Semi-synthetic cannabinoid
Narcotic: generic clause11-OH-Δ8-THC11-Hydroxy-Δ8-tetrahydrocannabinol
Aliases.11-OH-Δ8-THC · 11-hydroxy-delta-8-THC · 11-OH-delta8-THC · 11-hydroxy-Δ8-tétrahydrocannabinol
The active metabolite of delta-8-THC, the Δ8-series counterpart of 11-OH-THC, dominant by the oral route.
Updated on
Level of detail
Identifiers
- Formula
- C₂₁H₃₀O₃
- Molar mass
- 330.50 g·mol⁻¹
- CAS
- 28646-40-4
- PubChem CID
- 185651
- Origin
- No significant natural occurrence. The molecule forms in the body as a phase I metabolite of Δ8-THC, which is itself present only in trace amounts in cannabis and comes, in marketed products, from an isomerisation of cannabidiol carried out in the laboratory. It is also prepared as an analytical standard.
- InChIKey
- LOUSQMWLMDHRIK-IAGOWNOFSA-N
In plain terms
11-OH-Δ8-THC is what the liver makes from delta-8. As for classical THC, this metabolite stays active and becomes dominant when the product is swallowed rather than smoked, which explains the delayed potency of delta-8 edibles.
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.
- Calm50
- Clarity20
- Sleep55
- Appetite70
- High70
Editorial estimate, not clinical.
Pharmacology
11-hydroxy-Δ8-tetrahydrocannabinol is the main active metabolite of Δ8-THC, formed by hydroxylation of the methyl at position 11 under the action of hepatic cytochromes P450. It reproduces in the Δ8 series the role that 11-OH-Δ9-THC plays in the Δ9 series: a partial CB1 agonist, psychoactive, more potent than the molecule from which it derives, and produced in far greater proportion by the oral route owing to hepatic first pass. Its practical importance changed scale after 2019, with the commercial spread of Δ8-THC products obtained by acid isomerisation of hemp cannabidiol: the metabolite has become a common exposure marker in toxicology. That route of manufacture moreover poses a problem distinct from that of the metabolite itself, isomerisation of cannabidiol producing a mixture of isomers and by-products whose nature and quantity vary from lot to lot. 11-OH-Δ8-THC is then oxidised into 11-nor-9-carboxy-Δ8-THC acid, inactive, which serves as a urinary marker.
Route of preparation (chemical process)
There is no plant route for this molecule: it forms in the liver. Δ8-THC undergoes hydroxylation of the allylic methyl borne by carbon 11 under the action of cytochromes P450, a reaction analogous to the one that turns Δ9-THC into 11-OH-Δ9-THC. The double bond at position 8, more stable than the double bond at position 9, is not affected by that step.
Legal framework
France
As a hydroxylated derivative of tetrahydrocannabinol, 11-OH-Δ8-THC falls under the listing of THC and its derivatives in Annex IV of the arrêté of 22 February 1990. The Δ8-THC it comes from is itself treated as a narcotic in France, and no product containing it may be lawfully marketed. Its biological presence after exposure does not in itself constitute possession.
European Union
Tetrahydrocannabinol and its stereochemical variants appear in the schedules of the 1971 convention. Member States diverge on the treatment of isomers obtained by conversion of cannabidiol, several having adopted specific national measures after the rise of Δ8 products; the metabolite itself is lawfully produced only as a laboratory standard.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Semi-synthetic cannabinoid
- Origin
- No significant natural occurrence. The molecule forms in the body as a phase I metabolite of Δ8-THC, which is itself present only in trace amounts in cannabis and comes, in marketed products, from an isomerisation of cannabidiol carried out in the laboratory. It is also prepared as an analytical standard.
- Status
- Narcotic: generic clause
References
Structured data
- InChIKey
- LOUSQMWLMDHRIK-IAGOWNOFSA-N
- SMILES
- CCCCCC1=CC(=C2[C@@H]3CC(=CC[C@H]3C(OC2=C1)(C)C)CO)O
- Formula
- C21H30O3
- Molar mass
- 330.50 g·mol⁻¹
- CAS
- 28646-40-4
- PubChem CID
- 185651
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.