Company: XXII
Filing Date: 2025-12-30
Form Type: DEF 14A
Source: 0001493152-25-029651
Chunk: 24

Company: 22nd Century Group, Inc.
Filing Date: 2025-12-30
Form: DEF 14A
Chunk 24
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 potential issuance by the Company of common stock (or securities convertible into or exercisable for common stock), which equals 20% or more of the common stock or 20% or more of the voting power outstanding before the issuance. The sections of the Certificate of Designations above could result in the potential issuance of more than 19.99% of our outstanding common stock at below the Minimum Price under Nasdaq rules without approval of our stockholders.

Possible Effects of the Proposal

If the stockholders do not approve this Proposal 2, then the Series A Preferred conversion price will not change. 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. In addition, if stockholder approval is not obtained, the holders may require us to redeem the Series A Preferred at the Stated Value per share for cash. If approved, the Series A Preferred will be dilutive to current stockholders.

| Our Board of Directors recommends that the stockholders vote “FOR” Proposal 2 to             
 approve the issuance of shares upon the anti-dilution adjustments in the Series A Preferred. |

| PROXY STATEMENT | 13 |

<div align='center'>Proposal THREE:

APPROVAL OF THE ANTI-DILUTION ADJUSTMENTS in the AUGUST WARRANTS</div>

The board of directors has approved and recommends to the stockholders a proposal to approve the amendment to the August 2025 Warrants adding anti-dilution provisions pursuant to Rule 5635(d) of the Nasdaq Stock Market for the potential issuance of more than 19.99% of our outstanding common stock at below the Minimum Price under Nasdaq rules.

General

As previously disclosed on a current report on Form 8-K filed with SEC on August 25, 2025, we sold shares of Series A Preferred and warrants to purchase shares of Common Stock pursuant to a registered direct offering. The investors purchased approximately $10.65 million of shares of Series A Preferred and warrants. 9,460,661 of the warrants are currently exercisable at an exercise price of $1.97 per share of common stock and 567,641 of the warrants, issued as placement agent warrants in the offering, are currently exercisable for $2.167 and