22世纪集团股份有限公司美股招股说明书(2025-11-04版)

Up to $25,000,000 Common Stock We have entered into a sales agreement (the “Sales Agreement”) with Needham & Company, LLC (the “Sales Agent”), relating to the sale ofthe shares of our common stock offered by this prospectus supplement and the accompanying prospectus. In accordance with the terms of theSales Agreement, under this prospectus supplement and the accompanying prospectus, we may offer and sell shares of our common stock,$0.00001 par value, having an aggregate offering price of up to $25,000,000 from time to time through or to the Sales Agent, acting as ouragent or as principal. Our common stock is listed on the Nasdaq Capital Market under the symbol “XXII.” The closing price of our common stock on November 3,2025 was $1.55 per share. Sales of our common stock, if any, under this prospectus supplement and the accompanying prospectus may be made in sales deemed to be “atthe market offerings” as defined in Rule 415 promulgated under the Securities Act of 1933, as amended (the “Securities Act”). The Sales Agentis not required to sell any specific number or dollar amount of shares, but will act as our sales agent using commercially reasonable effortsconsistent with its normal trading and sales practices, on mutually agreed terms between the Sales Agent and us. There is no arrangement forfunds to be received in any escrow, trust or similar arrangement. The compensation to the Sales Agent for sales of our common stock under the Sales Agreement will be an amount equal to 3.00% of the grossproceeds of any sale of shares of our common stock under the Sales Agreement. See “Plan of Distribution” beginning on page S-11 foradditional information regarding the compensation to be paid to the Sales Agent. The amount of net proceeds we will receive from this offering,if any, will depend upon the actual number of shares of our common stock sold and the market price at which such shares are sold. Becausethere is no minimum offering amount required as a condition to close this offering, the actual total public offering amount, commissions and netproceeds to us, if any, are not determinable at this time. In connection with the sale of our common stock on our behalf, the Sales Agent will be deemed to be an “underwriter” within the meaning ofthe Securities Act and the compensation of the Sales Agent will be deemed to be underwriting commissions or discounts. We have also agreedto provide indemnification and contribution to the Sales Agent with respect to certain civil liabilities, including liabilities under the SecuritiesAct. Investing in our common stock involves a high degree of risk. You should read this prospectus supplement and the accompanyingprospectus carefully before you make your investment decision. See “Risk Factors” beginning on page S-6 of this prospectussupplement, the accompanying prospectus, and the other documents we file or have filed with the Securities and Exchange Commissionthat are incorporated by reference in this prospectus supplement and in the accompanying prospectus, for a discussion of the factorsyou should consider before investing in our common stock. Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of these securitiesor determined if this prospectus supplement or the accompanying prospectus is truthful or complete. Any representation to thecontrary is a criminal offense. Needham & Company The date of this prospectus supplement is November 4, 2025 TABLE OF CONTENTS Prospectus SupplementAbout This Prospectus SupplementS-1“Forward-Looking Information”S-2Prospectus Supplement SummaryS-4The OfferingS-5Risk FactorsS-6Use of ProceedsS-8DilutionS-9Plan of DistributionS-11Legal MattersS-11ExpertsS-12Where You Can Find More InformationS-12ProspectusABOUT THIS PROSPECTUS1RISK FACTORS1“FORWARD-LOOKING” INFORMATION122ND CENTURY GROUP, INC.3USE OF PROCEEDS4DILUTION5SECURITIES TO BE OFFERED6DESCRIPTION OF DEBT SECURITIES7DESCRIPTION OF CAPITAL STOCK13DESCRIPTION OF WARRANTS17DESCRIPTION OF SUBSCRIPTION RIGHTS18DESCRIPTION OF SECURITIES PURCHASE CONTRACTS19DESCRIPTION OF UNITS20PLAN OF DISTRIBUTION21WHERE YOU CAN FIND MORE INFORMATION23LEGAL MATTERS24EXPERTS24S-i We are offering to sell, and are seeking offers to buy, the securities only in jurisdictions where such offers and sales are permitted. Thedistribution of this prospectus supplement and the accompanying prospectus and the offering of the securities in certain jurisdictionsmay be restricted by law. Persons outside the United States who come into possession of this prospectus supplement and theaccompanying prospectus must inform themselves about and observe any restrictions relating to the offering of the securities and thedistribution of this prospectus supplement and the accompanying prospectus outside the United States. This prospectus supplementand the accompanying prospectus do not constitute, and may not be used in connection with, an offer to sell, or a solicitation