock purchase warrant (the “New Warrant”) pursuant
to Section 4(a)(2) of the Securities Act of 1933, as amended (“Securities Act”), to purchase up to a quantity of shares
of Common Stock (the “New Warrant Shares”) equal to 100% of the number of Existing Warrant Shares issued pursuant
to the exercise of the Existing Warrants hereunder, which New Warrant shall be in the form attached hereto as Exhibit A. Each holder
agrees to exercise all of the Existing Warrants within one business day of this Agreement.
As
soon as reasonably practicable, but in any event no later than June 30, 2026, the Company shall file a registration statement on Form
S-3 (or other appropriate form if the Company is not then S-3 eligible) providing for the resale of the outstanding New Warrant Shares.
The Company shall use commercially reasonable efforts to cause such registration statement to become effective within 45 days following
the date of this Agreement (the date such registration statement is declared effective, the “Effectiveness Date”)
and to keep such registration statement effective at all times until no Holder owns any Shares or shares issuable upon exercise of the
Prefunded Warrants.
The
parties hereto hereby agree that the definition of “Stockholder Approval” means (i) such approval as may be required by the
applicable rules and regulations of the Nasdaq Capital Market (or any successor entity) from the stockholders of the Company with respect
to the transactions contemplated herein, including with respect to the issuance of the shares underlying the New Warrants, including
but not limited to with respect to a Dilutive Issuance and Share Combination Event Adjustment (as defined in the New Warrants) and (ii)
approval from the Company’s stockholders of an offering of the Company’s securities, including preferred stock and warrants
on substantially the same terms as the Securities under the Securities Purchase Agreement from March 20, 2026, to be completed within
three (3) months from the date of the stockholder meeting at which stockholder approval is obtained, in an aggregate amount not to exceed
$20 million, with the initial conversion price of such preferred stock to equal to the Nasdaq Minimum Price (as defined in Nasdaq Listing
Rule 5635(d)) and the initial exercise price of such warrants to equal the Nasdaq Minimum Price, in each case, as of the date the related
binding agreement is executed.
In
addition, the Company agrees to hold an annual or special meeting of stockholders within ninety (90) days following the date of this
Agreement for the purpose of obtaining Stockholder Approval, for the purpose of obtaining Stockholder Approval, with the recommendation
of the Company’s Board of Directors that such proposals are approved, and the Company shall solicit proxies from its stockholders
in connection therewith in the same manner as all other management proposals in such proxy statement and all management-appointed proxyholders
shall vote their proxies in favor of such proposals.
1
To equal the Nasdaq Minimum Price on the date of this Agreement.
The
original New Warrants will be delivered on the Closing Date (as defined below). Notwithstanding anything herein to the contrary, in the
event that the exercise of an Existing Warrant would otherwise cause you to exceed the applicable Beneficial Ownership Limitation set
forth in Section 2(e) of the Existing Warrants, the Company shall only issue such number of Existing Warrant Shares to you that would
not cause you to exceed the maximum number of Existing Warrant Shares permitted thereunder, with the balance to be held in abeyance until
notice from you that such balance (or portion thereof) may be issued in compliance with such Beneficial Ownership Limitation, which abeyance
shall be evidenced through the Existing Warrants which shall be deemed prepaid thereafter, and exercised pursuant to a Notice of Exercise
in the Existing Warrant (provided no additional exercise price shall be payable).
Expressly
subject to the paragraph immediately following this paragraph below, you may accept this offer by signing this letter below, and to exercise
all or part of the Existing Warrants, you may subsequently submit Notice(s) of Exercise on or before [ ] Eastern Time on June [ ], 2026.
Additionally,
the Company agrees to the representations, warranties and covenants set forth on Annex A attached hereto. You represent and warrant
that (i) you are an “accredited investor” as defined in Rule 501 of the Securities Act; (ii) you, either alone or together
with your representatives, have such knowledge, sophistication and experience in business and financial matters so as to be capable of
evaluating the merits and risks of the prospective investment in the securities offered herby, and have so evaluated the merits and risks
of such investment; (iii) you are able to bear the economic risk of an investment in such securities and, at the present time, are able
to afford a complete loss of such investment; and (iv) you have had the opportunity to review the transaction documents related to this
investment and the Company’s filings with the Commission and understand the Company has substantial doubt regarding its ability
to continue as a going concern, and have been afforded the following: the opportunity to ask such questions as you have deemed necessary
of, and to receive answers from, representatives of the Company concerning the terms and conditions of the offering of the securities
and the merits and risks of investing in the securities; access to information about the Company and its financial condition, results
of operations, business, properties, management and prospects sufficient to enable you to evaluate your investment, and the opportunity
to obtain such additional information that the Company possesses or can acquire without unreasonable effort or expense that is necessary
to make an informed investment decision with respect to the investment. You further agree that the New Warrants will contain restrictive
legends when issued, and subject to this Agreement and the obligation of the Company to register the New Warrant Shares under the terms
of the New Warrant, neither the New Warrant nor the New Warrant Shares will be registered under the Securities Act, except in the discretion
of the Company.
You
understand that the New Warrant will not be registered under the Securities Act upon issuance and that the Company will undertake to
register the New Warrant Shares under the Securities Act, pursuant to the terms of this letter. In furtherance thereof, the New Warrant
and each certificate evidencing New Warrant Shares, if, for any reason, the New Warrant Shares, if any, are not then currently covered
under an effective registration statement, shall bear a legend substantially similar to the following:
“[NEITHER]
THIS SECURITY [NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE] HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION
OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED
(THE “SECURITIES ACT”), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION
STATEMENT UNDER THE SECURITIES ACT OR PURSUANT TO AN AVAILABLE EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS
OF THE SECURITIES ACT AND IN ACCORDANCE WITH APPLICABLE STATE SECURITIES LAWS. [EACH OF] THIS SECURITY [AND THE SECURITIES ISSUABLE UPON
EXERCISE OF THIS SECURITY] MAY BE PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN ACCOUNT OR OTHER LOAN SECURED BY SUCH SECURITY.”
Certificates
evidencing New Warrant Shares shall not contain any legend (including the legend set forth above), (i) while a registration statement
covering the resale of such New Warrant Shares is effective under the Securities Act; (ii) following any sale of such New Warrant Shares
pursuant to Rule 144 under the Securities Act; (iii) if such New Warrant Shares are eligible for sale under Rule 144, without the requirement
for the Company to be in compliance with the current public information required under Rule 144 as to such New Warrant Shares and without
volume or manner-of-sale restrictions; (iv) if such New Warrant Shares may be sold under Rule 144 and the Company is then in compliance
with the current public information required under Rule 144 as to such New Warrant Shares; or (v) if such legend is not required under
applicable requirements of the Securities Act (including judicial interpretations and pronouncements issued by the staff of the Commission
and the earliest of clauses (i) through (v), the “Delegend Date”)). The Company shall cause its counsel to issue a
legal opinion to the transfer agent promptly after the Delegend Date if required by the Company and/or the transfer agent to effect the
removal of the legend hereunder, which opinion shall be in form and substance reasonably acceptable to you. If such New Warrant Shares
may be sold under Rule 144 without the requirement for the Company to be in compliance with the current public information required under
Rule 144 or if such legend is not otherwise required under applicable requirements of the Securities Act (including judicial interpretations
and pronouncements issued by the staff of the Commission) then such New Warrant Shares shall be issued free of all legends. The Company
agrees that following the Delegend Date or at such time as such legend is no longer required under this paragraph, it will, no later
than one (1) Trading Day following the delivery by you to the Company or the Transfer Agent of a certificate representing the New Warrant
Shares issued with a restrictive legend (such Trading Day, the “Legend Removal Date”), deliver or cause to be delivered
to you a certificate representing such New Warrant Shares that is free from all restrictive and other legends or, at your request shall
credit the account of your prime broker with the Depository Trust Company System as directed by you.
In
addition to your other available remedies, the Company shall pay to you, in cash, (i) as partial liquidated damages and not as a penalty,
for each $1,000 of New Warrant Shares (based on the VWAP of the shares of Common Stock on the date such New Warrant Shares are submitted
to the Transfer Agent) delivered for removal of the restrictive legend, $10 per Trading Day (increasing to $20 per Trading Day five (5)
Trading Days after such damages have begun to accrue) for each Trading Day after the Legend Removal Date until such certificate is delivered
without a legend and (ii) if the Company fails to (a) issue and deliver (or cause to be delivered) to you by the Legend Removal Date
a certificate representing the New Warrant Shares so delivered to the Company by you that is free from all restrictive and other legends
and (b) if after the Legend Removal Date you purchase (in an open market transaction or otherwise) shares of Common Stock to deliver
in satisfaction of a sale by you of all or any portion of the number of New Warrant Shares, or a sale of a number of shares of Common
Stock equal to all or any portion of the number of New Warrant Shares that you anticipated receiving from the Company without any restrictive
legend, then, an amount equal to the excess of your total purchase price (including brokerage commissions and other out-of-pocket expenses,
if any) for the shares of Common Stock so purchased (including brokerage commissions and other out-of-pocket expenses, if any) over the
product of (A) such number of New Warrant Shares that the Company was required to deliver to you by the Legend Removal Date multiplied
by (B) the lowest closing sale price of the shares of Common Stock on any Trading Day during the period commencing on the date of the
delivery by you to the Company of the applicable New Warrant Shares (as the case may be) and ending on the date of such delivery and
payment under this clause (ii).
On
or before 9:00 a.m. Eastern Time on June [ ], 2026, the Company shall file a Current Report on Form 8-K disclosing all material terms
of the transactions contemplated hereunder. From and after the filing of such Current Report on Form 8-K, the Company represents to you
that it shall have publicly disclosed all material, non-public information delivered to you by the Company, or any of their respective
officers, directors, employees or agents in connection with the transactions contemplated hereunder. In addition, effective upon the
issuance of such document(s), the Company acknowledges and agrees that any and all confidentiality or similar obligations under any agreement,
whether written or oral, between the Company, any of its subsidiaries or any of their respective officers, directors, agents, employees
or Affiliates on the one hand, and you and your Affiliates on the other hand, shall terminate.
The
Company represents, warrants and covenants that, upon acceptance of this offer, the shares underlying the Existing Warrants shall be
issued free of any legends or restrictions on resale by you, subject to the application of the Beneficial Ownership Limitation and any
Existing Warrant Shares being held in abeyance until notice from you that such balance (or portion thereof) may be issued in compliance
with such Beneficial Ownership Limitation and all of the Existing Warrant Shares shall be delivered electronically through the Depository
Trust Company within one (1) business day of the date the Company receives the payment of the aggregate exercise price of the Existing
Warrants (the “Closing Date”) (or, with respect to Existing Warrant Shares that would otherwise be in excess of the
Beneficial Ownership Limitation, within one (1) business day of the date on which the Company is notified by you that its ownership is
less than the Beneficial Ownership Limitation). The terms of the Existing Warrants, including but not limited to the obligations to deliver
the Existing Warrant Shares, shall otherwise remain in effect as if the acceptance of this offer were a formal Notice of Exercise (including
but not limited to any liquidated damages and compensation in the event of late delivery of the Existing Warrant Shares).
The
Company acknowledges and agrees that your obligations under this Agreement are several and not joint with the obligations of any other
holder (each, an “Other Holder”) of newly issued common stock purchase warrants of the Company offered and issued
to Other Holders pursuant to substantially similar agreements containing similar inducement offers under such other agreements related
to the exercise of such warrants as contained in this Agreement (“Other Warrant Exercise Agreements”), and you shall
not be responsible in any way for the performance of the obligations of any Other Holder or under any such Other Warrant Exercise Agreement.
Nothing contained in this letter agreement, and no action taken by you pursuant hereto, shall be deemed to constitute you and the Other
Holders as a partnership, an association, a joint venture or any other kind of entity, or create a presumption that you and the Other
Holders are in any way acting in concert or as a group with respect to such obligations or the transactions contemplated by this Agreement
and the Company acknowledges that you and the Other Holders are not acting in concert or as a group with respect to such obligations
or the transactions contemplated by this Agreement or any Other Warrant Exercise Agreement. The Company and you confirm that you have
independently participated in the negotiation of the transactions contemplated hereby with the advice of your own counsel and advisors.
You shall be entitled to independently protect and enforce your rights, including, without limitation, the rights arising out of this
Agreement, and it shall not be necessary for any Other Holder to be joined as an additional party in any proceeding for such purpose.
Series
B Preferred Stock Redemption Election. Each Holder participating in the Warrant Exercise shall have the option to elect, in the Holder’s
sole discretion, to direct that all or a portion of the aggregate proceeds received by the Company from such Holder’s exercise
of the Existing Warrants hereunder be applied by the Company to redeem shares of the Company’s Series B Convertible Preferred Stock
(the “Series B Preferred Stock”) held by such Holder, at a redemption price equal to the par value of such shares of Series
B Preferred Stock (the “Series B Redemption”). To make such election, a Holder must deliver written notice to the Company
(the “Redemption Election Notice”), in substantially the form set forth on the signature page hereto, specifying the number
of shares of Series B Preferred Stock to be so redeemed, no later than ten (10) calendar days following the Closing Date (the “Redemption
Election Deadline”). Any Redemption Election Notice delivered after the Redemption Election Deadline shall be null and void. If
a Holder timely delivers a Redemption Election Notice, the Company shall apply the applicable proceeds to consummate the Series B Redemption
as soon as commercially possibly but no later than five (5) business days following the Company’s receipt of such Redemption Election
Notice. For the avoidance of doubt, any Holder that does not deliver a Redemption Election Notice on or before the Redemption Election
Deadline shall be deemed to have waived the right to direct the application of such proceeds to the Series B Redemption.
Please
do not hesitate to call me if you have any questions.
Sincerely
yours,
22ND
CENTURY GROUP, INC.
By:
Name:
Title:
[Holder
Signature Page Follows]
Accepted
and Agreed by:
Name
of Holder: ________________________________________________________
Signature
of Authorized Signatory of Holder: _________________________________
Name
of Authorized Signatory: _______________________________________________
Title
of Authorized Signatory: ________________________________________________
Number
of Existing Warrants: _____________________________________
Aggregate
Warrant exercise price at the exercise price being exercised contemporaneously with signing this letter agreement: _________________
Existing
Warrants Beneficial Ownership Blocker: ☐ 4.99% or ☐ 9.99%
New
Warrants: _______________ (100% warrant coverage)
New
Warrants Beneficial Ownership Blocker: ☐ 4.99% or ☐ 9.99%
DTC
Instructions:
Series
B Preferred Stock Redemption Election (optional – must be delivered within 10 calendar days of Closing Date):
☐
The undersigned hereby elects to direct the Company to apply $_________________ of the proceeds from the Warrant Exercise to redeem
_________________ shares of Series B Preferred Stock held by the undersigned at par value.
[Holder
signature page to XXII Inducement Offer]
Annex
A
Representations,
Warranties and Covenants of the Company. The Company hereby makes the following representations and warranties to you:
(a)
SEC Reports. The Company has filed all reports, schedules, forms, statements and other documents required to be filed by the Company
under the Exchange Act, including pursuant to Section 13(a) or 15(d) thereof, for the one year preceding the date hereof (or such shorter
period as the Company was required by law or regulation to file such material) (the foregoing materials, including the exhibits thereto
and documents incorporated by reference therein “SEC Reports”). As of their respective dates, the SEC Reports complied
in all material respects with the requirements of the Exchange Act and none of the SEC Reports, when filed, contained any untrue statement
of a material fact or omitted to state a material fact required to be stated therein or necessary in order to make the statements therein,
in the light of the circumstances under which they were made, not misleading. The Company is not currently an issuer identified in Rule
144(i) under the Securities Act.
(b)
Authorization; Enforcement. The Company has the requisite corporate power and authority to enter into and to consummate the transactions
contemplated by this Agreement and otherwise to carry out its obligations hereunder and thereunder. The execution and delivery of this
Agreement by the Company and the consummation by the Company of the transactions contemplated hereby have been duly authorized by all
necessary action on the part of the Company and no further action is required by the Company, its board of directors or its stockholders
in connection therewith other than the Stockholder Approval (as defined in the New Warrant). This Agreement has been duly executed by
the Company and, when delivered in accordance with the terms hereof, will constitute the valid and binding obligation of the Company
enforceable against the Company in accordance with its terms, except (i) as limited by general equitable principles and applicable bankruptcy,
insolvency, reorganization, moratorium and other laws of general application affecting enforcement of creditors’ rights generally;
(ii) as limited by laws relating to the availability of specific performance, injunctive relief or other equitable remedies; and (iii)
insofar as indemnification and contribution provisions may be limited by applicable law.
(c)
No Conflicts. The execution, delivery and performance of this Agreement by the Company and the consummation by the Company of
the transactions contemplated hereby do not and will not: (i) conflict with or violate any provision of the Company’s certificate
of incorporation, as amended, bylaws or other organizational or charter documents; or (ii) conflict with, or constitute a default (or
an event that with notice or lapse of time or both would become a default) under, result in the creation of any liens, claims, security
interests, other encumbrances or defects upon any of the properties or assets of the Company in connection with, or give to others any
rights of termination, amendment, acceleration or cancellation (with or without notice, lapse of time or both) of, any material agreement,
credit facility, debt or other material instrument (evidencing Company debt or otherwise) or other material understanding to which such
Company is a party or by which any property or asset of the Company is bound or affected; or (iii) conflict with or result in a violation
of any law, rule, regulation, order, judgment, injunction, decree or other restriction of any court or governmental authority to which
the Company is subject (including federal and state securities laws and regulations), or by which any property or asset of the Company
is bound or affected, except, in the case of each of clauses (ii) and (iii), such as could not have or reasonably be expected to result
in a material adverse effect upon the business, prospects, properties, operations, condition (financial or otherwise) or results of operations
of the Company, taken as a whole, or in its ability to perform its obligations under this letter agreement.
(d)
Issuance of the New Warrants. The issuance of the New Warrants is duly authorized and, upon the execution of this Agreement by
the undersigned, will be duly and validly issued, fully paid and nonassessable, free and clear of all liens imposed by the Company, and
the New Warrant Shares, when issued in accordance with the terms of the New Warrants, will be validly issued, fully paid and nonassessable,
free and clear of all liens imposed by the Company. The Company has reserved from its duly authorized capital stock a number of shares
of Common Stock for issuance of the New Warrant Shares in full, subject to an increase in authorized shares of Common Stock.
(e)
Listing of Common Stock. The Company hereby agrees to use commercially reasonable efforts to maintain the listing or quotation
of the Common Stock on the Trading Market on which it is currently listed, and concurrently with the Closing, the Company shall apply
to list or quote all of the New Warrant Shares on such Trading Market and promptly secure the listing of all of the New Warrant Shares
on such Trading Market. The Company further agrees, if the Company applies to have the Common Stock traded on any other Trading Market,
it will then include in such application all of the New Warrant Shares, and will take such other action as is necessary to cause all
of the New Warrant Shares to be listed or quoted on such other Trading Market as promptly as possible. The Company will then take all
action reasonably necessary to continue the listing and trading of its Common Stock on a Trading Market and will comply in all respects
with the Company’s reporting, filing and other obligations under the bylaws or rules of the Trading Market. The Company agrees
to maintain the eligibility of the Common Stock for electronic transfer through the Depository Trust Company or another established clearing
corporation, including, without limitation, by timely payment of fees to the Depository Trust Company or such other established clearing
corporation in connection with such electronic transfer.
(f)
Filings, Consents and Approvals. The Company is not required to obtain any consent, waiver, authorization or order of, give any
notice to, or make any filing or registration with, any court or other federal, state, local or other governmental authority or other
Person in connection with the execution, delivery and performance by the Company of this letter agreement, other than: (i) the filings
required pursuant to this letter agreement, (ii) application(s) or notice to each applicable Trading Market for the listing of the New
Warrants and New Warrant Shares for trading thereon in the time and manner required thereby, (iii) the filing of Form D with the Commission
and such filings as are required to be made under applicable state securities laws, and (iv) Stockholder Approval.
(g)
Stockholder Meeting. The Company covenants that it shall use commercially reasonable efforts to hold an annual or a special meeting
of stockholders (“Stockholder Meeting”) on or prior to the date that is ninety(90) days following the date of this
Agreement for the purpose of obtaining Stockholder Approval, with the recommendation of the Company’s Board of Directors that proposals
subject to Stockholder Approval are approved, and the Company shall solicit proxies from its stockholders in connection therewith in
the same manner as all other management proposals in such proxy statement and all management-appointed proxyholders shall vote their
proxies in favor of such proposals. If the Company does not obtain Stockholder Approval at the first meeting, the Company shall call
a meeting every ninety (90) days thereafter to seek Stockholder Approval until the earlier of the date on which Stockholder Approval
is obtained or the New Warrants are no longer outstanding.
(h)
Form D; Blue Sky Filings. If required, the Company agrees to timely file a Form D with respect to the New Warrants and New Warrant
Shares as required under Regulation D and to provide a copy thereof, promptly upon request of any Holder. The Company shall take such
action as the Company shall reasonably determine is necessary in order to obtain an exemption for, or to qualify the New Warrants and
New Warrant Shares for, sale to the Holder at Closing under applicable securities or “Blue Sky” laws of the states of the
United States, and shall provide evidence of such actions promptly upon request of any Holder.
(i)
Standstill. From the date of this Agreement until 30 days after the later of (i) Stockholder Approval Date (as defined in the
New Warrant) and (ii) the Effectiveness Date, neither the Company nor any if its subsidiaries shall (i) issue, enter into any agreement
to issue or announce the issuance or proposed issuance of any shares of Common Stock (as defined in the New Warrant) or Common Stock
Equivalents (as defined in the New Warrant) or (ii) file any registration statement or any amendment or supplement thereto, other than
(a) as contemplated pursuant to this Agreement and (b) a Form S-8 registration statement for the Company’s benefit plans; provided
that for the avoidance of doubt, in no event shall the Company be restricted from the actions described above following 60 days after
the Stockholder Approval Date (as defined in the New Warrant).
EXHIBIT
A – FORM OF WARRANT
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v3.26.1
Cover
Jun. 08, 2026
Cover [Abstract]
Document Type
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Amendment Flag
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Amendment Description
This Amendment
No. 1 to the Current Report on Form 8-K (this “Amendment”) amends the Current Report on Form 8-K filed by 22nd Century Group,
Inc. (the “Company”) with the Securities and Exchange Commission on June 9, 2026 (the “Original Report”). This
Amendment is being filed solely to correct the exercise price of the Inducement Warrants disclosed in Item 1.01 of the Original Report
from $0.4626 to $3.57. Except as expressly set forth in this Amendment, all other information set forth in the Original Report remains
unchanged and is incorporated herein by reference.
Document Period End Date
Jun. 08, 2026
Current Fiscal Year End Date
--12-31
Entity File Number
001-36338
Entity Registrant Name
22nd
Century Group, Inc.
Entity Central Index Key
0001347858
Entity Tax Identification Number
98-0468420
Entity Incorporation, State or Country Code
NV
Entity Address, Address Line One
321
Farmington Road
Entity Address, City or Town
Mocksville
Entity Address, State or Province
NC
Entity Address, Postal Zip Code
27028
City Area Code
(336)
Local Phone Number
940-3769
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Trading Symbol
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Security Exchange Name
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