Major phytocannabinoid
Status changingTHCA-AΔ9-Tetrahydrocannabinolic acid A
(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-2-carboxylic acid
Aliases.THCA · Δ9-THCA-A · acide tétrahydrocannabinolique · delta-9-tetrahydrocannabinolic acid A
The natural acidic precursor of THC, non-intoxicating as long as it is not heated.
Updated on
Level of detail
Identifiers
- Formula
- C₂₂H₃₀O₄
- Molar mass
- 358.50 g·mol⁻¹
- CAS
- 23978-85-0
- PubChem CID
- 98523
- First described
- Isolé du cannabis dans les années 1960, l'acide Δ9-tétrahydrocannabinolique A est reconnu comme la forme acide native, non psychoactive, qui prédomine dans la plante fraîche avant tout chauffage.
- Origin
- A natural phytocannabinoid, the predominant acidic form of Δ9-THC present in unheated Cannabis sativa inflorescences.
- InChIKey
- UCONUSSAWGCZMV-HZPDHXFCSA-N
In plain terms
The natural acidic form of THC, as it exists in the fresh plant: with no intoxicating effect as long as it is not heated.
Receptors and activity
- CB1Ki ≈ 252 nM (McPartland et al., 2017) : affinité modeste, agoniste orthostérique faible et modulateur allostérique positifModulator
- CB2Ki ≈ 506 nM (McPartland et al., 2017)Inverse agonist
- PPARγAgonist
- 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
- Clarity30
- Sleep25
- Appetite40
- High15
Editorial estimate, not clinical.
Pharmacology
Δ9-Tetrahydrocannabinolic acid A is the natural acidic precursor of Δ9-THC: in the unheated plant it is this form that predominates, and it barely activates the CB1 receptors, hence its absence of psychotropic effect (Ki CB1 ≈ 252 nM, CB2 ≈ 506 nM; McPartland et al.). Preclinical research credits it above all with a PPARγ agonist action of anti-inflammatory and neuroprotective intent (Nadal et al., Palomares et al.). Heated, it decarboxylates and becomes active THC.
Key sources.
Biosynthetic pathway
In the plant, Δ9-tetrahydrocannabinolic acid A is formed by THCA synthase from cannabigerolic acid (CBGA), the common precursor of the major cannabinoids. Under the effect of heat or prolonged drying, it loses its acid function (decarboxylation) and converts into Δ9-THC.
Legal framework
France
An evolving and nuanced status. The ANSM decision of 22 May 2024 covers THC-type derivatives, and concentrated or isolated THCA is treated as a precursor of Δ9-THC: its presence is governed by the regulatory threshold of 0.3% total THC (after decarboxylation) set by the decree of 30 December 2021. A product whose THC content after conversion exceeds this threshold falls under the narcotics regime. Check the regulations in force before any purchase.
European Union
Governed under total THC in most Member States; hemp complying with the European THC thresholds remains authorised, but concentrated THCA extracts are the subject of increasing surveillance.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Major phytocannabinoid
- Origin
- A natural phytocannabinoid, the predominant acidic form of Δ9-THC present in unheated Cannabis sativa inflorescences.
- Status
- Status changing
Phytocannabinoïde de type dibenzopyrane (noyau benzo[c]chromène), portant une fonction acide carboxylique en position 2 : c'est cet acide qui distingue THCA-A du Δ9-THC.
Pharmacokinetics
La molécule est thermolabile : le chauffage (combustion, vaporisation, cuisson) la décarboxyle en Δ9-THC, si bien qu'une partie du THCA-A ingéré ou fumé est convertie en THC actif avant absorption.
Metabolism
Après décarboxylation en Δ9-THC, le devenir métabolique rejoint celui du THC (hydroxylation hépatique en 11-OH-THC puis oxydation en THC-COOH). Le THCA-A lui-même circule et peut être détecté sous forme intacte.
Detection and analysis
L'acide Δ9-tétrahydrocannabinolique A est un marqueur analytique de la consommation de cannabis peu chauffé ; il se distingue du Δ9-THC en chromatographie et sert de repère pour estimer la teneur totale en THC après décarboxylation.
References
- 1.McPartland et al. : Affinity and Efficacy Studies of THCA-A at CB1 and CB2 (PMC)
- 2.Palomares et al. : Δ9-THCA alleviates collagen-induced arthritis: role of PPARγ and CB1 (Br J Pharmacol)
- 3.ANSM : Décision du 22/05/2024 modifiant la liste des stupéfiants
- 4.PubChem CID 98523 : Δ9-Tetrahydrocannabinolic acid
Structured data
- InChIKey
- UCONUSSAWGCZMV-HZPDHXFCSA-N
- SMILES
- CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1C(=O)O)O
- Formula
- C22H30O4
- Molar mass
- 358.50 g·mol⁻¹
- CAS
- 23978-85-0
- PubChem CID
- 98523
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.