Semi-synthetic cannabinoid
Status changingHHCVHexahydrocannabivarin
(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
Aliases.hexahydrocannabivarin · HHCV · HHC-V · hexahydrocannabivarine
The propyl homologue of HHC, a mixture of epimers of variable composition, with no measured pharmacology.
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
- C₁₉H₂₈O₂
- Molar mass
- 288.40 g·mol⁻¹
- CAS
- -
- PubChem CID
- 175224406
- Origin
- A semi-synthetic compound, with no natural occurrence documented at a significant level. It is obtained by catalytic hydrogenation of a tetrahydrocannabivarin, itself arising from the cyclisation of cannabidivarin or of a related feedstock, on the model of the channel that produces HHC from hemp cannabidiol.
- InChIKey
- QYNCMPYNYFYQFE-JENMUQSASA-N
In plain terms
Hexahydrocannabivarin is a shortened version of hexahydrocannabinol, which appeared on the market when the latter was banned. It has been the subject of no study of its own: neither its potency, nor its effects, nor its safety are documented.
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.
- Calm30
- Clarity15
- Sleep30
- Appetite30
- High35
Editorial estimate, not clinical.
Pharmacology
Hexahydrocannabivarin is the propyl-chain homologue of hexahydrocannabinol, obtained by hydrogenation of the carbon ring of a tetrahydrocannabivarin. Its appearance illustrates a mechanism that has become routine on the semi-synthetic cannabinoid market: when a molecule is scheduled, its side-chain homologues are offered as substitutes, without any new data accompanying that displacement. An important structural caveat must be set out at once, and it holds for this whole family: hydrogenation creates a stereogenic centre at position 9 and produces a mixture of 9R and 9S epimers whose proportions vary from lot to lot, and which are not pharmacologically equivalent. For hexahydrocannabinol, the 9R epimer is a partial CB1 agonist comparable to Δ9-THC in nature but lesser in potency, while the 9S is markedly less active. What is bought under a single name is therefore in reality a mixture of variable composition. For hexahydrocannabivarin specifically, no affinity or efficacy has been measured, and the shortening of the side chain leads one to expect a potency lower still. No human data exist.
Route of preparation (chemical process)
No documented plant enzymatic route for this compound. It is obtained by hydrogenation of the double bond of the carbon ring of a tetrahydrocannabivarin, which turns the tetrahydro skeleton into a hexahydro skeleton. That saturation creates a stereogenic centre at position 9 and therefore generates two epimers. The molecule is described here by chemical class only.
Legal framework
France
The decision of the ANSM of 13 June 2023 placed hexahydrocannabinol and two of its derivatives, the acetate (HHC-O) and hexahydrocannabiphorol (HHCP), on the list of narcotics. Hexahydrocannabivarin is not named there. It does, however, fall under the generic clause targeting derivatives of the benzo[c]chromene core, introduced by the decision of the ANSM of 22 May 2024, its hexahydrobenzo[c]chromen-1-ol skeleton meeting that definition.
European Union
No harmonised control measure at Union level and no listing under the international conventions of 1961 and 1971. Hexahydrocannabinol has been monitored by the Union's early warning system since 21 October 2022, the first semi-synthetic cannabinoid to be so; chain homologues fall under national responses, heterogeneous from one Member State to another.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Semi-synthetic cannabinoid
- Origin
- A semi-synthetic compound, with no natural occurrence documented at a significant level. It is obtained by catalytic hydrogenation of a tetrahydrocannabivarin, itself arising from the cyclisation of cannabidivarin or of a related feedstock, on the model of the channel that produces HHC from hemp cannabidiol.
- Status
- Status changing
References
Structured data
- InChIKey
- QYNCMPYNYFYQFE-JENMUQSASA-N
- SMILES
- CCCc1cc2OC(C)(C)[C@@H]3CCC(C)C[C@H]3c2c(O)c1
- Formula
- C19H28O2
- Molar mass
- 288.40 g·mol⁻¹
- PubChem CID
- 175224406
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.