UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d) of the

Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): August 22, 2025

22nd Century Group, Inc.

(Exact Name of Registrant as Specified in Charter)

Registrant’s telephone number, including area code: (716) 270-1523

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:

Securities registered pursuant to Section 12(b) of the Act:

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. ☐

On August 22, 2025, 22nd Century Group, Inc. (the “Company”) and certain investors (the “Investors”) entered into a securities purchase agreement (the “Securities Purchase Agreement”) with respect to the offer and sale of $10.65 million of shares of Series A Convertible Preferred Stock, stated value $1,000 per share (the “Series A Preferred Stock”), initially convertible into an aggregate of 4,863,013 shares of the Company’s common stock (the “Common Stock”) at a initial conversion price of $2.19 (subject to adjustment in certain circumstances following stockholder approval and with such adjustments subject to a floor price of $0.394) and warrants (the “Warrants”) to purchase shares of Common Stock pursuant to a registered direct offering (collectively, the “Offering”). The Investors purchased approximately $10.65 million of shares of Series A Preferred Stock and Warrants. The Warrants are immediately exercisable at an exercise price of $1.97 per share of Common Stock and expire on the date that is five (5) years after issuance. The Offering is expected to close on August 26, 2025, subject to the satisfaction of customary closing conditions. For a description of the terms of the Series A Preferred Stock, see Item 5.03 below.

The Securities Purchase Agreement provides that, subject to certain exceptions, until 45 days after the closing of the Offering, 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. The Securities Purchase Agreement also provides that certain of the Investors in the Offering have a right of participation in future equity or equity linked offerings by the Company for 9 months after no shares of Series A Preferred Stock are outstanding in an amount equal to 50% of such subsequent financing.

The Securities Purchase Agreement provides that, subject to certain exceptions, until no shares of Series A Preferred Stock are outstanding, the Company will be prohibited from effecting or entering into an agreement to effect any issuance by the Company or any of its subsidiaries of common stock or common stock equivalents (or a combination of units thereof) involving a Variable Rate Transaction (as defined in the Securities Purchase Agreement).

The net proceeds to the Company from the Offering, after deducting the fees of Dawson James Securities, Inc. (the “Placement Agent”) and the Company’s estimated offering expenses, are expected to be approximately $10 million. The Company expects to use the proceeds to repay it outstanding indebtedness with JGB and the balance for working capital.

The shares of Series A Preferred Stock, Warrants and the shares of Common Stock underlying the shares of Series A Preferred Stock and Warrants are being offered and sold pursuant to the Company’s Registration Statement on Form S-3 (Registration No. 333-270473) previously filed with the Securities and Exchange Commission (the “SEC”) and declared effective on March 31, 2023, the base prospectus included therein and the related prospectus supplement to be filed with the SEC.

The Company will pay the Placement Agent a cash fee of 6.0% of the gross proceeds from the Offering, an additional 6.0% cash fee of any cash exercise of the Warrants and agreed to reimburse the Placement Agent for its expenses, including the reimbursement of legal fees up to an aggregate of $25,000. The Company has also agreed to reimburse the legal fees of the lead Investor’s legal counsel, with $25,000 to be remitted up front and the remainder to be paid on or prior to Closing. In addition, the Company agreed to issue placement agent warrants to purchase an aggregate of 567,640 shares of common stock (the “Placement Agent Warrants”) with substantially the same terms as the Warrants, except that the exercise price of the Placement Agent Warrants shall be 110% of the exercise price of the Warrants.

The foregoing summaries of the terms of the Securities Purchase Agreement, the Warrants and the Placement Agent Warrants are subject to, and qualified in their entirety by, the forms of such documents attached hereto as Exhibits 10.1, 4.1, and 4.2, respectively, and incorporated herein by reference. Each of the Securities Purchase Agreement and the Warrants contains representations and warranties that the respective parties made to, and solely for the benefit of, the other parties thereto in the context of all of the terms and conditions of those agreements and in the context of the specific relationship between the parties. The provisions of the Securities Purchase Agreement, including the representations and warranties contained therein, are not for the benefit of any party other than the parties to such agreement or as stated therein and are not intended as a document for investors and the public to obtain factual information about the current state of affairs of the parties to the documents and agreements. Rather, investors and the public should look to other disclosures contained in the Company’s filings with the SEC.

A copy of the opinion of Foley & Lardner LLP relating to the legality of the issuance and sale of securities is attached hereto as Exhibit 5.1.

The description of the terms of the Series A Preferred Stock under Item 1.01 and Item 5.03 is incorporated herein by reference.

Prior to the closing of the Offering, the Company will file a Certificate of Designation of Preferences, Rights and Limitations with the Secretary of State of the State of Nevada designating 10,650 shares out of the authorized but unissued shares of its preferred stock as Series A Preferred Stock with a stated value of $1,000 per share (the “Series A Certificate of Designation”). The following is a summary of the principal terms of the Series A Preferred Stock as set forth in the Series A Certificate of Designation:

Dividends

The holders of Series A Preferred Stock will be entitled to dividends when and as declared by the board of directors of the Company (the “Board”), from time to time, in its sole discretion, which dividends will be paid by the Company out of funds legally available therefor, payable, subject to the conditions and other terms of the Certificate of Designations, in cash, in securities of the Corporation or using assets as determined by the Board on the stated value of such Preferred Stock.

Voting Rights

The shares of Series A Preferred Stock have no voting rights, except to the extent required by the applicable law. As long as any shares of Series A Preferred Stock are outstanding, the Company may not, without the approval of a majority of the then outstanding shares of Series A Preferred Stock (a) alter or change the powers, preferences or rights given to the Series A Preferred Stock, (b) alter or amend the Certificate of Incorporation or the bylaws of the Company in such a manner so as to materially adversely affect any rights given to the Series A Preferred Stock, (c) authorize or create any class of stock ranking as to dividends, redemption or distribution of assets upon a Liquidation (as defined below) senior to, or otherwise pari passu with, the Series A Preferred Stock, (d) increase the number of authorized shares of Series A Preferred Stock, or (e) enter into any agreement to do any of the foregoing.

Liquidation

Upon any liquidation, dissolution or winding-up of the Company, whether voluntary or involuntary (a “Liquidation”), the then holders of the Series A Preferred Stock are entitled to receive out of the assets available for distribution to stockholders of the Company an amount equal to either (i) 100% of the stated value or (ii) the amount the holder would receive if the Series A Preferred Stock had been converted into Common Stock; in each instance, prior to and in preference to the Common Stock or any other series of preferred stock.

Conversion

The Series A Preferred Stock is convertible into Common Stock at any time at a conversion price of $2.19 and, upon the receipt of stockholder approval, subject to adjustment for certain anti-dilution provisions set forth in the Series A Certificate of Designation, subject to a floor price of $0.394 (the “Series A Conversion Price”). The Company agreed to hold a meeting of stockholders within 90 days of closing to approve the issuance of the shares of Common Stock upon such anti-dilution adjustment. If stockholder approval is not obtained within 180 days, the holders may require the Company to redeem the Series A Preferred Stock at the Stated Value per share.

Conversion at the Option of the Holder

The Series A Preferred Stock is convertible at the then-effective Series A Conversion Price at the option of the holder at any time and from time to time.

Mandatory Conversion at the Option of the Company

If, at any time from and after issuance, (i) the closing price of the Common Stock equals or exceeds 200% of the then Conversion Price for 10 consecutive trading days and (ii) the daily dollar trading volume for the Common Stock exceeds $1,000,000 per day during such period, the Company may require the the holders to convert the Series A Preferred Stock into Common Stock at the Series A Conversion Price.

Beneficial Ownership Limitation

The Series A Preferred Stock cannot be converted to Common Stock if the holder and its affiliates would beneficially own more than 4.99% (or 9.99% at the election of the holder) of the outstanding Common Stock. However, any holder may increase or decrease such percentage to any other percentage not in excess of 9.99% upon notice to us, provided that any increase in this limitation will not be effective until 61 days after such notice from the holder to us and such increase or decrease will apply only to the holder providing such notice.

Preemptive Rights

No holders of Series A Preferred Stock will, as holders of Series A Preferred Stock, have any preemptive rights to purchase or subscribe for Common Stock or any of our other securities.

Redemption

At any time one year after the issuance date, the Company may redeem all or a portion of the shares of Series A Preferred Stock outstanding by delivering notice at least 30 calendar days prior equal to 110% of the Stated Value per share of Series A Preferred Stock being redeemed.

Negative Covenants

As long as any Series A Preferred Stock is outstanding, unless the holders of more than 50% of the then outstanding shares of Series A Preferred Stock shall have otherwise given prior written consent, the Company cannot, subject to certain exceptions enter into, create, incur, assume, guarantee or suffer to exist any indebtedness (as defined in the Certificate of Designations) exceeding $100,000.

Trading Market

There is no established trading market for any of the Series A Preferred Stock, and we do not expect a market to develop. We do not intend to apply for a listing for any of the Series A Preferred Stock on any securities exchange or other nationally recognized trading system. Without an active trading market, the liquidity of the Series A Preferred Stock will be limited.

The Series A Certificate of Designation is attached as Exhibit 3.1 hereto. The summary above is not intended to be complete and is qualified in its entirety by reference to such exhibit which is incorporated herein by reference.

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.