Semi-synthetic cannabinoid
Narcotic: generic clauseTHC-OTHC-O-acetate (Δ9-tetrahydrocannabinol acetate)
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl acetate
Aliases.THC-O-A · THC acetate · ATHC
A THC prodrug sold as "THC-O". "EVALI"-like pulmonary toxicity documented in 2021.
Updated on
Level of detail
Harm-reduction warning
No characterised human dose: animal / in vitro data only. Effect profile, safety margin and acute toxicity are not documented in human clinical practice. Extremely potent compound: severe effects, seizures and deaths reported in the literature.
Identifiers
- Formula
- C₂₃H₃₂O₃
- Molar mass
- 356.50 g·mol⁻¹
- CAS
- 23132-17-4
- PubChem CID
- 198013
- First described
- 1949
- Origin
- Semi-synthesis (acetylation of THC)
- InChIKey
- DEWSJDIJFWQLOA-RTBURBONSA-N
In plain terms
THC-O-acetate is a modified version of THC sold in some American vape shops. Several cases of severe lung injury have been documented (close to the EVALI syndrome of 2019-2020). Best avoided.
Receptors and activity
- CB1via hydrolyse → THCPartial agonist
- CB2Partial agonist
- Agonist
- Partial agonist
- Antagonist
- Modulator
- Inverse agonist
Hover over a row for the precise value (Ki, EC50…)
Subjective signature
Hover over an axis to read its definition.
- Calm50
- Clarity25
- Sleep75
- Appetite80
- High90
Editorial estimate, not clinical.
Pharmacology
THC-O-acetate (Adams, JACS 1949) is the acetate ester of Δ9-THC on the phenolic hydroxyl. A prodrug: it is hydrolysed to active THC after inhalation or ingestion, which explains the delayed onset (≈ 30-45 min) and the subjectively "stronger" effect (~ 3× THC according to users). Critical point: when vaped, the compound undergoes partial pyrolysis producing **ketene** (OC=CH₂) - a powerfully lung-irritant gas associated with the EVALI syndrome (Munger et al., Chem Res Toxicol 2023, PMID 37449873). France: captured by the **ANSM Decision of 22 May 2024** (benzo[c]chromene clause).
Key sources.
Route of preparation (chemical process)
Acetylation of the phenolic hydroxyl of Δ9-THC (acetic anhydride in pyridine) - a prodrug (THC is released by hepatic hydrolysis)
Legal framework
International
Couvert comme isomère du THC
1971 Sched II
European Union
Régime cannabis dans la plupart des États
France
Stupéfiant : clause benzo[c]chromène
Décision ANSM 22 mai 2024
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Semi-synthetic cannabinoid
- Origin
- Semi-synthesis (acetylation of THC)
- Status
- Narcotic: generic clause
References
- 1.Munger · Chem Res Toxicol 2023PMID 37449873
Structured data
- InChIKey
- DEWSJDIJFWQLOA-RTBURBONSA-N
- SMILES
- CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)OC(=O)C
- Formula
- C23H32O3
- Molar mass
- 356.50 g·mol⁻¹
- CAS
- 23132-17-4
- PubChem CID
- 198013
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.