22nd Century Group, Inc. — fact timeline

22nd Century Group, Inc. shareholders approved Ratification of WithumSmith+Brown, PC as independent registered public accountants for 2026 at the 2026-06-11 meeting.

“Proposal Three : To ratify the appointment of WithumSmith+Brown, PC as the Company’s independent registered public accountants for 2026.”

22nd Century Group, Inc. shareholders approved Advisory resolution approving executive compensation for fiscal year 2025 at the 2026-06-11 meeting.

“Proposal Two : To approve an advisory resolution approving executive compensation for fiscal year 2025.”

22nd Century Group, Inc. shareholders approved Election of Lucille Salhany as a Class III director at the 2026-06-11 meeting.

“Proposal One : To elect Lucille Salhany as a Class III director to serve until the 2029 annual meeting of the stockholders and until her respective successor has been elected and qualified.”

22nd Century Group, Inc.: Filing a Certificate of Amendment to effect a 1-for-20 reverse stock split of common stock (effective 2026-06-12).

“the Company will fill a Certificate of Amendment (the “ Certificate ”) pursuant to Nevada Revised Statutes (“ NRS ”) Section 78.209 with the Secretary of State of the State of Nevada authorizing a 1-for-20 reverse stock split of the Company’s issued and outstanding shares of common stock”

22nd Century Group, Inc. issued 1-for-20 reverse stock split of common stock.

“The Reverse Stock Split will become effective at 12:01 a.m. Eastern Time on June 12, 2026”

22nd Century Group, Inc. issued to purchase up to a number of shares of common stock equal to 100% of the number of shares of common stock issued pursuant to the exercise by the holders of the of warrant to holders of certain outstanding warrants.

“the Company agreed to issue new warrants (the “ Inducement Warrants ”) to purchase up to a number of shares of common stock equal to 100% of the number of shares of common stock issued pursuant to the exercise by the holders of the Existing Warrants, for cash, at a reduced exercise price equal to $0.4626.”

22nd Century Group, Inc. reported the first quarter ended March 31, 2026 results: revenue $4.1 million, net income $3.3 million.

“excluding discontinued operations related to the sale and exit of the Company’s hemp/cannabis business in late 2023, except as noted. ● Net revenues increased slightly to $4.1 million from $3.5 million. ● Gross profit (loss) improved to $(0.6) million, compared to $(0.8) million. ● Operating expenses were $2.4 million, increased from $2.0 million. ●”

22nd Century Group, Inc. entered into Sales Agreement with Needham & Company, LLC (effective 2026-05-01).

“On May 1, 2026, 22nd Century Group, Inc. (the “Company”) filed with the Securities and Exchange Commission a prospectus supplement to its Registration Statement on Form S-3 (Registration No. 333-294792) permitting the Company to sell $6,400,000 shares of the Company’s common stock pursuant to its sales agreement (as amended, the “Sales Agreement”) with Needham & Company, LLC.”

22nd Century Group, Inc. reported the quarter and full year ended December 31, 2025 results: revenue $3.5 million, net income Net loss was $2.8 million.

“excluding discontinued operations related to the sale and exit of the Company’s hemp/cannabis business in late 2023, except as noted. ● Net revenues decreased slightly to $3.5 million from $4.0 million. ● Gross profit (loss) improved to $(0.8) million, compared to $(1.1) million. ● Operating expenses were $2.0 million, decreased from $2.2 million. ●”

22nd Century Group, Inc.: Filed Certificate of Designation for Series B Convertible Preferred Stock, designating 20,000 shares with a stated value of $1,000 per share and setting forth terms including dividends, voting rights, conversion, redemption, liquidation preference, and negative covenants.

“The Company will file a Certificate of Designation of Preferences, Rights and Limitations with the Secretary of State of the State of Nevada designating 20,000 shares out of the authorized but unissued shares of its preferred stock as Series B Convertible Preferred Stock with a stated value of $1,000 per share (the “Series B Certificate of Designation”).”

22nd Century Group, Inc. entered into Securities Purchase Agreement with certain investors valued at up to $20 million (effective 2026-03-20).

“On March 20, 2026, 22nd Century Group, Inc. (the “Company”) and certain investors (the “Investors”) entered into a securities purchase agreement (the “Securities Purchase Agreement”) with respect to the offer and sale of up to $20 million of shares of Series B Convertible Preferred Stock, stated value $1,000 per share (the “Series B Preferred Stock”) and warrants (the “Warrants”) to purchase shares of common stock (“Common Stock”) pursuant to a registered direct offering (collectively, the “Offering”).”

22nd Century Group, Inc.: Filing of Certificate of Amendment to effect a 1-for-15 reverse stock split of common stock (effective 2026-01-26).

“On January 22, 2026, 22nd Century Group, Inc. (the “Company”) filed a Certificate of Amendment (the “Certificate”) pursuant to Nevada Revised Statutes (“NRS”) Section 78.209 with the Secretary of State of the State of Nevada authorizing a 1-for-15 reverse stock split of the Company’s issued and outstanding shares of common stock (the “Reverse Stock Split”).”

22nd Century Group, Inc. issued preferred stock.

“The matters described in Item 1.01 of this Current Report on Form 8-K related to the Preferred Stock and the Certificate of Amendment are incorporated herein by reference.”

22nd Century Group, Inc.: Certificate of Amendment of Certificate of Designations of Series A Convertible Preferred Stock filed.

“The Company will file a Certificate of Amendment of Certificate of Designations of Series A Convertible Preferred Stock ("Certificate of Amendment").”

22nd Century Group, Inc. engaged Withum Smith+Brown, PC as its auditor.

“on August 22, 2025, the Committee approved the engagement of Withum as the Company’s independent registered public accounting firm for the fiscal year ending December 31, 2025, effective immediately”

22nd Century Group, Inc. dismissed Freed Maxick P.C. as its auditor.

“On August 22, 2025, the Audit Committee (the “ Committee ”) of the Board of Directors (the “Board”) of 22 nd Century Group, Inc. (the “Company”) approved the replacement of Freed Maxick P.C. (“FM”) as the Company’s independent registered public accounting firm”

22nd Century Group, Inc.: Filing of Certificate of Designation for Series A Preferred Stock establishing rights, preferences, and limitations.

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

22nd Century Group, Inc.: Approved amendment to Articles of Incorporation to increase authorized common shares from 250 million to 500 million (effective 2025-07-15).

“the stockholders of the Company approved an amendment (the “Amendment”) to the Company’s Articles of Incorporation, as amended, to increase the number of authorized shares of common stock from two hundred fifty million (250,000,000) to five hundred million (500,000,000)”

22nd Century Group, Inc.: Certificate of Change filed to effect a 1-for-23 reverse stock split of common stock, reducing both authorized and outstanding shares proportionally (effective 2025-06-20).

“On June 16, 2025, 22nd Century Group, Inc. (the “Company”) filed a Certificate of Change (the “Certificate”) pursuant to Nevada Revised Statutes (“NRS”) Section 78.209 with the Secretary of State of the State of Nevada authorizing a 1-for-23 reverse stock split of the Company’s (a) authorized shares of common stock; and (b) issued and outstanding shares of common stock (the “Reverse Stock Split”).”

Anthony Johnson resigned as Director at 22nd Century Group, Inc..

“On May 22, 2025, Anthony Johnson, a Director of the Company, provided written notice to the Company that he is resigning effective July 15, 2025.”

22nd Century Group, Inc. received a nasdaq delisting notice notice regarding minimum bid price (rules 5810(c)(3)(A)(iii), 5550(a)(2)).

“December 16, 2024, the Company received a letter from Nasdaq notifying the Company that, as of December 13, 2024, the common stock had a closing bid price of $0.10 or less for 10 consecutive trading days. Accordingly, the Company is subject to the provisions of Listing Rule 5810(c)(3)(A)(iii) (the “Low Priced Stocks Rule”). As a result, Nasdaq has determined to delist the Company’s securities from The Nasdaq Capital Market, notwithstanding the Bid Price Cure Period, which is rendered unavailable by the Low Priced Stocks Rule. The Company has the right to appeal Nasdaq’s determination by Decemb”

22nd Century Group, Inc.: Amended articles of incorporation to effect a 1-for-135 reverse stock split (effective 2024-12-17).

“the Company filed a Certificate of Change (the “Certificate”) pursuant to Nevada Revised Statutes (“NRS”) Section 78.2055 with the Secretary of State of the State of Nevada authorizing a 1-for-135 reverse stock split of the Company’s issued and outstanding shares of common stock”

Robert Manfredonia was appointed as Executive Vice President of Sales and Marketing at 22nd Century Group, Inc..

“On July 30, 2024, the Company appointed Robert Manfredonia as its Executive Vice President of Sales and Marketing, effective August 1, 2024.”

John Miller departed as President of Tobacco at 22nd Century Group, Inc..

“On May 27, 2024, John Miller, the President of Tobacco for 22 nd Century Group, Inc. (the “Compay”), provided notice that he is resigning from such position effective August 2, 2024.”

22nd Century Group, Inc. reported the first quarter ended March 31, 2024 results: revenue $6.5 million.

“to $2.3 million, as compared to the prior comparative period of $17.5 million, and fourth quarter 2023 of $4.8 million. ● Net revenue from continuing operations was $6.5 million, as the Company further refined its revenue mix away from negative margin filtered cigars in favor of higher margin VLN ® and conventional cigarettes. ● Gross profit for the”

22nd Century Group, Inc. entered into General Release and Settlement Agreement with Omnia Capital LP valued at approximately $5.2 million (effective 2024-04-29).

“On April 29, 2024, 22nd Century Group, Inc. (the “Company”) entered into a General Release and Settlement Agreement (the “Agreement”) with Omnia Capital LP (“Omnia”).”

James Mish departed as Director at 22nd Century Group, Inc..

“On April 18, 2024, James Mish, a Director of the Company, provided written notice to the Company that he is resigning effective immediately.”

Nora B. Sullivan departed as Director at 22nd Century Group, Inc..

“On April 18, 2024, Nora B. Sullivan, a Director of 22 nd Century Group, Inc. (the “Company”), provided written notice to the Company that she is resigning effective immediately.”

22nd Century Group, Inc. entered into Securities Purchase Agreement with certain investors (the "Investors") valued at approximately $4.2 million (effective 2024-04-08).

“on April 8, 2024, the Company and certain investors (the “Investors”) entered into a securities purchase agreement (the “Securities Purchase Agreement”) relating to the issuance and sale of shares of common stock (or pre-funded warrants in lieu of common stock) pursuant to a registered direct offering and a private placement of warrants to purchase shares of common stock”

22nd Century Group, Inc. entered into Securities Purchase Agreement with certain investors (the “Investors”) valued at approximately $4.2 million (effective 2024-04-08).

“On April 8, 2024, the Company and certain investors (the “Investors”) entered into a securities purchase agreement (the “Securities Purchase Agreement”) relating to the issuance and sale of shares of common stock (or pre-funded warrants in lieu of common stock) pursuant to a registered direct offering and a private placement of warrants to purchase shares of common stock (collectively, the “Offering”).”

Jonathan Staffeldt was appointed as General Counsel at 22nd Century Group, Inc..

“On April 6, 2024, the Board of Directors also appointed Jonathan Staffeldt as the Company’s General Counsel effective immediately.”

Daniel Otto was appointed as Chief Financial Officer at 22nd Century Group, Inc..

“On April 6, 2024, the Board of Directors of the Company approved the appointment of Daniel Otto as its Chief Financial Officer, effective immediately.”

Hugh Kinsman resigned as Chief Financial Officer at 22nd Century Group, Inc..

“On April 6, 2024, Hugh Kinsman, the Company’s Chief Financial Officer, provided notice that he is resigning from such position effective June 1, 2024.”

22nd Century Group, Inc. received a nasdaq deficiency notice notice regarding stockholders equity (rules 5550(b)(1)).

“April 4, 2024, 22nd Century Group, Inc. (the “Company”) received a deficiency letter from the Nasdaq Listing Qualifications Department indicating that the Company was not in compliance with Nasdaq's Listing Rule 5550(b)(1) because the Company's shareholders' equity for the year ended December 31, 2023 (the "Year"), as reported in the Company's Form 10-K for the Year, was below the minimum shareholders' equity requirement of $2,500,000 (the "Shareholders' Equity Requirement"). The Notice had no immediate effect on the Company's continued listing on Nasdaq, subject to the Company's compliance wi”

22nd Century Group, Inc.: 1-for-16 reverse stock split via Certificate of Change (effective 2024-04-02).

“On March 28, 2024 22nd Century Group, Inc. (the “Company”) filed a Certificate of Change (the “Certificate”) pursuant to Nevada Revised Statutes (“NRS”) with the Secretary of State of the State of Nevada authorizing a 1-for-16 reverse stock split of the Company’s issued and outstanding shares of common stock”

22nd Century Group, Inc. reported the fourth quarter ended December 31, 2023 results: revenue $7.4 million, net income $22.1 million or $0.66 per share, EPS $0.66 per share.

“on recent business highlights. ​ Fourth quarter results and recent business activities included: ● Net revenue from continuing operations in the fourth quarter of 2023 was $7.4 million, ● Exited hemp/cannabis operations to fully focus on tobacco harm reduction and contract manufacturing activities, ● Substantially reduced operating costs through efficiency”

22nd Century Group, Inc.: Increased authorized shares of common stock from 66,666,667 to 250,000,000 (effective 2024-02-15).

“On February 15, 2024, the stockholders of the Company approved an amendment (the “Amendment”) to the Company’s Articles of Incorporation, as amended, to increase the number of authorized shares of common stock from sixty-six million, six hundred sixty-six thousand sixty hundred sixty-seven (66,666,667) to two hundred fifty million (250,000,000) which Amendment was filed and effective with the Secretary of the State of Nevada on February 15, 2024.”

22nd Century Group, Inc. shareholders approved To approve an amendment to the Company’s Articles of Incorporation to increase the number of authorized shares of common stock from 66,666,667 to 250,000,000 at the 2024-02-15 meeting.

“(1) To approve an amendment to the Company’s Articles of Incorporation to increase the number of authorized shares of common stock from sixty-six million, six hundred sixty-six thousand sixty hundred sixty-seven (66,666,667) to two hundred fifty million (250,000,000). In accordance with the voting results listed below, the proposal was approved. For Against Abstain Broker non-votes 21,999,112 7,351,104 198,805 0”

22nd Century Group, Inc. completed a disposition involving Specialty Acquisition Corporation for $3,100,000 (closed 2023-12-22).

“Company and the Buyer entered into an Amendment to Equity Purchase Agreement (the “ GVB Amendment ”) pursuant to which the Company and the Buyer increased the Purchase Price to $3,100,000 (the “ New Purchase Price ”) which consists of (i) a cash payment of $1,100,000 to the Company’s senior lender, on behalf of and at the direction of the Company and (ii) a 12%”

22nd Century Group, Inc. amended senior notes of cash payment of $2,200,000 to reduce the outstanding principal of the Debentures and a non-monetary exchange yielding fu with JGB Partners, LP, JGB Capital, LP, JGB Capital Offshore Ltd. (collectively, the Holders) and JGB Collateral, LLC (Agent) at 7% Original Issue Discount Senior Secured Debentures maturing the earlier of (i) June 30, 2024 and (ii) the public announcement of a Fundamental Transaction.

“the Purchase Agreement, as amended by the GVB Amendment. In consideration of the Holders and the Agents’ consent, the Company agreed to (i) pay to the Agent, a cash payment of $2,200,000 to reduce the outstanding principal of the Debentures (which includes the cash portion of the New Purchase Price paid directly to Agent by Buyer as described above), (ii)”

22nd Century Group, Inc. amended Amendment Agreement with JGB Partners, LP, JGB Capital, LP, JGB Capital Offshore Ltd. and JGB Collateral, LLC valued at $2,200,000 (effective 2023-12-22).

“On December 22, 2023, the Company, the Holders and the Agent entered into an Amendment Agreement (the “ JGB Amendment ”) pursuant to which the Holders and the Agent consented to the Purchase Agreement, as amended by the GVB Amendment.”

22nd Century Group, Inc. amended Amendment to Equity Purchase Agreement with Specialty Acquisition Corporation valued at $3,100,000 (effective 2023-12-22).

“On December 22, 2023, the Company and the Buyer entered into an Amendment to Equity Purchase Agreement (the “ GVB Amendment ”) pursuant to which the Company and the Buyer increased the Purchase Price to $3,100,000”

Peter Ferola was terminated as Chief Legal Officer and Corporate Secretary at 22nd Century Group, Inc..

“On December 21, 2023, Peter Ferola, the Chief Legal Officer and Corporate Secretary of 22nd Century Group, Inc., was terminated effective immediately.”

John Miller changed role as President of the Tobacco Business at 22nd Century Group, Inc..

“at which time, Mr. John Miller, the Company’s interim Chief Executive Officer, will resume the position of President of the Tobacco Business.”

Lawrence D. Firestone was appointed as Chairman of the Board and Chief Executive Officer at 22nd Century Group, Inc..

“On November 28, 2023, the Board appointed Lawrence D. Firestone as Chairman of the Board of Directors (“ Board ”), expanding the Board to eight directors, and as the Company’s Chief Executive Officer”

22nd Century Group, Inc. entered into Equity Purchase Agreement with Specialty Acquisition Corporation valued at $2,250,000 (effective 2023-11-20).

“On November 20, 2023, 22nd Century Group, Inc. (the “ Company ”) entered into an Equity Purchase Agreement (the “ Purchase Agreement ”) with Specialty Acquisition Corporation, a Nevada corporation (the “ Buyer ”) pursuant to which the Company agreed to sell substantially all of its GVB hemp/cannabis business (the “ Purchased Interests ”) for a purchase price of $2,250,000 (the “ Purchase Price ”).”

22nd Century Group, Inc. received a nasdaq noncompliance notice notice regarding minimum bid price (rules 5550(a)(2), 5810(c)(3)(A)).

“November 7, 2023, 22nd Century Group, Inc. (the “Company”) received a deficiency letter from the Nasdaq Listing Qualifications Department indicating that for the last 31 consecutive business days the Company’s common stock did not maintain a minimum closing bid price of $1.00 per share (the “Minimum Bid Price Requirement”) for continued listing on The Nasdaq Capital Market pursuant to Nasdaq Listing Rule 5550(a)(2). The notification of noncompliance has no immediate effect on the listing or trading of the Company’s common stock on the Nasdaq Capital Market. Under Nasdaq Listing Rule 5810(c)(3)”

22nd Century Group, Inc. entered into NCSU License Agreement with North Carolina State University valued at equal in value to $100,000 (effective 2023-11-02).

“On November 2, 2023, 22nd Century Group, Inc. (the “Company”) executed a licensing agreement (“NCSU License Agreement”) with North Carolina State University (“NCSU”).”

22nd Century Group, Inc. reported third quarter ended September 30, 2023 results: revenue $17.8 million.

“specific reference in such filing. ​ --- EX-99.1 (EX-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”