Company: XXII
Filing Date: 2025-06-10
Form Type: PRER14A
Source: 0001641172-25-014371
Chunk: 75

Company: 22nd Century Group, Inc.
Filing Date: 2025-06-10
Form: PRER14A
Chunk 75
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 will fully exercise under a Zero Exercise Price Exercise as it provides for two (2) shares of
common stock for no cash payment, as compared to one share or less upon a cash or cashless exercise. Accordingly, we do not expect
to receive any net proceeds from Warrant exercises.

Possible Effects of the Proposal

If the stockholders do not approve this Proposal 8, then the Warrants will not be exercisable. Additionally, the failure to obtain Stockholder Approval may discourage future investors from engaging in future financings with us. If these consequences occur, we may have difficulty finding alternative sources of capital to fund our operations in the future on terms favorable to us or at all. We can provide no assurance that we would be successful in raising funds pursuant to additional equity or debt financings.

If the stockholders approve this Proposal 8, the Warrants shall become immediately exercisable. The Company believes the issuance of the securities described in this Proposal No. 8 would result in the issuance of over 20% of the Company’s outstanding shares of Common Stock on a pre-transaction basis, as the number of shares issuable underlying the warrants (assuming a Zero Exercise Price Exercise) of 22,144,186 is approximately 192% of the total common shares outstanding of 11,507,622 as of May 16, 2025. As such, for so long as the Holders beneficially own a significant amount of shares of our Common Stock, it could significantly influence future Company decisions.

Our
stockholders will incur substantial dilution of their percentage ownership to the extent that the Holders fully exercise the May
1, 2025 Warrant Shares, as the warrants could have a reduced exercise price upon a dilutive issuance, or more likely as a result of
a Zero Exercise Price Exercise. Additionally, significant dilution could result from a Share Combination Event (as defined above),
including an adjustment to increase the number of shares of common stock underlying the warrants.

<div align='center'>Our Board of Directors recommends that the stockholders vote “FOR” Proposal 8 to approve the issuance of the shares of common stock upon exercise of the Warrants pursuant to Rule 5635(d) of the Nasdaq Stock Market.</div>

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<div align='center'>PROPOSAL NO.9

APPROVAL OFAN AMENDMENT TO THE OUTSTANDING CONVERTIBLE DEBENTURES PURSUANT TO RULES 5635(B) AND 5635(D) OF THE NASDAQ