Semi-synthetic cannabinoid
Unschedulediso-THCIsotetrahydrocannabinol
(1R,12R)-9-methyl-5-pentyl-12-prop-1-en-2-yl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6-trien-3-ol
Aliases.isotetrahydrocannabinol · iso-THC · Δ8-iso-THC · isotétrahydrocannabinol
A by-product of the acid cyclisation of cannabidiol, with a non-cannabinoid skeleton and undocumented pharmacology.
Updated on
Level of detail
Identifiers
- Formula
- C₂₁H₃₀O₂
- Molar mass
- 314.50 g·mol⁻¹
- CAS
- -
- PubChem CID
- 176804934
- Origin
- A conversion compound, formed during the acid cyclisation of cannabidiol. It is not described as a notable natural constituent of hemp: it is encountered above all as a by-product in preparations obtained by isomerisation of cannabidiol, a channel that has become massive since cannabidiol-rich hemp began to be produced in surplus.
- InChIKey
- NUXUDGMVYZUFNQ-NXRUOVBSSA-N
In plain terms
Isotetrahydrocannabinol forms when cannabidiol is chemically turned into THC and the reaction goes in a different direction from the one intended. It is a manufacturing by-product, very little studied, whose effects are unknown.
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.
- Calm5
- Clarity5
- Sleep5
- Appetite5
- High5
Editorial estimate, not clinical.
Pharmacology
Isotetrahydrocannabinol denotes a family of isomers arising from the intramolecular cyclisation of cannabidiol in acid medium, a reaction used industrially to convert hemp cannabidiol into Δ8-THC or Δ9-THC. Kiselak and colleagues (2020) showed that the nature of the product depends on which double bond is attacked: activation of the Δ8 double bond gives the expected tetrahydrocannabinols, that of the Δ1 double bond leads to the iso-THC skeleton, a minority route. The result is not a tetrahydrocannabinol in the structural sense: the characteristic benzo[c]chromene ring is replaced by a bridged oxatricyclic system, and the molecule thus falls outside the template to which cannabinoid receptors respond. No affinity or activity data have been published for this compound, and this entry refrains from assuming any. Its practical interest lies elsewhere: the iso-THC isomers are among the by-products that acid isomerisation leaves in preparations, alongside other impurities, and their presence serves as a marker of the process used.
Route of preparation (chemical process)
No known plant enzymatic route for this isomer. It forms by intramolecular cyclisation of cannabidiol in acid medium: addition of the phenol onto one of the two double bonds of cannabidiol determines the skeleton obtained, and attack of the Δ1 double bond leads to the iso-THC framework instead of the benzo[c]chromene of THC. The molecule is described here by chemical class only.
Legal framework
France
The substance is named in no French text. Annex IV of the arrêté of 22 February 1990 classifies as narcotics the tetrahydrocannabinols, their esters, their ethers and their salts: isotetrahydrocannabinol, whose bridged oxatricyclic skeleton is not that of a tetrahydrocannabinol, does not fall directly under that heading. Its presence as an impurity in a product arising from the isomerisation of cannabidiol nonetheless leaves that product subject to the law applicable to its main constituent.
European Union
No harmonised control at Union level and no listing under the international conventions of 1961 and 1971. The molecule is treated above all as an analytical marker of cannabidiol isomerisation processes, a question belonging to product safety more than to narcotics law.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Semi-synthetic cannabinoid
- Origin
- A conversion compound, formed during the acid cyclisation of cannabidiol. It is not described as a notable natural constituent of hemp: it is encountered above all as a by-product in preparations obtained by isomerisation of cannabidiol, a channel that has become massive since cannabidiol-rich hemp began to be produced in surplus.
- Status
- Unscheduled
References
Structured data
- InChIKey
- NUXUDGMVYZUFNQ-NXRUOVBSSA-N
- SMILES
- CCCCCC1=CC(=C2[C@@H]3CC(CC[C@H]3C(=C)C)(OC2=C1)C)O
- Formula
- C21H30O2
- Molar mass
- 314.50 g·mol⁻¹
- PubChem CID
- 176804934
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.