Minor phytocannabinoid
Narcotic: generic clauseΔ8-THCAΔ8-tetrahydrocannabinolic acid
(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromene-2-carboxylic acid
Aliases.delta-8-THCA · Δ8-THCA-A · acide delta-8-tétrahydrocannabinolique · delta-8-tetrahydrocannabinolic acid
The non-intoxicating acid form of delta-8-THC, decarboxylated by heat; natural occurrence poorly established.
Updated on
Level of detail
Identifiers
- Formula
- C₂₂H₃₀O₄
- Molar mass
- 358.50 g·mol⁻¹
- CAS
- -
- PubChem CID
- 59444391
- Origin
- Marginal and poorly documented natural occurrence. The Δ8-THC from which it derives exists only in trace amounts in cannabis, almost all marketed Δ8-THC coming from an acid isomerisation of cannabidiol extracted from hemp. The acid form is consequently encountered above all as a minor constituent of plant samples or of preparations arising from that channel.
- InChIKey
- YKKHSYLGQXKVMO-HZPDHXFCSA-N
In plain terms
Δ8-THCA is the acid form of delta-8, the one that has not yet been heated. In that form the molecule produces no intoxicating effect: it is heat that, by removing its acid function, turns it into active delta-8.
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.
- Calm10
- Clarity10
- Sleep5
- Appetite10
- High5
Editorial estimate, not clinical.
Pharmacology
Δ8-tetrahydrocannabinolic acid is the carboxylated form of Δ8-THC, the counterpart in the Δ8 series of what Δ9-tetrahydrocannabinolic acid A is for Δ9-THC. Like all acidic cannabinoids it is not intoxicating: the acid function borne by the aromatic core prevents efficient activation of the CB1 receptor, and activity appears only after decarboxylation under the effect of heat, storage time or light. Its natural status calls for more caution than that of its Δ9 counterpart. Δ8-THC has been isolated from cannabis only at very low yield since 1966, and almost all Δ8-THC in circulation today comes from an acid isomerisation of hemp cannabidiol rather than from the plant; the robust natural presence of its acid form is not established by the literature consulted for this entry. The compound is therefore of interest above all for analysis: it enters into the calculation of total contents after conversion, and its presence alongside other by-products helps to characterise the origin of a sample. No pharmacological data of its own are published on it.
Biosynthetic pathway
In the plant, the acidic cannabinoids form through the action of synthases on cannabigerolic acid, Δ9-tetrahydrocannabinolic acid being the product of THCA synthase. No synthase dedicated to the Δ8 series is described: Δ8-THC is regarded as an isomerisation product of Δ9-THC, the double bond migrating to position 8, which is thermodynamically more stable. The corresponding acid form follows the same logic and has no established enzymatic route of its own.
Legal framework
France
Annex IV of the arrêté of 22 February 1990 classifies as narcotics the tetrahydrocannabinols, their esters, their ethers and their salts: Δ8-tetrahydrocannabinolic acid, which is a tetrahydrocannabinol bearing an acid function, falls under that heading, as does Δ9-tetrahydrocannabinolic acid. The practical question arises above all for product analyses, where the total content is calculated taking into account the decarboxylation of the acid forms.
European Union
Tetrahydrocannabinol and its stereochemical variants appear in the schedules of the convention of 1971. The treatment of acid forms varies between Member States, some including them in the calculation of the regulatory total THC level after conversion, others not; products arising from the isomerisation of cannabidiol are moreover the subject of specific national measures in several countries.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Minor phytocannabinoid
- Origin
- Marginal and poorly documented natural occurrence. The Δ8-THC from which it derives exists only in trace amounts in cannabis, almost all marketed Δ8-THC coming from an acid isomerisation of cannabidiol extracted from hemp. The acid form is consequently encountered above all as a minor constituent of plant samples or of preparations arising from that channel.
- Status
- Narcotic: generic clause
References
Structured data
- InChIKey
- YKKHSYLGQXKVMO-HZPDHXFCSA-N
- SMILES
- CCCCCC1=CC2=C([C@@H]3CC(=CC[C@H]3C(O2)(C)C)C)C(=C1C(=O)O)O
- Formula
- C22H30O4
- Molar mass
- 358.50 g·mol⁻¹
- PubChem CID
- 59444391
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.