Semi-synthetic cannabinoid
Narcotic: generic clause11-OH-THC11-Hydroxy-Δ9-tetrahydrocannabinol
(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-methanol
Aliases.11-OH-THC · 11-hydroxy-THC · 11-OH-Δ9-THC · 11-hydroxy-Δ9-tétrahydrocannabinol · 7-OH-THC
The major active metabolite of THC formed by the liver; it explains the delayed potency of edibles.
Updated on
Level of detail
Identifiers
- Formula
- C₂₁H₃₀O₃
- Molar mass
- 330.50 g·mol⁻¹
- CAS
- 36557-05-8
- PubChem CID
- 644022
- Origin
- No natural occurrence in the cannabis plant or in its extracts. The molecule forms in the body, as a phase I metabolite of Δ9-THC, and it is also prepared in the laboratory as an analytical standard. Its endogenous production is massively favoured by the oral route, where hepatic first pass transforms a large fraction of the ingested THC.
- InChIKey
- YCBKSSAWEUDACY-IAGOWNOFSA-N
In plain terms
11-OH-THC is what the liver makes from THC. It is what explains why an edible acts later but more strongly than a joint: having passed through the liver, THC is turned into a molecule at least as active as itself, which reaches the brain in its turn.
Receptors and activity
- CB1Partial 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.
- Calm45
- Clarity15
- Sleep60
- Appetite80
- High85
Editorial estimate, not clinical.
Pharmacology
11-hydroxy-Δ9-tetrahydrocannabinol is the main active metabolite of Δ9-THC, and the pharmacological key to the difference between inhaled and ingested cannabis. Formed by hydroxylation of the methyl at position 11 under the action of CYP2C9, it is produced in far greater quantity by the oral route, where hepatic and intestinal first pass processes the whole dose before its distribution. A partial CB1 agonist of affinity at least equal to that of THC, it is more potent than THC on several animal measures. Lemberger and colleagues (1973) administered 1 mg of it intravenously to nine occasional users: tachycardia and intoxicating effect appeared within three to five minutes, against ten to twenty minutes for Δ9-THC under the same conditions, and the intensity felt followed the plasma concentrations of the unchanged metabolite. Its own metabolism then involves CYP3A, CYP2C9 and glucuronidation by UGT2B7, before oxidation into 11-nor-9-carboxy-THC acid, inactive but very persistent, which is the target of urinary screening tests.
Route of preparation (chemical process)
There is no plant route for this molecule: it forms in the liver and the intestine. Δ9-THC undergoes hydroxylation of the allylic methyl borne by carbon 11, a reaction carried mainly by CYP2C9. That step is the first of the oxidative metabolism of THC, before the later oxidation into the 11-nor-9-carboxylic acid, itself inactive.
Legal framework
France
11-OH-THC is first of all a metabolite formed in the body of anyone exposed to THC: its biological presence does not in itself constitute possession. As a hydroxylated derivative of tetrahydrocannabinol, it falls under the listing of THC and its derivatives in Annex IV of the arrêté of 22 February 1990 as soon as it is isolated, produced or transferred as a substance. It enters into the composition of no product that can be lawfully marketed in France.
European Union
Tetrahydrocannabinol and its stereochemical variants appear in the schedules of the 1971 convention on psychotropic substances, whose application Member States ensure. No marketing authorisation covers 11-OH-THC as an active substance; it is lawfully produced only as a reference standard for toxicology laboratories.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Semi-synthetic cannabinoid
- Origin
- No natural occurrence in the cannabis plant or in its extracts. The molecule forms in the body, as a phase I metabolite of Δ9-THC, and it is also prepared in the laboratory as an analytical standard. Its endogenous production is massively favoured by the oral route, where hepatic first pass transforms a large fraction of the ingested THC.
- Status
- Narcotic: generic clause
References
Structured data
- InChIKey
- YCBKSSAWEUDACY-IAGOWNOFSA-N
- SMILES
- CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)CO)C(=C1)O
- Formula
- C21H30O3
- Molar mass
- 330.50 g·mol⁻¹
- CAS
- 36557-05-8
- PubChem CID
- 644022
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.