XXII / 22nd Century Group, Inc. - تصريحات هيئة الأوراق المالية والبورصات، التقرير السنوي، بيان الوكيل

August 22, 2025

Exhibit 16.1 August 22, 2025 Securities and Exchange Commission 100 F Street, N.E. Washington, DC 20549-7561 Dear Sirs: We have read 22nd Century Group, Inc.’s statements included under Item 4.01 of its Form 8-K dated August 22, 2025, and are in agreement with the statements contained therein concerning our firm in response to Item 304(a) of Regulation S-K. Sincerely, /s/ Freed Maxick, P.C. Freed

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 Grou

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) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission File

10,650 Shares of Series A Convertible Preferred Stock Common Warrants to Purchase up to 9,460,661 Shares of Common Stock Placement Agent Warrants to Purchase up to 567,641 Shares of Common Stock Up to 14,891,315 Shares of Common Stock Underlying Such

Prospectus Supplement (To Prospectus dated March 31, 2023) Filed Pursuant to Rule 424(b)(5) Registration No.

SECURITIES PURCHASE AGREEMENT

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of August 22, 2025, between 22nd Century Group, Inc., a Nevada corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”). WHEREAS, subject to the terms and conditions

22nd Century Group, Inc. CERTIFICATE OF DESIGNATION OF PREFERENCES, RIGHTS AND LIMITATIONS SERIES A CONVERTIBLE PREFERRED STOCK

Exhibit 1.1 22nd Century Group, Inc. CERTIFICATE OF DESIGNATION OF PREFERENCES, RIGHTS AND LIMITATIONS OF SERIES A CONVERTIBLE PREFERRED STOCK The undersigned, Lawrence D. Firestone does hereby certify that: 1. He is the Chief Executive Officer, of 22nd Century Group, Inc., a Nevada corporation (the “Corporation”). 2. The Corporation is authorized to issue 10,000,000 shares of preferred stock, 2,5

PLACEMENT AGENT COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc.

Exhibit 4.2 PLACEMENT AGENT COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc. Warrant Shares: [] Issue Date: [ ], 2025 THIS PLACEMENT AGENT 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 the date set fo

COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc.

Exhibit 4.1 COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc. Warrant Shares: [] Issue Date: [ ], 2025 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 the date set forth above (the “Initial Exercise

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 Grou

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) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission File

Calculation of Filing Fee Tables Form S-8 (Form Type) 22nd Century Group, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) 22nd Century Group, Inc.

As filed with the Securities and Exchange Commission on August 15, 2025.

As filed with the Securities and Exchange Commission on August 15, 2025. File No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 22nd CENTURY GROUP, INC. (Exact Name of Registrant as Specified in Its Charter) Nevada 98-0468420 (State or Other Jurisdiction of Incorporation or Organization) (I.R.S. Employer

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Quarterly Period Ended June 30, 2025 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period From to Commission File Number: 001-36338 22nd C

Master Services Agreement with Murphy Oil USA, Inc. dated June 23, 2025 (filed herewith)

Exhibit 10.2 [REDACTED] = Pursuant to Item 601(b)(10) of Regulation S-K, portions of this exhibit have been omitted as the registrant has determined certain confidential information contained in this document, marked by brackets, is (i) not material and (ii) would be competitively harmful if publicly disclosed. MASTER SERVICES AGREEMENT This Master Services Agreement (hereinafter the “Agreement”)

22nd CENTURY GROUP, INC. CONDENSED CONSOLIDATED BALANCE SHEETS (amounts in thousands, except share and per-share data)

Exhibit 99.1 22nd Century Group Reports Second Quarter 2025 Financial Results VLN® Early Adoption Commercial Activity Expands with Two Partner Brand Launches in Progress – Smoker Friendly and Pinnacle Commenced Pinnacle VLN® Stocking Shipments for Almost 1,000 Locations of Top-5 C-Store Customer, Additional Locations to Come Significantly Expanded State Authorizations for both Reduced Nicotine Con

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 14, 2025 22nd Century Grou

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 14, 2025 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

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): July 15, 2025 22nd Century Group,

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): July 15, 2025 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 N

Up to 8,588,811 Shares of Common Stock Issuable Upon Exercise of Warrants

Prospectus Filed Pusuant to Rule 424(b)(3) Registration No. 333-288216 Up to 8,588,811 Shares of Common Stock Issuable Upon Exercise of Warrants This prospectus relates to the resale from time to time by the selling stockholders named in this prospectus under the caption “Selling Stockholders,” or the Selling Stockholders, of up to 8,588,811 shares of our common stock, par value $0.00001 per share

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769 June 25, 2025 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549 Attn: Bradley Ecker Re: 22nd Century Group, Inc. Registration Statement on Form S-3 File No. 333-288216 Acceleration Request Requested Date: Monday, June 30, 2025 Requested Time: 4:00 P.M. E

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): June 23, 2025 22nd Century Group,

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): June 23, 2025 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 N

22nd Century Announces Second Partner VLN Product Deal

Exhibit 99.1 22nd Century Announces Second Partner VLN Product Deal as Part of Major Pinnacle Brand Expansion Agreement with Top-5 C-Store Chain Launching New Pinnacle VLN and Moist Snuff Products in More Than 1,700 Stores Across 27 States MOCKSVILLE, N.C., June 24, 2025 — 22nd Century Group, Inc. (Nasdaq: XXII), the only tobacco products company that is leading the fight against nicotine by offer

As filed with the Securities and Exchange Commission on June 20, 2025

As filed with the Securities and Exchange Commission on June 20, 2025 Registration No.

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 22ND CENTURY GROUP, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Share Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common stock, par v

Amendment to Certificate of Incorporation of the Company (incorporated by reference to Exhibit 3.1 to the Form 8-K filed with the Commission on June 16, 2025).

Exhibit 3.1

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): June 16, 2025 22nd Century Group,

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): June 16, 2025 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 N

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Amendment No. 2 (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Amendment No.

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769 June 9, 2025 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549 Attn: Eranga Dias Re: 22nd Century Group, Inc. Revised Preliminary Proxy Statement on Schedule 14A Filed June 6, 2025 File No. 001-36338 Ladies and Gentlemen: On behalf of 22nd Century Group,

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769 June 6, 2025 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549 Attn: Eranga Dias Re: 22nd Century Group, Inc. Preliminary Proxy Statement on Schedule 14A Filed May 22, 2025 File No. 001-36338 Ladies and Gentlemen: On behalf of 22nd Century Group, Inc. (t

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Amendment No. 1 (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Amendment No.

Letter Agreement with JGB

Exhibit 10.1 JGB Collateral, LLC JGB Capital Offshore Ltd. JGB Capital LP JGB Partners LP c/o JGB Management, Inc. 246 Post Road East, 2nd Floor Westport, CT 06880 May 22, 2025 Via Federal Express and E-mail 22nd Century Group, Inc. 321 Farmington Rd. Mocksville, NC 27028 E-mail: [email protected] Re: Securities Purchase Agreement dated March 3, 2023, (the “SPA”) between 22nd Century Group, In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

Entry into a Material Definitive Agreement, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): May 22, 2025 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 Nu

7,089,497 Shares of Common Stock Up to 4,182,596 Shares of Common Stock Issuable Upon Exercise of Warrants

Prospectus Filed Pusuant to Rule 424(b)(3) Registration No. 333-287095 7,089,497 Shares of Common Stock Up to 4,182,596 Shares of Common Stock Issuable Upon Exercise of Warrants This prospectus relates to the resale from time to time by the selling stockholders named in this prospectus under the caption “Selling Stockholders,” or the Selling Stockholders, of up to 11,272,093 shares of our common s

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769 May 19, 2025 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549 Attn: Eranga Dias Re: 22nd Century Group, Inc. Registration Statement on Form S-3 File No. 333-287095 Acceleration Request Requested Date: Thursday, May 22, 2025 Requested Time: 9:30 A.M. Eas

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): May 13, 2025 22nd Century Group,

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): May 13, 2025 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 Nu

22nd CENTURY GROUP, INC. CONDENSED CONSOLIDATED BALANCE SHEETS (amounts in thousands, except share and per-share data)

Exhibit 99.1 22nd Century Group Reports First Quarter 2025 Financial Results Sales Increase Approximately 50% Sequentially as 2025 Growth Strategy Drives New Sales Activity with Both Internal and External Brand Assets Across Multiple Categories Preparing First VLN® Partner Brand Shipments with Smoker Friendly and Others Filings Made for New Reduced Nicotine Content and Conventional Product Authori

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Quarterly Period Ended March 31, 2025 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period From to Commission File Number: 001-36338 22nd

107 Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 22ND CENTURY GROUP, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Share Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common stock, par v

As filed with the Securities and Exchange Commission on May 8, 2025

As filed with the Securities and Exchange Commission on May 8, 2025 Registration No.

Form of Inducement Warrant

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 REGISTR

Form of Inducement Letter

Exhibit 10.1 22nd Century Group, Inc. 321 Farmington Road Mocksville, North Carolina 27028 (716) 270-1523 Dated as of April [ ], 2025 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 exer

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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): April 29, 2025 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

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ☒ Annual Report under Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2024 ☐ Transition Report und

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ☒ Annual Report under Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2024 or ☐ Transition Report under Section 13 or 15(d) of the Securities Exchange Act of 1934 Commission File Number: 001-36338 22nd Century Group, Inc. (Exact name of registrant

Form of Warrant Amendment

Exhibit 4.2 AMENDMENT TO COMMON STOCK PURCHASE WARRANT This Amendment to Common Stock Purchase Warrant (this “Amendment”) is made and entered into as of April [ ], 2025 (the “Amendment Date”), by and among 22nd Century Group, Inc., a Nevada corporation (the “Company”), and the undersigned holder (the “Holder”), and constitutes an amendment to that certain Common Stock Purchase Warrant issued by th

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): April 17, 2025 22nd Century Group

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): April 17, 2025 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

UNITED STATES DISTRICT COURT FOR THE WESTERN DISTRICT OF NEW YORK

Exhibit 99.1 UNITED STATES DISTRICT COURT FOR THE WESTERN DISTRICT OF NEW YORK IN RE 22ND CENTURY GROUP, INC. DERIVATIVE LITIGATION Lead Case No. 1:19-cv-00479-JLS EXHIBIT C NOTICE OF PENDENCY AND PROPOSED SETTLEMENT OF STOCKHOLDER DERIVATIVE ACTIONS TO: ALL RECORD HOLDERS AND BENEFICIAL OWNERS OF 22ND CENTURY GROUP, INC. (“22ND CENTURY” OR THE “COMPANY”) COMMON STOCK AS OF MARCH 4, 2025. PLEASE R

Stipulation and Agreement of Settlement

Exhibit 99.2

Results of Operations and Financial Condition, Financial Statements and Exhibits

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): March 20, 2025 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

22nd CENTURY GROUP, INC. CONDENSED CONSOLIDATED BALANCE SHEETS (amounts in thousands, except share and per-share data)

Exhibit 99.1 22nd Century Group Reports Fourth Quarter and Full Year 2024 Financial Results Launches 2025 Growth Strategy Leveraging Both Internal and External Brand Assets Across Multiple Categories Announces First VLN® Partner Brands with Smoker Friendly Ready for Shipment in Q2 2025, Additional Partner VLN® Brands in Discussion MOCKSVILLE, N.C., March 20, 2025 — 22nd Century Group, Inc. (Nasdaq

Description of Securities Registered Pursuant to Section 12

EXHIBIT 4.1 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 As of December 31, 2023, 22nd Century Group, Inc. (“we” or “our”) had one class of securities, our common stock, par value $0.00001 per share (“Common Stock”), registered under Section 12 of the Securities Exchange Act of 1934, as amended. The following description of our

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ Annual Report under Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2024 ☐ Transition Report under Section 13 or 15(

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ Annual Report under Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2024 or ☐ Transition Report under Section 13 or 15(d) of the Securities Exchange Act of 1934 Commission File Number: 001-36338 22nd Century Group, Inc. (Exact name of registrant as

Master Services Agreement and Addendum #1 with Smoker Friendly International, LLC dated January 1, 2025.

Exhibit 10.12 MASTER SERVICES AGREEMENT This Master Services Agreement (hereinafter the “Agreement”) is made and entered into as of January 1, 2025 (the “Effective Date”), by and between NASCO PRODUCTS, LLC, a Delaware limited liability company, having its principal place of business at 321 Farmington Road, Mocksville, North Carolina 27028 (“Supplier”); 22ND CENTURY GROUP, INC., a Nevada Corporati

SUBSIDIARIES OF 22nd CENTURY GROUP, INC.

EXHIBIT 21.1 SUBSIDIARIES OF 22nd CENTURY GROUP, INC. Name State of Formation Percentage 22nd Century Limited, LLC Delaware 100% Goodrich Tobacco Company, LLC Delaware 100% Heracles Pharmaceuticals, LLC Delaware 100% NASCO Products, LLC North Carolina 100% Botanical Genetics, LLC Delaware 100% 22nd Century Group Europe B.V. Amsterdam 100% 22nd Century Group Canada, Inc. Canada 100% 22nd Century Ho

JOINT FILING AGREEMENT February 14, 2025

EX-99.1 2 ea023119601ex99-122ndcent.htm JOINT FILING AGREEMENT Exhibit 99.1 JOINT FILING AGREEMENT February 14, 2025 Pursuant to and in accordance with the Securities Exchange Act of 1934, as amended (the “Act”), and the rules and regulations thereunder, each party hereto hereby agrees to the joint filing, on behalf of each of them, of any filing required by such party under Section 13 or Section

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (336) 940-3769 February 6, 2025 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549 Attn: Jenny O’Shanick Re: 22nd Century Group, Inc. Registration Statement on Form S-3 File No. 333-284644 Acceleration Request Requested Date: Tuesday, February 11, 2025 Requested Time: 9

As filed with the Securities and Exchange Commission on February 5, 2025

As filed with the Securities and Exchange Commission on February 5, 2025 Registration No.

22nd Century Group, Inc.

22nd Century Group, Inc. February 5, 2025 Securities and Exchange Commission Division of Corporation Finance 100 F. Street, N.E. Washington, D.C. 20549 Attention: Ms. Jenny O’Shanick Mr. Jay Ingram Re: 22nd Century Group, Inc. Registration on Form S-3 Filed January 31, 2025 File No. 333-284644 This letter is in response to your comment letter dated February 4, 2025. Your comment is reproduced belo

As filed with the Securities and Exchange Commission on January 31, 2025.

As filed with the Securities and Exchange Commission on January 31, 2025. File No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 22nd CENTURY GROUP, INC. (Exact Name of Registrant as Specified in Its Charter) Nevada 98-0468420 (State or Other Jurisdiction of Incorporation or Organization) (I.R.S. Employer

As filed with the Securities and Exchange Commission on January 31, 2025

As filed with the Securities and Exchange Commission on January 31, 2025 Registration No.

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 22ND CENTURY GROUP, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Share Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common stock, par v

Filing Fee Exhibit (filed herewith).

EXHIBIT 107 Calculation of Filing Fee Tables Form S-8 (Form Type) 22nd Century Group, Inc.

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): January 21, 2025 22nd Century Gro

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): January 21, 2025 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

22nd Century Regains Full Compliance with Nasdaq Continued Listing Standards

Exhibit 99.1 22nd Century Regains Full Compliance with Nasdaq Continued Listing Standards MOCKSVILLE, N.C., January 27, 2025 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company that is leading the fight against nicotine and believes smokers should have a choice about their nicotine consumption, today announced that it has received formal written notice from The Nasdaq Stock Marke

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): January 13, 2025 22nd Century Gro

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): January 13, 2025 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

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): January 1, 2025 22nd Century Grou

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): January 1, 2025 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

22nd Century Group Signs New, Expanded License and Manufacturing Agreement with Smoker Friendly

Exhibit 99.1 22nd Century Group Signs New, Expanded License and Manufacturing Agreement with Smoker Friendly Agreement covers 11 existing brands, supports launch 8 additional premium brands with Smoker Friendly retail and dealer locations Creates foundation to launch additional reduced nicotine content brands in 2025 MOCKSVILLE, N.C., January 7, 2025 — 22nd Century Group, Inc. (Nasdaq: XXII), a to

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Material Modification to Rights of Security Holders, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing

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): December 16, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fi

Amendment to Certificate of Incorporation of the Company (incorporated by reference to Exhibit 3.1 to the Form 8-K filed with the Commission on December 17, 2024).

Exhibit 3.1

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): December 6, 2024 22nd Century Gro

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): December 6, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

Joint Filing Agreement (filed herewith).

EX-99.1 2 ea022343001ex99-122ndcen.htm JOINT FILING AGREEMENT Exhibit 99.1 JOINT FILING AGREEMENT December 3, 2024 Pursuant to and in accordance with the Securities Exchange Act of 1934, as amended (the “Act”), and the rules and regulations thereunder, each party hereto hereby agrees to the joint filing, on behalf of each of them, of any filing required by such party under Section 13 or Section 16

XXII / 22nd Century Group, Inc. / Reda Joseph - AMENDMENT NO. 3 TO SCHEDULE 13G Passive Investment

SC 13G/A 1 ea0223430-13ga3reda22ndcen.htm AMENDMENT NO. 3 TO SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No.3)* 22nd Century Group, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 90137F301 (CUSIP Number) November 26, 2024 (Date of Event Which

XXII / 22nd Century Group, Inc. / Anson Funds Management LP - SC 13G/A Passive Investment

SC 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G (Rule 13d-102) (Amendment No.

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 12, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fi

Three Months Ended

Exhibit 99.1 22nd Century Group Reports Third Quarter 2024 Financial Results Remains on Path to Cash Positive Operations in Q1 2025 Commencing Growth Strategy Leveraging Both Internal and External Brand Assets Across Multiple Categories MOCKSVILLE, N.C., November 12, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company that is leading the fight against nicotine dependence and

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Quarterly Period Ended September 30, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period From to Commission File Number: 001-36338 2

Up to 28,354,914 Shares of Common Stock Issuable Upon Exercise of Pre-Funded Warrants Up to 65,264,802 Shares of Common Stock Issuable Upon Exercise of Warrants

Prospectus Filed Pusuant to Rule 424(b)(3) Registration No. 333-282963 Up to 28,354,914 Shares of Common Stock Issuable Upon Exercise of Pre-Funded Warrants Up to 65,264,802 Shares of Common Stock Issuable Upon Exercise of Warrants This prospectus relates to the resale from time to time by the selling stockholders named in this prospectus under the caption “Selling Stockholders,” or the Selling St

107          Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 22ND CENTURY GROUP, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Share Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common stock, par v

As filed with the Securities and Exchange Commission on November 1, 2024

As filed with the Securities and Exchange Commission on November 1, 2024 Registration No.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6I(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

4.24         Form of Warrant (incorporated by reference to Exhibit 4.2 to the Company’s Form 8-K filed with the Commission on October 24, 2024).

Exhibit 4.2 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 REGISTR

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): October 23, 2024 22nd Century Gro

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): October 23, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

4.25         Form of Pre-Funded Warrant (incorporated by reference to Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on October 24, 2024).

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 REGISTR

4.23         Form of Placement Agent Warrant (incorporated by reference to Exhibit 4.3 to the Company’s Form 8-K filed with the Commission on October 24, 2024)

Exhibit 4.3 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 REGISTR

Form of Securities Purchase Agreement, dated October 23, 2024, by and between 22nd Century Group, Inc. and each of the Purchasers (as defined therein).

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of October 23, 2024, between 22nd Century Group, Inc., a Nevada corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”). WHEREAS, subject to the terms and condition

JOINT FILING AGREEMENT PURSUANT TO RULE 13d-1(k)(1)

EX-1 2 c110379ex1.htm Exhibit 1 JOINT FILING AGREEMENT PURSUANT TO RULE 13d-1(k)(1) The undersigned acknowledge and agree that the foregoing statement on Schedule 13G is filed on behalf of each of the undersigned and that all subsequent amendments to this statement on Schedule 13G shall be filed on behalf of each of the undersigned without the necessity of filing additional joint filing statements

XXII / 22nd Century Group, Inc. / Iroquois Capital Management, LLC Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2. (Amendment No. )* 22nd Century Group Inc. (Name of Issuer) Common Stock, par value $0.00001 per share (Title of Class of Securities) 90137F301 (CUSIP Number) October 11, 202

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): October 11, 2024 22nd Century Gro

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): October 11, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

Form of Securities Purchase Agreement, dated October 11, 2024, by and between 22nd Century Group, Inc. and each of the Purchasers (as defined therein).

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of October 11, 2024, between 22nd Century Group, Inc., a Nevada corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”). WHEREAS, subject to the terms and condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6I(2)) ☐ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

14,266,666 Shares of Common Stock

Prospectus Supplement (To Prospectus dated March 31, 2023) Filed Pursuant to Rule 424(b)(5) Registration No.

4.21         Form of Placement Agent Warrant (incorporated by reference to Exhibit 4.2 to the Company’s Form 8-K filed with the Commission on October 15, 2024)

Exhibit 4.2 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 REGISTR

4.22         Form of Warrant (incorporated by reference to Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on October 15, 2024).

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 REGISTR

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): October 10, 2024 22nd Century Gro

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): October 10, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

Letter Agreement with JGB

Exhibit 10.1 JGB Collateral, LLC JGB Capital Offshore Ltd. JGB Capital LP JGB Partners LP c/o JGB Management, Inc. 246 Post Road East, 2nd Floor Westport, CT 06880 October 10, 2024 Via Federal Express and E-mail 22nd Century Group, Inc. 321 Farmington Rd. Mocksville, NC 27028 E-mail: [email protected] Re: Securities Purchase Agreement dated March 3, 2023, (the “SPA”) between 22nd Century Group

XXII / 22nd Century Group, Inc. / Castaldo Gregory - SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* 22nd Century Group Inc. (Name of Issuer) Common Stock, par value $0.00001 per share (Title of Class of Securities) 90137F301 (CUSIP Number) September 29, 2024 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate t

Joint Filing Agreement (filed herewith).

EX-99.1 2 ea021712801ex99-122ndcen.htm JOINT FILING AGREEMENT Exhibit 99.1 JOINT FILING AGREEMENT October 8, 2024 Pursuant to and in accordance with the Securities Exchange Act of 1934, as amended (the “Act”), and the rules and regulations thereunder, each party hereto hereby agrees to the joint filing, on behalf of each of them, of any filing required by such party under Section 13 or Section 16

XXII / 22nd Century Group, Inc. / Reda Joseph - AMENDMENT NO. 2 TO SCHEDULE 13G Passive Investment

SC 13G/A 1 ea0217128-13ga2reda22ndcen.htm AMENDMENT NO. 2 TO SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 2)* 22nd Century Group, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 90137F301 (CUSIP Number) September 29, 2024 (Date of Event Whi

22nd Century Regains Compliance with Nasdaq Stockholders’ Equity Requirement

Exhibit 99.1 22nd Century Regains Compliance with Nasdaq Stockholders’ Equity Requirement MOCKSVILLE, N.C., October 8, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company that is leading the fight against nicotine and believes smokers should have a choice about their nicotine consumption, today announced that it has received formal written notice from The Nasdaq Stock Market

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): October 2, 2024 22nd Century Grou

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): October 2, 2024 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

5,153,508 Shares of Common Stock

Prospectus Supplement (To Prospectus dated March 31, 2023) Filed Pursuant to Rule 424(b)(5) Registration No.

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): September 27, 2024 22nd Century G

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): September 27, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission F

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): September 30, 2024 22nd Century G

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): September 30, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission F

4.18         Form of Warrant (incorporated by reference to Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on September 30, 2024).

  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 REG

4.20         Form of Warrant (incorporated by reference to Exhibit 4.3 to the Company’s Form 8-K filed with the Commission on September 30, 2024).

Exhibit 4.3 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 REGISTR

Form of Inducement Letter

Exhibit 10.2 22nd Century Group, Inc. 321 Farmington Road Mocksville, North Carolina 27028 (716) 270-1523 Dated as of September [ ], 2024 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

Form of Securities Purchase Agreement, dated September 27, 2024, by and between 22nd Century Group, Inc. and each of the Purchasers (as defined therein).

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of September 27, 2024, between 22nd Century Group, Inc., a Nevada corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”). WHEREAS, subject to the terms and conditi

4.17         Form of Placement Agent Warrant (incorporated by reference to Exhibit 4.2 to the Company’s Form 8-K filed with the Commission on September 30, 2024).

Exhibit 4.2 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 REGISTR

4.19         Form of Placement Agent Warrant (incorporated by reference to Exhibit 4.4 to the Company’s Form 8-K filed with the Commission on September 30, 2024).

Exhibit 4.4 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 REGISTR

1,399,776 Shares of Common Stock

Prospectus Filed Pursuant to Rule 424(b)(3) Registration No. 333-282157 1,399,776 Shares of Common Stock This prospectus relates to the resale from time to time by the selling stockholders named in this prospectus under the caption “Selling Stockholders,” or the Selling Stockholders, of up to 1,399,776 shares of our common stock, par value $0.00001 per share, or the Shares. We will not receive any

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (716) 270-1523

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (716) 270-1523 September 23, 2024 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549 Attn: Jenny O’Shanick Re: 22nd Century Group, Inc. Registration Statement on Form S-3 File No. 333-282157 Acceleration Request Requested Date: Wednesday, September 25, 2024 Requested Ti

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 22ND CENTURY GROUP, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Share Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common stock, par v

As filed with the Securities and Exchange Commission on September 16, 2024

As filed with the Securities and Exchange Commission on September 16, 2024 Registration No.

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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): September 13, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission F

4.16         Form of Warrant (incorporated by reference to Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on September 13, 2024).

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 REGISTR

Form of Warrant Purchase Agreement

Exhibit 10.1 Warrant PURCHASE AGREEMENT This Warrant Purchase Agreement (this “Agreement”) is dated as of September 13, 2024, between 22md Century Group, Inc., a Nevada corporation (the “Company”), and the purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser”) WHEREAS, subject to the terms and conditions set forth in this Agreement and pursua

Payment Agreement with NCSU

  Exhibit 10.1   [***] = Pursuant to Item 601(b)(10) of Regulation S-K, portions of this exhibit have been omitted as the registrant has determined certain confidential information contained in this document, marked by brackets, is (i) not material and (ii) would be competitively harmful if publicly disclosed. PAYMENT AGREEMENT   This Payment Agreement (the “Payment Agreement”) is by and between N

XXII Investor Presentation September 2024

Exhibit 99.2 XXII Investor Presentation September 2024 VLN - Helps You Smoke Less ® Except for historical information, all of the statements, expectations, and assumptions contained in this presentation are forward - looking statements, including but not limited to our business outlook Forward - looking statements typically contain terms such as “anticipate,” “believe,” “consider,” “continue,” “co

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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): September 5, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fi

22nd Century Satisfies IP Licensing and Sponsored Research Obligations to NCSU through 2025 in an Equity Transaction

Exhibit 99.1 22nd Century Satisfies IP Licensing and Sponsored Research Obligations to NCSU through 2025 in an Equity Transaction MOCKSVILLE, N.C., September 9, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company leading the fight against nicotine addiction with its FDA authorized 95% less nicotine brand VLN®, today announced an agreement to fund all intellectual property, l

XXII / 22nd Century Group, Inc. / Reda Joseph - AMENDMENT NO. 1 TO SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* 22nd Century Group, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 90137F301 (CUSIP Number) August 27, 2024 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate

Joint Filing Agreement (filed herewith).

EX-99.1 2 ea021368301ex99-122ndcen.htm JOINT FILING AGREEMENT Exhibit 99.1 JOINT FILING AGREEMENT September 5, 2024 Pursuant to and in accordance with the Securities Exchange Act of 1934, as amended (the “Act”), and the rules and regulations thereunder, each party hereto hereby agrees to the joint filing, on behalf of each of them, of any filing required by such party under Section 13 or Section 1

22nd Century Raises $1.68 Million in Regulation A Offering, Amends Senior Secured Credit Facility

Exhibit 99.1 22nd Century Raises $1.68 Million in Regulation A Offering, Amends Senior Secured Credit Facility MOCKSVILLE, N.C., August 28, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company focused on nicotine harm reduction and contract manufacturing, today announced that it has secured an additional $1.68 million in gross proceeds from institutional investors through its

4.15         Form of Warrant (incorporated by reference to Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on August 28, 2024).

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 REGISTR

Form of Warrant Purchase Agreement

Exhibit 10.2 Warrant PURCHASE AGREEMENT This Warrant Purchase Agreement (this “Agreement”) is dated as of August 27, 2024, between 22nd Century Group, Inc., a Nevada corporation (the “Company”), and the purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser”) WHEREAS, subject to the terms and conditions set forth in this Agreement and pursuant

Letter Agreement with JGB

Exhibit 10.1 JGB Collateral, LLC JGB Capital Offshore Ltd. JGB Capital LP JGB Partners LP c/o JGB Management, Inc. 246 Post Road East, 2nd Floor Westport, CT 06880 August 27, 2024 Via Federal Express and E-mail 22nd Century Group, Inc. 500 Seneca Street, Suite 507 Buffalo, New York 14204 E-mail: [email protected] Re:         Securities Purchase Agreement dated March 3, 2023, (the “SPA”) bet

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 27, 2024 22nd Century Grou

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 27, 2024 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

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 20, 2024 22nd Century Grou

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 20, 2024 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

22nd Century Group to Participate in the Emerging Growth Virtual Conference on August 21, 2024

Exhibit 99.1 22nd Century Group to Participate in the Emerging Growth Virtual Conference on August 21, 2024 MOCKSVILLE, N.C. / August 20, 2024 / 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company focused on nicotine harm reduction and contract manufacturing, today announced that it will provide a brief corporate update as part of the Emerging Growth Virtual Conference on Wednesday

Financial Statements and Exhibits, Entry into a Material Definitive Agreement

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 16, 2024 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

22nd Century Group, Inc. 321 Farmington Road Mocksville, North Carolina 27028 (716) 270-1523 37,500,000 Shares of Common Stock

Filed Pursuant to Rule 253(g)(3) Registration No. 024-12477 OFFERING CIRCULAR 22nd Century Group, Inc. 321 Farmington Road Mocksville, North Carolina 27028 (716) 270-1523 37,500,000 Shares of Common Stock By this offering circular (the “Offering Circular”), 22nd Century Group, Inc., a Nevada corporation, is offering on a “best-efforts” basis a maximum of 37,500,000 shares of its common stock, par

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Quarterly Period Ended June 30, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period From to Commission File Number: 001-36338 22nd C

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 13, 2024 22nd Century Grou

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 13, 2024 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

Three Months Ended

Exhibit 99.1 22nd Century Group Reports Second Quarter 2024 Financial Results Path to Cash Positive Operations in Q1 2025 Continued Fiscal Discipline with 2Q24 Financial Results Reduced Net Debt by ~$6.3 Million Year-to-Date MOCKSVILLE, N.C., August 13, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII) today announced results for the second quarter ended June 30, 2024, and provided an update on recen

EXPLANATORY NOTE

EXPLANATORY NOTE 22nd Century Group, Inc., a Nevada corporation (the “Company”) has prepared this Amendment No. 1 to Form 1-A (“Amendment”) solely for the purpose of filing the Opinion and Consent of Foley & Lardner LLP as Exhibits 11.2 and 12.1. Accordingly, this Amendment consists only of this explanatory note, the signature page to the Form 1-A, the exhibit index, and the exhibits referenced th

ATTORNEYS AT LAW

Exhibit 12.1 ATTORNEYS AT LAW One INDEPENDENT DRIVE JACKSONVILLE, FLORIDA 32202 904.359.2000 TEL 904.359.8700 FAX www.foley.com CLIENT/MATTER NUMBER 045952-0199 22nd Century Group, Inc. August 8, 2024 321 Farmington Road, Mocksville North Carolina 27028 Ladies and Gentlemen: We have served as counsel to 22nd Century Group, a Nevada corporation (the “Company”), in connection with the filing on Augu

Century Group, Inc.

22nd Century Group, Inc. 321 Farmington Rd Mocksville, NC 27028 August 8, 2024 VIA EDGAR Office of Manufacturing Division of Corporation Finance Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Attention: Patrick Fullem Re: 22nd Century Group, Inc. (the “Company”) Offering Statement on Form 1-A Filed August 2, 2024 (the “Offering Statement”) Commission File No. 024-1247

NOTICE TO INVESTORS

Exhibit 4.1 NOTICE TO INVESTORS THIS INVESTMENT INVOLVES A HIGH DEGREE OF RISK, SUITABLE ONLY FOR PERSONS WHO CAN BEAR THE ECONOMIC RISK FOR AN INDEFINITE PERIOD OF TIME AND WHO CAN AFFORD TO LOSE THEIR ENTIRE INVESTMENT. INVESTORS SHOULD FURTHER UNDERSTAND THAT THIS INVESTMENT IS ILLIQUID AND IS EXPECTED TO CONTINUE TO BE ILLIQUID FOR AN INDEFINITE PERIOD OF TIME. THE SECURITIES OFFERED HEREBY HA

PRELIMINARY OFFERING CIRCULAR DATED AUGUST 2, 2024

PRELIMINARY OFFERING CIRCULAR DATED AUGUST 2, 2024 An offering statement pursuant to Regulation A relating to these securities has been filed with the Securities and Exchange Commission.

CONSENT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

Exhibit 11.1 CONSENT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM We consent to the inclusion in this Registration Statement on Form 1-A of our report dated March 28, 2024, relating to our audit of the consolidated financial statements appearing in the Annual Report on Form 10-K of 22nd Century Group, Inc. for the year ended December 31, 2023. We also consent to the reference to our firm under

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Other Events

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): July 30, 2024 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 N

22nd Century Appoints Robert Manfredonia as Executive Vice President of Sales and Marketing

Exhibit 99.1 22nd Century Appoints Robert Manfredonia as Executive Vice President of Sales and Marketing Almost 30 years of experience in regulated consumer products sales MOCKSVILLE, N.C., July 30, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company focused on nicotine harm reduction and contract manufacturing, today announced the appointment of Robert Manfredonia as Execut

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): July 16, 2024 22nd Century Group,

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): July 16, 2024 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 N

As filed with the Securities and Exchange Commission on July 10, 2024.

As filed with the Securities and Exchange Commission on July 10, 2024. File No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 22nd CENTURY GROUP, INC. (Exact Name of Registrant as Specified in Its Charter) Nevada 98-0468420 (State or Other Jurisdiction of Incorporation or Organization) (I.R.S. Employer Id

Filing Fee Exhibit (filed herewith).

EXHIBIT 107 Calculation of Filing Fee Tables Form S-8 (Form Type) 22nd Century Group, Inc.

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

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): June 28, 2024 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 N

22nd Century Reduces Debt by Additional $1.5 Million via Payment from GVB

Exhibit 99.1 22nd Century Reduces Debt by Additional $1.5 Million via Payment from GVB MOCKSVILLE, N.C., June 25, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company focused on nicotine harm reduction and contract manufacturing, today announced a $1.5 million reduction in its secured debt via a paydown of the GVB secured promissory note. The amount was paid by GVB directly t

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): June 24, 2024 22nd Century Group,

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): June 24, 2024 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 N

Other Events

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): June 3, 2024 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 Nu

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

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): May 27, 2024 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 Nu

22nd CENTURY GROUP, INC. CONDENSED CONSOLIDATED BALANCE SHEETS (amounts in thousands, except share and per-share data)

Exhibit 99.1 22nd Century Group Reports First Quarter 2024 Financial Results New Contracts to Boost Second Quarter Revenue Reduced Operating Costs, Improved Cash Position Reduced ~$8.0 Million of Outstanding Debt and Liabilities for Equity Exchanges in Q2 2024 MOCKSVILLE, N.C., May 15, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company focused on nicotine harm reduction, to

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): May 15, 2024 22nd Century Group,

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): May 15, 2024 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 Nu

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Quarterly Period Ended March 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period From to Commission File Number: 001-36338 22nd

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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): May 10, 2024 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 Nu

May 2024 Exchange agreement with JGB

Exhibit 10.2 EXCHANGE AGREEMENT This EXCHANGE AGREEMENT (this “Agreement”) is made effective as of May 10, 2024, by and between (i) JGB Partners, LP (“JGB Partners”), JGB Capital, LP (“JGB Capital”) and JGB Capital Offshore Ltd. (“JGB Offshore” and collectively with JGB Partners and JGB Capital, the “Holders” and each a “Holder”), (ii) 22nd Century Group, Inc., a Nevada corporation (the “Company”)

4.14         Form of Pre-Funded Warrant (incorporated by reference to Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on May 10, 2024).

Exhibit 4.1 PRE-FUNDED COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc. Warrant Shares: [] THIS PRE-FUNDED 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 date of issuance (the “Initial

May 2024 Letter Agreement with JGB

Exhibit 10.1 JGB Collateral, LLC JGB Capital Offshore Ltd. JGB Capital LP JGB Partners LP c/o JGB Management, Inc. 246 Post Road East, 2nd Floor Westport, CT 06880 May 10, 2024 Via Federal Express and E-mail 22nd Century Group, Inc. 321 Farmington Rd Mocksville, NC 27028 E-mail: [email protected] Re: Securities Purchase Agreement dated March 3, 2023, (as amended, the “SPA”) between 22nd C

1,850,958 Shares of Common Stock Up to 7,290,012 Shares of Common Stock Issuable Upon Exercise of Warrants

Prospectus Filed Pursuant to Rule 424(b)(3) Registration No. 333-279046 1,850,958 Shares of Common Stock Up to 7,290,012 Shares of Common Stock Issuable Upon Exercise of Warrants This prospectus relates to the resale from time to time by the selling stockholders named in this prospectus under the caption “Selling Stockholders,” or the Selling Stockholders, of up to 9,140,970 shares of our common s

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (716) 270-1523

22nd Century Group, Inc. 321 Farmington Road Mocksville, NC 27028 (716) 270-1523 May 6, 2024 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549 Attn: Mr. Eranga Dias Re: 22nd Century Group, Inc. Registration Statement on Form S-3 Filed May 1, 2024 File No. 333-279046 Acceleration Request Requested Date: Thursday, May 9, 2024 Requested

107           Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 22ND CENTURY GROUP, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Share Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common stock, par v

As filed with the Securities and Exchange Commission on May 1, 2024

As filed with the Securities and Exchange Commission on May 1, 2024 Registration No.

4.12         Form of Common Warrant (incorporated by reference to Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on April 30, 2024).

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 REGISTR

22nd Century Eliminates $5.2 Million of Debt in Above-Market Equity Transaction

Exhibit 99.1 22nd Century Eliminates $5.2 Million of Debt in Above-Market Equity Transaction Improves Balance Sheet, Eliminates Future Omnia Interest Expense and Increases Shareholder Equity MOCKSVILLE, N.C., April 30, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company focused on nicotine harm reduction, today announced that it has entered into a binding letter of agreement

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): April 29, 2024 22nd Century Group

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): April 29, 2024 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

4.11         Form of Omnia Pre-Funded Warrant (incorporated by reference to Exhibit 4.2 to the Company’s Form 8-K filed with the Commission on April 30, 2024).

Exhibit 4.2 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 REGISTR

General Release and Settlement Agreement

Exhibit 10.1 GENERAL RELEASE AND SETTLEMENT AGREEMENT This General Release and Settlement Agreement (the “Agreement”) is by and between Omnia Capital LP (“Omnia”), and 22nd Century Group, Inc., a Nevada corporation, and its subsidiaries (collectively, the “Company”), effective as of April 29, 2024 (the “Effective Date”). Omnia and the Company are collectively referred to herein as the “parties” or

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

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): April 18, 2024 22nd Century Group

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): April 18, 2024 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

XXII / 22nd Century Group, Inc. / Reda Joseph - SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.)* 22nd Century Group, Inc. (Name of Issuer) Common Shares (Title of Class of Securities) 90137F301 (CUSIP Number) April 12, 2024 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Sc

4.9           Form of April 2024 Warrant (Incorporated by reference from Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on April 9, 2024).

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 REGISTR

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): April 9, 2024 22nd Century Group,

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): April 9, 2024 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 N

4.10         Form of Pre-Funded Warrant (incorporated by reference to Exhibit 4.2 to the Company’s Form 8-K filed with the Commission on April 9, 2024).

Exhibit 4.2 PREFUNDED COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc. Warrant Shares: [] THIS PREFUNDED 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 [ ], 2024 (the “Initial Exercise Date”)

4.10         Form of April 2024 Placement Agent Warrant (Incorporated by reference from Exhibit 4.3 to the Company’s Form 8-K filed with the Commission on April 9, 2024).

Exhibit 4.3 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 REGISTR

1,855,000 Shares of Common Stock Pre-Funded Warrants to Purchase up to 125,000 Shares of Common Stock Up to 125,000 Shares of Common Stock underlying such Pre-Funded Warrants

Prospectus Supplement (To Prospectus dated March 31, 2023) Filed Pursuant to Rule 424(b)(5) Registration No.

Form of Securities Purchase Agreement, dated April 8, 2024, by and between 22nd Century Group, Inc. and each of the Purchasers (as defined therein).

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of April 8, 2024, between 22nd Century Group, Inc., a Nevada corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”). WHEREAS, subject to the terms and conditions s

Letter Agreement with JGB

Exhibit 10.1 JGB Collateral, LLC JGB Capital Offshore Ltd. JGB Capital LP JGB Partners LP c/o JGB Management, Inc. 246 Post Road East, 2nd Floor Westport, CT 06880 April 5, 2024 Via Federal Express and E-mail 22nd Century Group, Inc. 500 Seneca Street, Suite 507 Buffalo, New York 14204 E-mail: [email protected] Re: Securities Purchase Agreement dated March 3, 2023, (the “SPA”) between 22nd

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): April 6, 2024 22nd Century Group,

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): April 6, 2024 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 N

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): April 4, 2024 22nd Century Group,

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): April 4, 2024 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 N

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Material Modification to Rights of Security Holders, Financial Statements and Exhibits

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): March 28, 2024 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

Amendment to Certificate of Incorporation of the Company (incorporated by reference to Exhibit 3.1 to the Form 8-K filed with the Commission on April 3, 2024).

Exhibit 3.1 Business Entity - Filing Acknowledgement 03/28/2024 Work Order Item Number: W2024032800269-3569191 Filing Number: 20243945981 Filing Type: Amendment After Issuance of Stock Filing Date/Time: 3/28/2024 8:00:00 AM Filing Page(s): 3 Indexed Entity Information: Entity ID: E0607512005-3 Entity Name: 22ND CENTURY GROUP, INC. Entity Status: Active Expiration Date: None Commercial Registered A

Compensation Recovery Policy

Exhibit 97.1 22nd Century Group, Inc. Compensation Recovery Policy 1. Purpose. The purpose of this Compensation Recovery Policy (this “Policy”) is to describe the circumstances under which 22nd Century Group, Inc. (the “Company”) is required to or shall have the right to recover certain compensation paid to certain employees and independent contractors. Any references in compensation plans, agreem

Description of Securities Registered Pursuant to Section 12

EXHIBIT 4.1 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 As of December 31, 2023, 22nd Century Group, Inc. (“we” or “our”) had one class of securities, our common stock, par value $0.00001 per share (“Common Stock”), registered under Section 12 of the Securities Exchange Act of 1934, as amended. The following description of our

Insider Trading Policy

Exhibit 19.1 Insider Trading Policy 22nd Century Group, Inc. This Insider Trading Policy (the “Policy”) applies to officers, employees, consultants and directors (the “Associates”) and immediate family members of, and other individuals who share a household with, an Associate (together with the Associates, the “Covered Persons”) of 22nd Century Group, Inc. and its subsidiaries (collectively, the “

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ Annual Report under Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2023 ☐ Transition Report under Section 13 or 15(

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ Annual Report under Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2023 or ☐ Transition Report under Section 13 or 15(d) of the Securities Exchange Act of 1934 Commission File Number: 001-36338 22nd Century Group, Inc. (Exact name of registrant as

SUBSIDIARIES OF 22nd CENTURY GROUP, INC.

EXHIBIT 21.1 SUBSIDIARIES OF 22nd CENTURY GROUP, INC. Name State of Formation Percentage 22nd Century Limited, LLC Delaware 100% Goodrich Tobacco Company, LLC Delaware 100% Heracles Pharmaceuticals, LLC Delaware 100% NASCO Products, LLC North Carolina 100% Botanical Genetics, LLC Delaware 100% 22nd Century Group Europe B.V. Amsterdam 100% 22nd Century Group Canada, Inc. Canada 100% 22nd Century Ho

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): March 28, 2024 22nd Century Group

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): March 28, 2024 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

22nd CENTURY GROUP, INC. CONDENSED CONSOLIDATED BALANCE SHEETS (amounts in thousands, except per-share data)

Exhibit 99.1 22nd Century Group (XXII) Reports Fourth Quarter 2023 Financial Results MOCKSVILLE, N.C., March 28, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII), a tobacco products company focused on nicotine harm reduction, today reported results for the fourth quarter ended December 31, 2023, and provided an update on recent business highlights. Fourth quarter results and recent business activiti

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Submission of Matters to a Vote of Security Holders

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): February 15, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fi

XXII / 22nd Century Group, Inc. / Anson Funds Management LP - SC 13G Passive Investment

SC 13G SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G (Rule 13d-102) (Amendment No.

JOINT FILING AGREEMENT

EX-99.1 2 d632622dex991.htm EX-99.1 EXHIBIT 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, the undersigned agree to the joint filing on behalf of each of them of a Statement on Schedule 13G (including any and all amendments thereto) with respect to the Common Stock, $0.00001 par value, of 22nd Century Group, Inc., a Nevada corpor

22nd Century Group Announces Reduction in Board Compensation Reduced Cost Structure Expected to Save more than $1Million Annually in 2024, Aligns Board with Corporate-Wide Lean Operating Commitment

Exhibit 99.1 22nd Century Group Announces Reduction in Board Compensation Reduced Cost Structure Expected to Save more than $1Million Annually in 2024, Aligns Board with Corporate-Wide Lean Operating Commitment MOCKSVILLE, N.C., February XX, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII) (the “Company” or “22nd Century”), a biotechnology company focused on utilizing advanced plant technologies to

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): February 9, 2024 22nd Century Gro

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): February 9, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

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): January 23. 2024 22nd Century Gro

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): January 23. 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

22nd Century Group Announces Partial Adjournment of Annual Meeting for Proposal 2, All Other Proposals Passed Transforming Business into Lean Operating Base, Extending Cash Runway, Shareholder Meeting to Re-convene February 15

Exhibit 99.1 22nd Century Group Announces Partial Adjournment of Annual Meeting for Proposal 2, All Other Proposals Passed Transforming Business into Lean Operating Base, Extending Cash Runway, Shareholder Meeting to Re-convene February 15 MOCKSVILLE, N.C., January 24, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII) (the “Company” or “22nd Century”), a biotechnology company focused on utilizing adv

Press Release dated January 24, 2024.

Exhibit 99.1 22nd Century Group Announces Partial Adjournment of Annual Meeting for Proposal 2, All Other Proposals Passed Transforming Business into Lean Operating Base, Extending Cash Runway, Shareholder Meeting to Re-convene February 15 MOCKSVILLE, N.C., January 24, 2024 — 22nd Century Group, Inc. (Nasdaq: XXII) (the “Company” or “22nd Century”), a biotechnology company focused on utilizing adv

Financial Statements and Exhibits, Other Events, Submission of Matters to a Vote of Security Holders

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): January 24, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

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): January 24, 2024 22nd Century Gro

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): January 24, 2024 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

JGB Amendment Agreement, dated December 22, 2023 (filed herewith).

Exhibit 10.2 AMENDMENT AGREEMENT This Amendment Agreement (the “Agreement”), dated as of December 22, 2023, is made by and between (i) JGB Partners, LP (“JGB Partners”), JGB Capital, LP (“JGB Capital”) and JGB Capital Offshore Ltd. (“JGB Offshore” and collectively with JGB Partners and JGB Capital, the “Holders” and each a “Holder”), (ii) 22nd Century Group, Inc., a Nevada corporation (the “Compan

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Completion of Acquisition or Disposition of Assets, Unregistered Sales of Equity Securities

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): December 22, 2023 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fi

22nd Century Group Completes Sale of Hemp/Cannabis Franchise Sale Will Significantly Reduce Operating Expenses, Ultimately Reduce Debt by $5.2 Million

Exhibit 99.1 22nd Century Group Completes Sale of Hemp/Cannabis Franchise Sale Will Significantly Reduce Operating Expenses, Ultimately Reduce Debt by $5.2 Million BUFFALO, N.Y., December 28, 2023 — 22nd Century Group, Inc. (Nasdaq: XXII) (the “Company” or “22nd Century”), a biotechnology company focused on utilizing advanced plant technologies to improve health and wellness, today announced it ha

UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL STATEMENTS 22nd Century Group, Inc. and Subsidiaries Introduction to Unaudited Pro Forma Condensed Consolidated Financial Statements

Exhibit 99.2 UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL STATEMENTS 22nd Century Group, Inc. and Subsidiaries Introduction to Unaudited Pro Forma Condensed Consolidated Financial Statements The following pro forma condensed consolidated financial statements are based on information currently available and have been prepared using certain assumptions and estimates. These unaudited pro form

Amendment to Equity Purchae Agreement, dated December 22, 2023 (filed herewith).

Exhibit 10.1 Execution Version AMENDMENT TO EQUITY PURCHASE AGREEMENT This Amendment to EQUITY PURCHASE AGREEMENT (this “Amendment”), dated as of December 22, 2023, is made by and between 22nd Century Group, Inc., a Nevada corporation (“22nd Century”), ESI Holdings, LLC, a Nevada limited liability company (“ESI,” and together with 22nd Century, the “Seller”), and Specialty Acquisition Corporation,

4.2           Form of Amended Original Issue Discount Senior Secured Debentures dated March 3, 2023 (incorporated by reference to Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on December 28, 2023).

Exhibit 4.1 EXECUTION VERSION NEITHER THIS SECURITY NOR THE SECURITIES ISSUABLE HEREUNDER 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 REGISTRAT

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

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): December 21, 2023 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6I(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6I(2)) ☐ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

4.5           Form of Inducement Warrant (incorporated by reference to Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on November 29, 2023).

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 REGISTR

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): November 28, 2023 22nd Century Gr

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): November 28, 2023 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fi

Form of Inducement Letter

Exhibit 10.1 22nd Century Group, Inc. 500 Seneca Street, Suite 508 Buffalo, New York (716) 270-1523 Dated as of November [ ], 2023 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 exercis

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): November 20, 2023 22nd Century Gr

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): November 20, 2023 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fi

Equity Purchase Agreement, dated November 20, 2023.

Exhibit 10.1 [Execution Version] Equity Purchase Agreement by and among 22nd Century Group, Inc., ESI Holdings, LLC and Specialty Acquisition Corporation dated as of November 20, 2023 Equity Purchase Agreement This Equity Purchase Agreement (this “Agreement”), dated as of November 20, 2023, is entered into by and between 22nd Century Group, Inc., a Nevada corporation (“22nd Century”), ESI Holdings

22nd Century Group Enters into Agreement to Sell Hemp/Cannabis Franchise -Sale Expected to Result in Immediate and Significant Reduction in Operating Costs and Cash Requirements-

Exhibit 99.1 22nd Century Group Enters into Agreement to Sell Hemp/Cannabis Franchise -Sale Expected to Result in Immediate and Significant Reduction in Operating Costs and Cash Requirements- BUFFALO, N.Y., November 27, 2023 (Globe Newswire) — 22nd Century Group, Inc. (Nasdaq: XXII) (the “Company” or “22nd Century”), a leading biotechnology company focused on utilizing advanced plant technologies

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): November 7, 2023 22nd Century Gro

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): November 7, 2023 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

License Agreement dated November 2, 2023.

Exhibit 10.1 [***] = Pursuant to Item 601(b)(10) of Regulation S-K, portions of this exhibit have been omitted as the registrant has determined certain confidential information contained in this document, marked by brackets, is (i) not material and (ii) would be competitively harmful if publicly disclosed. LICENSE AGREEMENT THIS License Agreement is entered into this 2nd day of November, 2023 (“Ef

###

Exhibit 99.1 22nd Century Group (XXII) Expands Reduced Nicotine Content Tobacco IP with Latest Technology License Additional Exclusive License with NCSU Further Expands Reduced Nicotine Content Plant Breeding Capabilities BUFFALO, N.Y., November 7, 2023 (Globe Newswire) — 22nd Century Group, Inc. (Nasdaq: XXII), a leading biotechnology company focused on utilizing advanced plant technologies to im

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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): November 2, 2023 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

Retention Agreement between the Company and R. Hugh Kinsman dated August 20, 2023, as amended

EXHIBIT 10.2 RETENTION AGREEMENT This Retention Agreement (this “Agreement”) is made this 20th day of August, 2023 (the “Effective Date”), by and between 22nd Century Group, Inc., a Nevada corporation (the “Company”) and R. Hugh Kinsman (the “Employee”). WHEREAS, as a material inducement for the Employee’s continued employment with the Company, the Company desires to provide the Employee with a Re

22nd CENTURY GROUP, INC. CONDENSED CONSOLIDATED BALANCE SHEETS (amounts in thousands, except per-share data)

Exhibit 99.1 22nd Century Group (XXII) Reports Third Quarter 2023 Financial Results ● Third quarter 2023 net revenue of $17.8 million ● Expanded VLN® availability to more than 4,550 stores in 19 states ● Proposed FDA menthol ban regulation now undergoing review at OMB ● GVB bulk ingredient volume of 49,000 kg shipped ● Initiated over $15 million in annualized operating cost reductions ● Reduced pr

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Quarterly Period Ended September 30, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period From to Commission File Number: 001-36338 2

Retention Agreement between the Company and John Miller dated August 23, 2023

EXHIBIT 10.1 RETENTION AGREEMENT This Retention Agreement (this “Agreement”) is made this 23rd day of August, 2023 (the “Effective Date”), by and between 22nd Century Group, Inc., a Nevada corporation (the “Company”) and John Miller (the “Employee”). WHEREAS, as a material inducement for the Employee’s continued employment with the Company, the Company desires to provide the Employee with a Retent

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 6, 2023 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

Restated Employment Agreement between the Company and Peter Ferola dated August 20, 2023, as amended

EXHIBIT 10.3 22nd CENTURY GROUP, INC. AMENDED AND RESTATED EMPLOYMENT AGREEMENT This AMENDED AND RESTATED EMPLOYMENT AGREEMENT (“Agreement”) is dated as of , 2023 (the “Effective Date”) between 22nd CENTURY GROUP, INC., a Nevada corporation (“Company”) and Peter Ferola (“Employee”). WHEREAS, the Company and the Employee are parties to that certain Employment Agreement dated September 19, 2022 (the

Certificate of Amendment to Restated Articles of Incorporation filed October 16, 2023

Exhibit 3.1 Filed in the Office of Secretary of State State Of Nevada Business Number E0607512005-3 Filing Number 20233560667 Filed On 10/16/2023 1:06:00 PM Number of Pages 2

Form of Securities Purchase Agreement, dated October 17, 2023, by and between 22nd Century Group, Inc. and each of the Purchasers (as defined therein).

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of October 17, 2023, between 22nd Century Group, Inc., a Nevada corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”). WHEREAS, subject to the terms and condition

4.8           Form of Placement Agent Warrant (Incorporated by reference from Exhibit 4.3 to the Company’s Form 8-K filed with the Commission on October 18, 2023).

Exhibit 4.3 PLACEMENT AGENT COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc. Warrant Shares: [] Initial Issuance Date: October 19, 2023 THIS PLACEMENT AGENT 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

Form of Pre-Funded Warrant.

Exhibit 4.2 PRE-FUNDED COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc. Warrant Shares: [] Initial Exercise Date: October 19, 2023 THIS PRE-FUNDED 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 afte

22nd Century Announces Pricing of $5.25 Million Public Offering

Exhibit 99.1 22nd Century Announces Pricing of $5.25 Million Public Offering BUFFALO, N.Y., October 17, 2023 (GLOBE NEWSWIRE) - 22nd Century Group, Inc. (Nasdaq: XXII) (the “Company”), a leading biotechnology company dedicated to improving health with reduced nicotine tobacco, hemp/cannabis and hops advanced plant technologies, today announced the pricing of its previously announced public offerin

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): October 17, 2023 22nd Century Gro

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): October 17, 2023 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

7,600,000 Shares of Common Stock Common Warrants to Purchase up to 20,000,000 Shares of Common Stock Pre-Funded Warrants to Purchase up to 2,400,000 Shares of Common Stock Placement Agent Warrants to Purchase up to 1,000,000 Shares of Common Stock Up

Prospectus Supplement (To Prospectus dated March 31, 2023) Filed Pursuant to Rule 424(b)(5) Registration No.

4.7           Form of Common Warrant (Incorporated by reference from Exhibit 4.1 to the Company’s Form 8-K filed with the Commission on October 18, 2023).

Exhibit 4.1 COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc. Warrant Shares: [] Initial Exercise Date: October 19, 2023 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 date hereof (the

Subject to completion, dated October 16, 2023

The information in this preliminary prospectus supplement is not complete and may be changed.

22nd Century Announces Proposed Public Offering

Exhibit 99.1 22nd Century Announces Proposed Public Offering BUFFALO, N.Y., October 16, 2023 (GLOBE NEWSWIRE) - 22nd Century Group, Inc. (Nasdaq: XXII) (the “Company”), a leading biotechnology company dedicated to improving health with reduced nicotine tobacco, hemp/cannabis and hops advanced plant technologies, today announced that it intends to offer and sell in a “best efforts” public offering

4.6           Waiver and Amendment Agreement (Incorporated by reference from Exhibit 10.1 to the Company’s Form 8-K filed with the Commission on October 16, 2023).

Exhibit 10.1 WAIVER AND AMENDMENT AGREEMENT This Wavier and Amendment Agreement (the “Agreement”), dated as of October 16, 2023, is made by and between (i) JGB Partners, LP (“JGB Partners”), JGB Capital, LP (“JGB Capital”) and JGB Capital Offshore Ltd. (“JGB Offshore” and collectively with JGB Partners and JGB Capital, the “Holders” and each a “Holder”), (ii) 22nd Century Group, Inc., a Nevada cor

Regulation FD Disclosure, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Submission of Matters to a Vote of Security Holders

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): October 16, 2023 22nd Century Group, Inc. (Exact Name of Registrant as Specified in Charter) Nevada 001-36338 98-0468420 (State or Other Jurisdiction of Incorporation) (Commission Fil

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6I(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

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 20, 2023 22nd Century Grou

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 20, 2023 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

As filed with the Securities and Exchange Commission on August 18, 2023.

As filed with the Securities and Exchange Commission on August 18, 2023. File No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 22nd CENTURY GROUP, INC. (Exact Name of Registrant as Specified in Its Charter) Nevada 98-0468420 (State or Other Jurisdiction of Incorporation or Organization) (I.R.S. Employer

Filing Fee Exhibit (filed herewith).

EXHIBIT 107 Calculation of Filing Fee Tables Form S-8 (Form Type) 22nd Century Group, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6I(2)) ☐ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to §240.

CAUTIONARY NOTE ON FORWARD-LOOKING STATEMENTS This presentation contains forward-looking statements concerning our business operations, and financial performance and conditions, as well as our plans, objectives, and expectations for our business oper

Exhibit 99.2 XXII SECOND QUARTER EARNINGS PRESENTATION August 14, 2023 CAUTIONARY NOTE ON FORWARD-LOOKING STATEMENTS This presentation contains forward-looking statements concerning our business operations, and financial performance and conditions, as well as our plans, objectives, and expectations for our business operations and financial performance and conditions that are subject to risks and u

22nd CENTURY GROUP, INC. CONDENSED CONSOLIDATED BALANCE SHEETS (amounts in thousands, except per-share data)

Exhibit 99.1 22nd Century Group (XXII) Reports Second Quarter 2023 Financial Results ● Second Quarter 2023 Net Revenues Increased 62% to $23.4 Million ● Launched VLN® Sales in California, Texas and Florida ● Delivered Record GVB Ingredient Volumes as Dominant Supplier in North America ● Initiated Operating Cost Reduction Program Targeting $15+ Million in Annualized Savings ● Updated 2023 Revenue O

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Quarterly Period Ended June 30, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period From to Commission File Number: 001-36338 22nd C

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 14, 2023 22nd Century Grou

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 14, 2023 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

Certificate of Amendment to Restated Articles of Incorporation filed June 16, 2023

Exhibit 3.1 #01,+ 03 7/, %-0*, 4- ',*5,7(5; 4- '7(7, '7(7, %- $,9(+( "8603,66 $82),5 /$*$+)%&$$)"' #0103. $82),5 &$&''&+%(,* #01,+ %3 *#%*#&$&' %&.%-.$$ 10 $82),5 4- &(.,6 &

Certificate of Change to Restated Articles of Incorporation filed June 30, 2023

Exhibit 3.2 #01,+ 03 7/, %-0*, 4- ',*5,7(5; 4- '7(7, '7(7, %- $,9(+( "8603,66 $82),5 /$*$+)%&$$)"' #0103. $82),5 &$&'''&%'(( #01,+ %3 *#'$#&$&' %$-$,-$$ .0 $82),5 4- &(.,6 %

22nd Century Announces Executive Leadership Changes Expands Board with New Highly Accomplished Independent Director Strengthens Balance Sheet and Implements $15 Million Cost Reduction Initiative

Exhibit 99.1 22nd Century Announces Executive Leadership Changes Expands Board with New Highly Accomplished Independent Director Strengthens Balance Sheet and Implements $15 Million Cost Reduction Initiative BUFFALO, N.Y., July 24, 2023 (GLOBE NEWSWIRE) – 22nd Century Group, Inc. (Nasdaq: XXII), a leading biotechnology company dedicated to improving health with reduced nicotine tobacco, hemp/canna

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): July 19, 2023 22nd Century Group,

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): July 19, 2023 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 N

Form of Securities Purchase Agreement, dated July 19, 2023, by and between 22nd Century Group, Inc. and each of the Purchasers (as defined therein).

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of July 19, 2023, between 22nd Century Group, Inc., a Nevada corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”). WHEREAS, subject to the terms and conditions s

Form of Warrant

Exhibit 4.1 EXHIBIT A COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc. Warrant Shares: Issue Date: [*], 2023 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 Issue Date (the “Initial Ex

4,373,219 Shares of Common Stock Warrants to Purchase 8,746,438 Shares of Common Stock

Prospectus Supplement (To Prospectus dated March 31, 2023) Filed Pursuant to Rule 424(b)(5) Registration No.

Form of Warrant

  Exhibit 4.1   COMMON STOCK PURCHASE WARRANT   22ND CENTURY GROUP, inc.   Warrant Shares:                                                 Issue Date: July 10, 2023   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