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person · Reporting owner

SICIGNANO HENRY III

Disclosed activity across 4 companies

Tapewire entity
10227
SEC CIK
0001508753

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
22nd Century Group, Inc.XXII · Entity 8519Director · President and CEOMarch 06, 2018April 03, 2018
Charlie's Holdings, Inc.CHUC · Entity 7095PresidentSeptember 03, 2026September 04, 2026
Greenwave Technology Solutions, Inc.GWAV · Entity 8288DirectorDecember 03, 2024December 04, 2024

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

22nd Century Group, Inc.

Report date March 06, 2018 · Filed April 03, 2018

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Stock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $2.76 · Expires 2028-03-06Direct279,553 Reported balance After 2018-03-06 transaction · row 5 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 5 · 2018-03-06 · Grant · Acquired 279,553 · Balance 279,553

F2: Stock option grant which vests one-third on March 6, 2019, March 6, 2020 and March 6, 2021.

Stock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $0.69 · Expires 2022-05-18Direct100,000 Reported balance Holding disclosure · report date 2018-03-06 · row 6 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 6 · Balance 100,000

Stock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $0.96 · Expires 2025-02-16Direct350,000 Reported balance Holding disclosure · report date 2018-03-06 · row 7 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 7 · Balance 350,000

Stock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $0.95 · Expires 2026-03-04Direct425,532 Reported balance Holding disclosure · report date 2018-03-06 · row 8 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 8 · Balance 425,532

F4: Stock option grant which vests one-third on each of March 4, 2017, March 4, 2018 and March 4, 2019.

Common StockSEC Table I · non-derivativeDirect2,509,422 Reported balance Holding disclosure · report date 2018-03-06 · row 1 Holding and transaction disclosures are not merged.
1 source row

Row 1 · Balance 2,509,422

Common StockSEC Table I · non-derivativeIndirectCustodian for Minor Child20,000 Reported balance Holding disclosure · report date 2018-03-06 · row 2 Holding and transaction disclosures are not merged.
1 source row

Row 2 · Balance 20,000

Common StockSEC Table I · non-derivativeIndirectIRA20,000 Reported balance Holding disclosure · report date 2018-03-06 · row 3 Holding and transaction disclosures are not merged.
1 source row

Row 3 · Balance 20,000

Common StockSEC Table I · non-derivativeIndirectManager2,542,347 Reported balance Holding disclosure · report date 2018-03-06 · row 4 Holding and transaction disclosures are not merged.
1 source row

Row 4 · Balance 2,542,347

F1: Shares are owned by Henry Sicignano III Group, LLC.

Sock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $1.39 · Expires 2027-05-24Direct333,000 Reported balance Holding disclosure · report date 2018-03-06 · row 9 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 9 · Balance 333,000

F3: Stock option grant which vests one-third on each of April 1, 2018, April 1, 2019 and April 1, 2020.

Filing footnotes · ownership attribution and instrument terms

F1: Shares are owned by Henry Sicignano III Group, LLC.

F2: Stock option grant which vests one-third on March 6, 2019, March 6, 2020 and March 6, 2021.

F3: Stock option grant which vests one-third on each of April 1, 2018, April 1, 2019 and April 1, 2020.

F4: Stock option grant which vests one-third on each of March 4, 2017, March 4, 2018 and March 4, 2019.

Charlie's Holdings, Inc.

Report date September 03, 2026 · Filed September 04, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect10,350,001 Reported balance After 2026-09-03 transaction · row 1
1 source row

Row 1 · 2026-09-03 · Grant · Acquired 500,000 · Balance 10,350,001

F1: Represents shares of restricted stock granted pursuant to the Issuer's 2019 Omnibus Equity Incentive Plan. The shares will vest in two equal annual installments on the first and second anniversaries of the grant, subject to continued service.

Common StockSEC Table I · non-derivativeIndirectIRA100,000 Reported balance Holding disclosure · report date 2026-09-03 · row 2 Holding and transaction disclosures are not merged.
1 source row

Row 2 · Balance 100,000

Filing footnotes · ownership attribution and instrument terms

F1: Represents shares of restricted stock granted pursuant to the Issuer's 2019 Omnibus Equity Incentive Plan. The shares will vest in two equal annual installments on the first and second anniversaries of the grant, subject to continued service.

Greenwave Technology Solutions, Inc.

Report date December 03, 2024 · Filed December 04, 2024

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common Stock, par value $0.001SEC Table I · non-derivativeDirect300,000 Reported balance After 2024-12-03 transaction · row 1
1 source row

Row 1 · 2024-12-03 · Grant · Acquired 300,000 · Balance 300,000

F1: Represents a Restricted Stock Award of 300,000 shares of common stock of Greenwave Technology Solutions, Inc. (the "Issuer") granted to the Reporting Person pursuant to the Issuer's 2024 Equity Incentive Plan, which such award vested at 100% immediately on December 3, 2024 and is not subject to forfeiture.

Common Stock, par value $0.001SEC Table I · non-derivativeIndirectBy IRA400,000 Reported balance After 2024-12-04 transaction · row 2 Account identity is unresolved; indirect or unspecified ownership is not merged.
1 source row

Row 2 · 2024-12-04 · Purchase · Acquired 100,000 · Balance 400,000

Filing footnotes · ownership attribution and instrument terms

F1: Represents a Restricted Stock Award of 300,000 shares of common stock of Greenwave Technology Solutions, Inc. (the "Issuer") granted to the Reporting Person pursuant to the Issuer's 2024 Equity Incentive Plan, which such award vested at 100% immediately on December 3, 2024 and is not subject to forfeiture.

Past disclosures · reporting ended (1)

No longer tracked through insider filings. These historical balances do not imply present ownership or a zero position.

Kartoon Studios, Inc.

Report date December 12, 2025 · Filed December 15, 2025

Section 16 reporting ended · disclosed 2025-12-15. Current position is not established by this disclosure.

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect170,366 Reported balance After 2025-12-12 transaction · row 1 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 1 · 2025-12-12 · Grant · Acquired 101,798 · Balance 170,366

F1: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Filing footnotes · ownership attribution and instrument terms

F1: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
September 03, 2026 Filed Sep 4, 2026 21:55 UTC Charlie's Holdings, Inc. CHUC · Entity 7095 GrantCommon Stock 500,000 $0.00 $0.00
Disclosure

SEC source: 0000897069-26-001772 · form4.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,350,001

F1 · shares: Represents shares of restricted stock granted pursuant to the Issuer's 2019 Omnibus Equity Incentive Plan. The shares will vest in two equal annual installments on the first and second anniversaries of the grant, subject to continued service.

Read SEC document
February 13, 2026 Filed Feb 13, 2026 22:30 UTC Charlie's Holdings, Inc. CHUC · Entity 7095 PurchaseCommon Stock 250,000 $0.20 $50,000.00
Disclosure

SEC source: 0000897069-26-000328 · form4.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,850,001

Read SEC document
December 17, 2025 Filed Dec 17, 2025 21:48 UTC Charlie's Holdings, Inc. CHUC · Entity 7095 PurchaseCommon Stock 100,000 $0.21 $21,000.00
Disclosure

SEC source: 0000897069-25-001814 · form4.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,600,001

Read SEC document
December 12, 2025 Filed Dec 15, 2025 13:14 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 101,798 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-056923 · wk-form4_1765822471.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 170,366

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Read SEC document
December 11, 2025 Filed Dec 12, 2025 11:52 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 6,452 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-056680 · wk-form4_1765558344.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,568

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Read SEC document
September 18, 2025 Filed Sep 23, 2025 11:54 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 6,097 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-042430 · wk-form4_1758642873.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 62,116

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Read SEC document
June 26, 2025 Filed Jun 30, 2025 12:31 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 6,805 $0.00 $0.00
Disclosure

SEC source: 0001355848-25-000077 · wk-form4_1751301077.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 56,019

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Read SEC document
April 11, 2025 Filed Apr 11, 2025 21:22 UTC Charlie's Holdings, Inc. CHUC · Entity 7095 GrantCommon Stock 500,000 $0.00 $0.00
Disclosure

SEC source: 0000897069-25-000794 · form4.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,500,001

F1 · shares: Represents shares of restricted stock granted pursuant to the Issuer's 2019 Omnibus Equity Incentive Plan. The shares will vest in two equal annual installments on the first and second anniversaries of the grant, subject to continued service.

Read SEC document
March 20, 2025 Filed Mar 21, 2025 16:49 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 8,228 $0.00 $0.00
Disclosure

SEC source: 0001355848-25-000034 · wk-form4_1742590178.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 49,214

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Read SEC document
January 03, 2025 Filed Jan 6, 2025 12:19 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 9,806 $0.00 $0.00
Disclosure

SEC source: 0001355848-25-000014 · wk-form4_1736183954.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,511

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Read SEC document
January 03, 2025 Filed Jan 7, 2025 18:47 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 8,475 $0.00 $0.00
Disclosure

SEC source: 0001355848-25-000024 · wk-form4_1736293661.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,986

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Read SEC document
December 04, 2024 Filed Dec 4, 2024 16:37 UTC Greenwave Technology Solutions, Inc. GWAV · Entity 8288 PurchaseCommon Stock, par value $0.001 100,000 $0.66 $65,900.00
Disclosure

SEC source: 0001493152-24-048675 · ownership.xml · nonDerivative · entry 2

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By IRA

Disclosed balance after: 400,000

Read SEC document
December 03, 2024 Filed Dec 4, 2024 16:37 UTC Greenwave Technology Solutions, Inc. GWAV · Entity 8288 GrantCommon Stock, par value $0.001 300,000 $0.00 $0.00
Disclosure

SEC source: 0001493152-24-048675 · ownership.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 300,000

F1 · shares: Represents a Restricted Stock Award of 300,000 shares of common stock of Greenwave Technology Solutions, Inc. (the "Issuer") granted to the Reporting Person pursuant to the Issuer's 2024 Equity Incentive Plan, which such award vested at 100% immediately on December 3, 2024 and is not subject to forfeiture.

Read SEC document
September 19, 2024 Filed Sep 23, 2024 13:01 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 5,814 $0.00 $0.00
Disclosure

SEC source: 0001355848-24-000134 · wk-form4_1727110862.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,705

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Read SEC document
March 21, 2024 Filed Mar 22, 2024 21:24 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 3,704 $0.00 $0.00
Disclosure

SEC source: 0001355848-24-000030 · wk-form4_1711157062.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,891

Read SEC document
January 09, 2024 Filed Jan 9, 2024 13:35 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 3,320 $0.00 $0.00
Disclosure

SEC source: 0001355848-24-000008 · wk-form4_1704825290.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 13,187

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "2023 Reverse Stock Split"). Upon effectiveness of the 2023 Reverse Stock Split, every 10 shares of voting common stock was automatically converted into 1 share of common stock.

Read SEC document
December 14, 2023 Filed Dec 18, 2023 18:17 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 3,497 $0.00 $0.00
Disclosure

SEC source: 0001683168-23-008930 · ownership.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,867

F1 · balance_after: On February 6, 2023, the issuer effected a 10-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "February 2023 Reverse Stock Split"). Upon effectiveness of the February 2023 Reverse Stock Split, every 10 shares of common stock was automatically converted into one share of common stock. On November 4, 2016, the issuer effected a 3-for-1 reverse stock split of the issued and outstanding shares of its common stock (the "November 2021 Reverse Stock Split"). Upon effectiveness of the November 2021 Reverse Stock Split, every 3 shares of common stock was automatically converted into one share of common stock.

Read SEC document
November 24, 2023 Filed Nov 24, 2023 21:54 UTC Charlie's Holdings, Inc. CHUC · Entity 7095 GrantCommon Stock 500,000 $0.00 $0.00
Disclosure

SEC source: 0000897069-23-001654 · form4.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,000,001

F1 · shares: Represents shares of restricted stock granted pursuant to the Issuer's 2019 Omnibus Equity Incentive Plan. The shares will vest in two equal annual installments on the first and second anniversaries of the grant, subject to continued service.

Read SEC document
September 14, 2023 Filed Sep 27, 2023 16:48 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 3,185 $0.00 $0.00
Disclosure

SEC source: 0001683168-23-006774 · ownership.xml · nonDerivative · entry 2

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,370

Read SEC document
July 18, 2023 Filed Sep 27, 2023 16:48 UTC Kartoon Studios, Inc. TOON · Entity 7329 GrantCommon Stock 3,185 $0.00 $0.00
Disclosure

SEC source: 0001683168-23-006774 · ownership.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,185

Read SEC document
January 04, 2023 Filed Jan 6, 2023 21:23 UTC Charlie's Holdings, Inc. CHUC · Entity 7095 GrantCommon Stock 500,000 $0.00 $0.00
Disclosure

SEC source: 0001567619-23-000641 · doc1.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · President

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,500,001

F1 · shares: Represents shares of restricted stock granted pursuant to the Issuer's 2019 Omnibus Equity Incentive Plan. The shares will vest in two equal annual installments on the first and second anniversaries of the grant, subject to continued service.

Read SEC document
November 29, 2022 Filed Nov 30, 2022 21:30 UTC Charlie's Holdings, Inc. CHUC · Entity 7095 PurchaseCommon Stock 100,000 $0.16 $16,370.00
Disclosure

SEC source: 0001567619-22-021053 · doc1.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · President

10b5-1 filing: Not disclosed

Ownership: Indirect · IRA

Disclosed balance after: 100,000

Read SEC document
March 02, 2022 Filed Mar 7, 2022 17:18 UTC Charlie's Holdings, Inc. CHUC · Entity 7095 GrantCommon Stock 500,000 $0.00 $0.00
Disclosure

SEC source: 0001415889-22-002628 · form4-03072022_090352.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · PRESIDENT

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,000,001

F1 · shares: Represents shares of restricted stock granted pursuant to the Issuer's 2019 Omnibus Equity Incentive Plan. The shares will no longer be subject to forfeiture in three equal annual installments, beginning on the first anniversary of the grant, subject to continued service.

Read SEC document
April 01, 2021 Filed May 13, 2021 22:10 UTC Charlie's Holdings, Inc. CHUC · Entity 7095 GrantCommon Stock 150,000,000 $0.00 $0.00
Disclosure

SEC source: 0001415889-21-002438 · form4-05132021_030536.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · PRESIDENT

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 750,000,002

F1 · shares: Represents shares of restricted stock granted in connection with the Reporting Person's appointment as President of the Issuer pursuant to the Issuer's 2019 Omnibus Equity Incentive Plan. 50% of the shares will no longer be subject to forfeiture on April 1, 2022, with the remainder being no longer subject to forfeiture on April 1, 2023, subject to continued employment.

Read SEC document
March 06, 2018 Filed Apr 3, 2018 17:05 UTC 22nd Century Group, Inc. XXII · Entity 8519 GrantStock Option (Right to Buy) · Derivative 279,553 $2.76 Strike: $2.76 $771,566.28
Disclosure

SEC source: 0001140361-18-016790 · doc1.xml · derivative · entry 5

SICIGNANO HENRY III · CIK 0001508753 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 279,553

Underlying: Common Stock · 279,553 shares

Expires 2028-03-06

F2 · derivative.exercise_date: Stock option grant which vests one-third on March 6, 2019, March 6, 2020 and March 6, 2021.

Read SEC document
June 09, 2017 Filed Jun 9, 2017 17:06 UTC 22nd Century Group, Inc. XXII · Entity 8519 OtherWarrant to Purchase · Derivative 300,000 $0.00 Strike: $0.60 $0.00
Disclosure

SEC source: 0001140361-17-024590 · doc1.xml · derivative · entry 6

SICIGNANO HENRY III · CIK 0001508753 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 300,000 shares

Expires 2017-11-09

Read SEC document
June 09, 2017 Filed Jun 9, 2017 17:06 UTC 22nd Century Group, Inc. XXII · Entity 8519 Tax withholdingCommon Stock 98,631 $1.83 $180,001.58
Disclosure

SEC source: 0001140361-17-024590 · doc1.xml · nonDerivative · entry 2

SICIGNANO HENRY III · CIK 0001508753 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,509,422

Read SEC document
June 09, 2017 Filed Jun 9, 2017 17:06 UTC 22nd Century Group, Inc. XXII · Entity 8519 OtherCommon Stock 300,000 $0.60 $180,000.00
Disclosure

SEC source: 0001140361-17-024590 · doc1.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,608,053

F1 · kind: Mr. Sicignano exercised warrant shares via a cashless exercise.

Read SEC document
May 24, 2017 Filed May 26, 2017 16:22 UTC 22nd Century Group, Inc. XXII · Entity 8519 GrantSock Option (Right to Buy) · Derivative 333,000 $1.39 Strike: $1.39 $462,870.00
Disclosure

SEC source: 0001140361-17-022548 · doc1.xml · derivative · entry 5

SICIGNANO HENRY III · CIK 0001508753 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 333,000

Underlying: Common Stock · 333,000 shares

Expires 2027-05-24

F2 · derivative.exercise_date: Stock option grant which vests one-third on each of April 1, 2018, April 1, 2019 and April 1, 2020.

Read SEC document
May 15, 2017 Filed May 16, 2017 16:41 UTC 22nd Century Group, Inc. XXII · Entity 8519 OtherWarrant to Purchase · Derivative 20,000 $0.60 Strike: $0.60 $12,000.00
Disclosure

SEC source: 0001140361-17-021010 · doc1.xml · derivative · entry 6

SICIGNANO HENRY III · CIK 0001508753 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 20,000 shares

Expires 2017-05-15

F1 · kind: Warrants exercised for cash.

Read SEC document
May 15, 2017 Filed May 16, 2017 16:41 UTC 22nd Century Group, Inc. XXII · Entity 8519 GiftCommon Stock 4,550 $0.00 $0.00
Disclosure

SEC source: 0001140361-17-021010 · doc1.xml · nonDerivative · entry 3

SICIGNANO HENRY III · CIK 0001508753 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Indirect · Custodian for Minor Child

Disclosed balance after: 20,000

Read SEC document
May 15, 2017 Filed May 16, 2017 16:41 UTC 22nd Century Group, Inc. XXII · Entity 8519 GiftCommon Stock 4,550 $0.00 $0.00
Disclosure

SEC source: 0001140361-17-021010 · doc1.xml · nonDerivative · entry 2

SICIGNANO HENRY III · CIK 0001508753 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,308,053

Read SEC document
May 15, 2017 Filed May 16, 2017 16:41 UTC 22nd Century Group, Inc. XXII · Entity 8519 OtherCommon Stock 20,000 $0.60 $12,000.00
Disclosure

SEC source: 0001140361-17-021010 · doc1.xml · nonDerivative · entry 1

SICIGNANO HENRY III · CIK 0001508753 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,312,603

F1 · kind: Warrants exercised for cash.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.