Major phytocannabinoid
Narcotic: generic clauseTHCVATetrahydrocannabivarinic acid
(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-2-carboxylic acid
Aliases.Acide tétrahydrocannabivarinique · THCV-A · Tetrahydrocannabivarinic acid · THCVA-A
The natural acid precursor of THCV, from the varinic series of cannabis.
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
- C₂₀H₂₆O₄
- Molar mass
- 330.40 g·mol⁻¹
- CAS
- 39986-26-0
- PubChem CID
- 59444416
- First described
- Identifié dans le cannabis comme forme acide native du THCV, isolé et caractérisé au fil des travaux sur les cannabinoïdes variniques.
- Origin
- A natural constituent of certain varieties of Cannabis sativa, in particular chemotypes rich in varinic cannabinoids.
- InChIKey
- IQSYWEWTWDEVNO-ZIAGYGMSSA-N
In plain terms
THCVA is the natural acid form of THCV, as found in the raw hemp plant before any heating.
Receptors and activity
- CB1Modulator
- CB2Modulator
- 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.
- Calm25
- Clarity30
- Sleep15
- Appetite18
- High15
Editorial estimate, not clinical.
Pharmacology
Tetrahydrocannabivarinic acid (THCVA) is the acid precursor of THCV, produced in cannabis from CBGVA by THCV synthase. In this acid form, it interacts only very weakly with the CB1 and CB2 receptors; it is its decarboxylation by heat or light that releases THCV, described in the literature as an antagonist at the CB1 receptor and a partial agonist at the CB2 receptor. It belongs to the varinic series, with a propyl chain.
Key sources.
- PubChem CID 59444416 : Tetrahydrocannabivarinic acid (identité, formule, InChIKey, IUPAC)
- Tetrahydrocannabivarin : Wikipedia (biosynthèse variniche, décarboxylation, pharmacologie du THCV)
- Pertwee et al. : CB1/CB2 receptor pharmacology of Δ9-THCV (partial agonist CB2, CB1 antagonism)PMID 17876302
- Décision ANSM du 22 mai 2024 modifiant la liste des substances classées comme stupéfiants (clause générique noyau benzo[c]chromène)
Biosynthetic pathway
In the plant, divarinolic acid condenses with geranyl pyrophosphate to form cannabigerovarinic acid (CBGVA), the common precursor of the varinic series. THCV synthase then cyclises CBGVA into tetrahydrocannabivarinic acid (THCVA). Under the effect of heat or light, THCVA decarboxylates into THCV.
Legal framework
International
Not documented
European Union
Constituant du cannabis, soumis aux cadres nationaux sur le THC et ses dérivés.
France
Encadré via la clause générique de la Décision ANSM du 22 mai 2024 (dérivés du noyau benzo[c]chromène) et le statut stupéfiant du cannabis.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Major phytocannabinoid
- Origin
- A natural constituent of certain varieties of Cannabis sativa, in particular chemotypes rich in varinic cannabinoids.
- Status
- Narcotic: generic clause
Cannabinoïde phytocannabinoïde de type THC (noyau tétrahydrobenzo[c]chromène, ou dibenzopyrane), sous sa forme acide carboxylique. Il appartient à la série varinique, caractérisée par une chaîne latérale propyle en C3 : deux carbones de moins que la chaîne pentyle des cannabinoïdes classiques.
Pharmacokinetics
Comme les autres cannabinoïdes acides, le THCVA est thermolabile : il se convertit en THCV lors du chauffage, ce qui conditionne fortement l'exposition réelle selon le mode de consommation.
Detection and analysis
En laboratoire, le THCVA se distingue du THCV par chromatographie (HPLC à froid) qui préserve la forme acide, alors que la chromatographie gazeuse, en chauffant l'échantillon, le décarboxyle en THCV.
References
- 1.PubChem CID 59444416 : Tetrahydrocannabivarinic acid (identité, formule, InChIKey, IUPAC)
- 2.Tetrahydrocannabivarin : Wikipedia (biosynthèse variniche, décarboxylation, pharmacologie du THCV)
- 3.Pertwee et al. : CB1/CB2 receptor pharmacology of Δ9-THCV (partial agonist CB2, CB1 antagonism)PMID 17876302
- 4.Décision ANSM du 22 mai 2024 modifiant la liste des substances classées comme stupéfiants (clause générique noyau benzo[c]chromène)
Structured data
- InChIKey
- IQSYWEWTWDEVNO-ZIAGYGMSSA-N
- SMILES
- CCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1C(=O)O)O
- Formula
- C20H26O4
- Molar mass
- 330.40 g·mol⁻¹
- CAS
- 39986-26-0
- PubChem CID
- 59444416
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.