{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"YKKHSYLGQXKVMO-HZPDHXFCSA-N","prefName":"Δ8-tetrahydrocannabinolic acid","symbol":"Δ8-THCA","iupacName":"(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"],"cas":null,"pubchemCid":"59444391","chebiId":null,"smiles":"CCCCCC1=CC2=C([C@@H]3CC(=CC[C@H]3C(O2)(C)C)C)C(=C1C(=O)O)O","molecularFormula":"C22H30O4","molecularWeight":358.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/59444391"}},"classification":{"family":"mineur","familyLabel":"Minor phytocannabinoid","origin":"natural","originLabel":"Naturel","structuralClassFr":"Cannabinoïde acide de la série Δ8 : squelette benzo[c]chromène portant une fonction acide carboxylique en position 2, un phénol en position 1 et une chaîne pentyle en position 3, la double liaison occupant la position 8 du cycle carboné. Il se distingue de l'acide Δ9-tétrahydrocannabinolique A par la seule position de cette double liaison, interne au cycle et thermodynamiquement plus stable, ce qui vaut à toute la série Δ8 sa robustesse chimique et sa moindre puissance."},"originSynthesis":{"heading":"Biosynthetic pathway","summaryFr":"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.","originNote":"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.","discovered":"Le composé correspond à la forme acide du Δ8-tétrahydrocannabinol, sur le modèle de la relation qui unit l'acide Δ9-tétrahydrocannabinolique A au Δ9-THC. Son histoire est indissociable de celle du Δ8-THC lui-même, isolé du cannabis en 1966 mais à un rendement très faible : les cannabinoïdes de la série Δ8 ne sont présents dans la plante qu'à l'état de traces, et leur forme acide est d'autant plus rare. Sa présence naturelle robuste dans le chanvre n'est pas établie par la littérature consultée pour cette fiche, et il se rencontre surtout dans le contexte des préparations obtenues par isomérisation du cannabidiol."},"pharmacology":{"summaryFr":"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.","receptorSummaryFr":"Like the other acidic cannabinoids, it is devoid of intoxicating activity: the carboxylic acid function borne by the aromatic ring prevents efficient recognition by the CB1 receptor, in the same way as for Δ9-tetrahydrocannabinolic acid A, whose absence of psychoactive effect in humans is established. Activity appears after decarboxylation, which restores Δ8-THC, itself a partial CB1 agonist less potent than Δ9-THC. No affinity value specific to Δ8-THCA is published.","binding":[{"target":"CB1","efficacy":"partial_agonist","relativeActivity":4,"reported":null,"confidence":"low"},{"target":"CB2","efficacy":"partial_agonist","relativeActivity":4,"reported":null,"confidence":"low"}],"references":[{"label":"Chimie et pharmacologie du Δ8-tétrahydrocannabinol (revue, PMC 2024)","pmid":null,"doi":null,"url":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10976172/"},{"label":"Revue critique de l'acide Δ9-tétrahydrocannabinolique A (PMC 2017)","pmid":null,"doi":null,"url":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5549534/"},{"label":"PubChem CID 59444391 : acide Δ8-tétrahydrocannabinolique","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/59444391"}]},"pharmacokinetics":"Aucune donnée propre. Les cannabinoïdes acides sont plus polaires que leurs formes neutres et franchissent mal la barrière hématoencéphalique, ce qui contribue à leur absence d'effet psychotrope indépendamment de leur faible affinité pour le CB1. Toute exposition significative passe en pratique par la forme décarboxylée.","metabolism":"Aucune étude publiée pour ce composé. La décarboxylation, qui n'est pas une réaction métabolique mais une transformation chimique induite par la chaleur ou le temps, précède l'essentiel du devenir biologique : c'est le Δ8-THC formé qui est ensuite hydroxylé en position 11, puis oxydé en acide 11-nor-9-carboxy-Δ8-THC et glucuronidé.","detection":"Dosé en analyse de produits par chromatographie liquide, méthode qui préserve les formes acides, là où la chromatographie en phase gazeuse les décarboxyle dans l'injecteur et conduit à sous-estimer la teneur totale en l'absence de dérivation. Cette distinction méthodologique est essentielle pour l'interprétation des certificats d'analyse. En toxicologie humaine, le composé n'est pas un marqueur usuel.","subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":10},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":10},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":5},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":10},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":5}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":"Aucune donnée de toxicologie propre. Les préoccupations documentées portent sur les produits au Δ8-THC pris dans leur ensemble, dont les analyses révèlent des impuretés en concentrations très supérieures aux valeurs déclarées, et sur la hausse des signalements aux centres antipoison qui a accompagné leur diffusion. La forme acide n'est pas en elle-même identifiée comme un facteur de risque distinct."},"legal":{"scheduleStatus":"controlled-clause","scheduleLabel":"Narcotic: generic clause","frScheduleStatus":"controlled-clause","tiers":[{"jurisdiction":"international","jurisdictionLabel":"International","label":null,"reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"eu","jurisdictionLabel":"Union européenne","label":"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.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"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.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Chimie et pharmacologie du Δ8-tétrahydrocannabinol (revue, PMC 2024)","pmid":null,"doi":null,"url":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10976172/"},{"label":"Revue critique de l'acide Δ9-tétrahydrocannabinolique A (PMC 2017)","pmid":null,"doi":null,"url":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5549534/"},{"label":"PubChem CID 59444391 : acide Δ8-tétrahydrocannabinolique","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/59444391"}],"meta":{"slug":"delta-8-thca","url":"https://en.phytogrammes.com/wiki/delta-8-thca","lastVerified":"2026-05-01","dataUpdatedAt":"2026-08-14","confidence":"high","dataCompletenessPct":80,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}