Semi-synthetic cannabinoid
Narcotic: generic clauseHHC-BHexahydrocannabutol
(6aR,10aR)-3-butyl-6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
Aliases.HHCB · HHC butyle · Hexahydrocannabutol
The hydrogenated butyl homologue of HHC, a presumed partial agonist of CB1.
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
- C₂₀H₃₀O₂
- Molar mass
- 302.50 g·mol⁻¹
- CAS
- -
- PubChem CID
- 175224409
- First described
- Molécule décrite dans la vague des homologues hydrogénés de synthèse commercialisés à partir de 2022-2023, dans le sillage de l'HHC.
- Origin
- A semi-synthetic hydrogenated derivative, obtained from tetrahydrocannabutol (THCB), itself the butyl homologue of THC.
- InChIKey
- UGRLMQVLYLFVDE-GNHXQJIDSA-N
In plain terms
HHC-B is a hydrogenated cousin of THC with a short (butyl) chain, obtained in the laboratory and still very little studied.
Receptors and activity
- CB1Partial agonist
- CB2Agonist
- 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
- Clarity20
- Sleep45
- Appetite50
- High62
Editorial estimate, not clinical.
Pharmacology
Hexahydrocannabutol (HHC-B) is a semi-synthetic cannabinoid of the HHC family, from which it is distinguished by a butyl (four-carbon) side chain instead of the usual pentyl chain. Like HHC and THC, it has the hydrogenated dibenzopyran skeleton and would act as a partial agonist of the CB1 receptor, the mechanism behind its psychoactive effects. The available studies concern chiefly HHC and HHC-P; the parameters specific to HHC-B remain extrapolated and uncharacterised in humans.
Key sources.
- In vitro activation of the CB1 receptor by the semi-synthetic cannabinoids HHC, HHC-O and HHC-P (PMC)PMID PMC11994375
- Isolation of Δ9-Tetrahydrocannabutol, the butyl homologue of Δ9-THC (J. Nat. Prod.)DOI 10.1021/acs.jnatprod.9b00876
- ANSM : décision du 22/05/2024 classant l'HHC et ses dérivés comme stupéfiants
- PubChem CID 175224409 : Hexahydrocannabutol
Route of preparation (chemical process)
Route of obtention: HHC-B does not come from a direct plant biosynthesis but from a two-stage chemical transformation. One starts from cannabidiol (CBD) derived from hemp, converted by cyclisation into a dibenzopyran-type cannabinoid with a butyl chain (THCB), whose terpene ring double bond is then saturated by catalytic hydrogenation. This reduction removes the point of unsaturation and gives the hexahydrogenated skeleton characteristic of the HHC family, here bearing a four-carbon side chain.
Legal framework
France
In France, hydrogenated derivatives sharing the benzo[c]chromene core of THC fall under the generic clause of the ANSM decision of 22 May 2024 classifying HHC and its derivatives as narcotics; HHC-B, the hydrogenated homologue of that same family, falls under this regime. Production, sale and consumption are prohibited.
European Union
Status varies across Member States; several countries have banned HHC and its homologues, and these molecules are monitored by the European drugs agency (EUDA/EMCDDA). To be regarded as not authorised for consumption in most jurisdictions.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Semi-synthetic cannabinoid
- Origin
- A semi-synthetic hydrogenated derivative, obtained from tetrahydrocannabutol (THCB), itself the butyl homologue of THC.
- Status
- Narcotic: generic clause
Cannabinoïde hydrogéné de type dibenzopyrane (benzo[c]chromène), homologue à chaîne latérale butyle (C4) de l'hexahydrocannabinol.
Pharmacokinetics
Par analogie avec l'HHC, une administration par inhalation ou voie orale est attendue, avec un métabolisme hépatique de type cannabinoïde. Aucune donnée pharmacocinétique humaine spécifique à l'HHC-B n'est publiée à ce jour.
Toxicology and risks
Aucune étude toxicologique humaine à long terme n'existe pour l'HHC-B ; le profil de risque est extrapolé de l'HHC, avec lequel l'ANSM associe un risque d'abus et de dépendance comparable au cannabis, ainsi que des effets aigus rapportés (anxiété, tachycardie, confusion).
References
- 1.In vitro activation of the CB1 receptor by the semi-synthetic cannabinoids HHC, HHC-O and HHC-P (PMC)PMID PMC11994375
- 2.Isolation of Δ9-Tetrahydrocannabutol, the butyl homologue of Δ9-THC (J. Nat. Prod.)DOI 10.1021/acs.jnatprod.9b00876
- 3.ANSM : décision du 22/05/2024 classant l'HHC et ses dérivés comme stupéfiants
- 4.PubChem CID 175224409 : Hexahydrocannabutol
Structured data
- InChIKey
- UGRLMQVLYLFVDE-GNHXQJIDSA-N
- SMILES
- CCCCC1=CC(=C2[C@@H]3CC(CC[C@H]3C(OC2=C1)(C)C)C)O
- Formula
- C20H30O2
- Molar mass
- 302.50 g·mol⁻¹
- PubChem CID
- 175224409
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.