{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"LOUSQMWLMDHRIK-IAGOWNOFSA-N","prefName":"11-Hydroxy-Δ8-tetrahydrocannabinol","symbol":"11-OH-Δ8-THC","iupacName":null,"aliases":["11-OH-Δ8-THC","11-hydroxy-delta-8-THC","11-OH-delta8-THC","11-hydroxy-Δ8-tétrahydrocannabinol"],"cas":"28646-40-4","pubchemCid":"185651","chebiId":null,"smiles":"CCCCCC1=CC(=C2[C@@H]3CC(=CC[C@H]3C(OC2=C1)(C)C)CO)O","molecularFormula":"C21H30O3","molecularWeight":330.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/185651"}},"classification":{"family":"semisynthetique","familyLabel":"Semi-synthetic cannabinoid","origin":"semisynthetic","originLabel":"Semi-synthétique","structuralClassFr":"Dérivé hydroxylé du squelette benzo[c]chromène, isomère de position du 11-OH-Δ9-THC dont il ne diffère que par l'emplacement de la double liaison dans le cycle cyclohexène, en position 8 au lieu de 9. Cette double liaison interne est thermodynamiquement plus stable, ce qui explique la robustesse chimique de toute la série Δ8, et s'accompagne d'une puissance moindre sur le récepteur CB1."},"originSynthesis":{"heading":"Route of preparation (chemical process)","summaryFr":"There is no plant route for this molecule: it forms in the liver. Δ8-THC undergoes hydroxylation of the allylic methyl borne by carbon 11 under the action of cytochromes P450, a reaction analogous to the one that turns Δ9-THC into 11-OH-Δ9-THC. The double bond at position 8, more stable than the double bond at position 9, is not affected by that step.","originNote":"No significant natural occurrence. The molecule forms in the body as a phase I metabolite of Δ8-THC, which is itself present only in trace amounts in cannabis and comes, in marketed products, from an isomerisation of cannabidiol carried out in the laboratory. It is also prepared as an analytical standard.","discovered":"Décrit dans les travaux des années 1970 sur le métabolisme des isomères du tétrahydrocannabinol, à une époque où le Δ8-THC servait souvent de modèle expérimental du Δ9-THC en raison de sa plus grande stabilité chimique. Le composé a repris une actualité concrète après 2019, avec l'essor commercial des produits au Δ8-THC obtenus par isomérisation du cannabidiol issu du chanvre : il est devenu le métabolite actif de référence d'une consommation devenue massive."},"pharmacology":{"summaryFr":"11-hydroxy-Δ8-tetrahydrocannabinol is the main active metabolite of Δ8-THC, formed by hydroxylation of the methyl at position 11 under the action of hepatic cytochromes P450. It reproduces in the Δ8 series the role that 11-OH-Δ9-THC plays in the Δ9 series: a partial CB1 agonist, psychoactive, more potent than the molecule from which it derives, and produced in far greater proportion by the oral route owing to hepatic first pass. Its practical importance changed scale after 2019, with the commercial spread of Δ8-THC products obtained by acid isomerisation of hemp cannabidiol: the metabolite has become a common exposure marker in toxicology. That route of manufacture moreover poses a problem distinct from that of the metabolite itself, isomerisation of cannabidiol producing a mixture of isomers and by-products whose nature and quantity vary from lot to lot. 11-OH-Δ8-THC is then oxidised into 11-nor-9-carboxy-Δ8-THC acid, inactive, which serves as a urinary marker.","receptorSummaryFr":"A partial agonist of the CB1 receptor, psychoactive in animals. As for the Δ9 pair, hydroxylation at position 11 does not remove activity but preserves it, and the metabolite proves more potent than the Δ8-THC from which it derives. Δ8-THC and its metabolites remain broadly less potent than their counterparts in the Δ9 series, a difference attributed to the position of the double bond in the ring.","binding":[{"target":"CB1","efficacy":"partial_agonist","relativeActivity":75,"reported":null,"confidence":"low"},{"target":"CB2","efficacy":"partial_agonist","relativeActivity":60,"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":"PubChem CID 185651 : 11-hydroxy-Δ8-tétrahydrocannabinol","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/185651"}]},"pharmacokinetics":"La proportion de métabolite formée dépend de la voie d'administration, faible après inhalation et prépondérante après ingestion, comme pour la série Δ9. Aucune étude de pharmacocinétique humaine dédiée au 11-OH-Δ8-THC administré isolément n'est publiée : les données disponibles proviennent des profils métaboliques mesurés après consommation de Δ8-THC.","metabolism":"Formé par hydroxylation en C11 du Δ8-THC par les cytochromes P450 hépatiques, il est ensuite oxydé en acide 11-nor-9-carboxy-Δ8-THC, métabolite inactif et persistant, puis conjugué à l'acide glucuronique avant élimination urinaire et fécale. La séquence reproduit celle de la série Δ9, ce qui pose en toxicologie un problème de discrimination analytique entre les deux séries.","detection":"Recherché par chromatographie liquide couplée à la spectrométrie de masse en tandem. La difficulté centrale est la séparation d'avec les métabolites homologues de la série Δ9, isomères de position de masse identique : une méthode non optimisée peut faire passer une consommation de Δ8 pour une consommation de cannabis classique, ou l'inverse. Les immunoessais cannabis usuels présentent une réactivité croisée avec la série Δ8 sans permettre de distinguer les deux origines.","subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":50},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":20},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":55},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":70},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":70}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":"Le métabolite participe aux effets indésirables rapportés avec les produits au Δ8-THC ingérés : intensité inattendue, tachycardie, anxiété aiguë. Les signalements aux centres antipoison américains ont fortement augmenté avec la diffusion de ces produits, en particulier chez des personnes peu expérimentées et chez des enfants ayant ingéré des comestibles. Une part du risque tient aux sous-produits de l'isomérisation présents dans les produits finis, distincts du métabolite lui-même."},"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 1971 convention. Member States diverge on the treatment of isomers obtained by conversion of cannabidiol, several having adopted specific national measures after the rise of Δ8 products; the metabolite itself is lawfully produced only as a laboratory standard.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"As a hydroxylated derivative of tetrahydrocannabinol, 11-OH-Δ8-THC falls under the listing of THC and its derivatives in Annex IV of the arrêté of 22 February 1990. The Δ8-THC it comes from is itself treated as a narcotic in France, and no product containing it may be lawfully marketed. Its biological presence after exposure does not in itself constitute possession.","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":"PubChem CID 185651 : 11-hydroxy-Δ8-tétrahydrocannabinol","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/185651"}],"meta":{"slug":"11-oh-delta-8-thc","url":"https://en.phytogrammes.com/wiki/11-oh-delta-8-thc","lastVerified":"2026-05-01","dataUpdatedAt":"2026-08-14","confidence":"medium","dataCompletenessPct":80,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}