{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"YCBKSSAWEUDACY-IAGOWNOFSA-N","prefName":"11-Hydroxy-Δ9-tetrahydrocannabinol","symbol":"11-OH-THC","iupacName":"(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-methanol","aliases":["11-OH-THC","11-hydroxy-THC","11-OH-Δ9-THC","11-hydroxy-Δ9-tétrahydrocannabinol","7-OH-THC"],"cas":"36557-05-8","pubchemCid":"644022","chebiId":null,"smiles":"CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)CO)C(=C1)O","molecularFormula":"C21H30O3","molecularWeight":330.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/644022"}},"classification":{"family":"semisynthetique","familyLabel":"Semi-synthetic cannabinoid","origin":"semisynthetic","originLabel":"Semi-synthétique","structuralClassFr":"Dérivé hydroxylé du squelette benzo[c]chromène du Δ9-THC. La modification porte sur le méthyle allylique en position 11, transformé en alcool primaire, le reste du squelette et la stéréochimie 6aR,10aR restant inchangés. Cette hydroxylation augmente légèrement la polarité sans compromettre le passage de la barrière hématoencéphalique, ce qui distingue le 11-OH-THC de son successeur métabolique, l'acide carboxylique correspondant, trop polaire pour être actif dans le cerveau."},"originSynthesis":{"heading":"Route of preparation (chemical process)","summaryFr":"There is no plant route for this molecule: it forms in the liver and the intestine. Δ9-THC undergoes hydroxylation of the allylic methyl borne by carbon 11, a reaction carried mainly by CYP2C9. That step is the first of the oxidative metabolism of THC, before the later oxidation into the 11-nor-9-carboxylic acid, itself inactive.","originNote":"No natural occurrence in the cannabis plant or in its extracts. The molecule forms in the body, as a phase I metabolite of Δ9-THC, and it is also prepared in the laboratory as an analytical standard. Its endogenous production is massively favoured by the oral route, where hepatic first pass transforms a large fraction of the ingested THC.","discovered":"La molécule apparaît au début des années 1970, quand les travaux sur le métabolisme humain du cannabis cherchent à comprendre pourquoi l'effet du Δ9-THC ingéré diffère de celui du Δ9-THC fumé. Lemberger et collaborateurs en donnent la démonstration décisive en 1973 : administré par voie intraveineuse à neuf consommateurs occasionnels, le 11-OH-Δ9-THC produit en trois à cinq minutes une tachycardie marquée et un effet psychotrope, alors que le pic du Δ9-THC administré dans les mêmes conditions est retardé de dix à vingt minutes. Le métabolite n'est donc pas un produit de dégradation inerte, mais un porteur d'effet à part entière."},"pharmacology":{"summaryFr":"11-hydroxy-Δ9-tetrahydrocannabinol is the main active metabolite of Δ9-THC, and the pharmacological key to the difference between inhaled and ingested cannabis. Formed by hydroxylation of the methyl at position 11 under the action of CYP2C9, it is produced in far greater quantity by the oral route, where hepatic and intestinal first pass processes the whole dose before its distribution. A partial CB1 agonist of affinity at least equal to that of THC, it is more potent than THC on several animal measures. Lemberger and colleagues (1973) administered 1 mg of it intravenously to nine occasional users: tachycardia and intoxicating effect appeared within three to five minutes, against ten to twenty minutes for Δ9-THC under the same conditions, and the intensity felt followed the plasma concentrations of the unchanged metabolite. Its own metabolism then involves CYP3A, CYP2C9 and glucuronidation by UGT2B7, before oxidation into 11-nor-9-carboxy-THC acid, inactive but very persistent, which is the target of urinary screening tests.","receptorSummaryFr":"A partial agonist of the CB1 receptor, of affinity at least equal to that of Δ9-THC. In animals it proves more potent than the parent molecule on several measures, notably antinociception and drug discrimination. In humans, the demonstration by Lemberger and colleagues establishes a close correlation between the intensity of the intoxicating effect felt and the plasma concentrations of the unchanged metabolite.","binding":[{"target":"CB1","efficacy":"partial_agonist","relativeActivity":85,"reported":null,"confidence":"low"},{"target":"CB2","efficacy":"partial_agonist","relativeActivity":70,"reported":null,"confidence":"low"}],"references":[{"label":"Lemberger et coll. 1973 : pharmacologie comparée du Δ9-THC et du 11-OH-Δ9-THC chez l'humain","pmid":"4729039","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/4729039/"},{"label":"Lemberger et coll. 1972 : pharmacologie, disposition et métabolisme du 11-hydroxy-THC","pmid":"5041775","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/5041775/"},{"label":"Kumar et coll. 2022 : métabolisme extrahépatique du THC et du 11-OH-THC","pmid":"35370140","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/35370140/"}]},"pharmacokinetics":"La proportion de 11-OH-THC formée dépend fortement de la voie d'administration : faible après inhalation, elle devient comparable voire supérieure à celle du THC lui-même après ingestion, du fait du premier passage. Après administration intraveineuse de 1 mg chez l'humain, l'effet psychotrope et la tachycardie s'installent en trois à cinq minutes. Environ 75 % de la dose radiomarquée est excrétée, un quart dans les urines et la moitié dans les fèces, avec une disposition globalement comparable à celle du Δ9-THC.","metabolism":"Le 11-OH-THC est lui-même métabolisé par le CYP3A et le CYP2C9, ainsi que par glucuronidation via l'UGT2B7. Kumar et collaborateurs (2022) ont quantifié la part extrahépatique de ces réactions, importante après consommation orale par l'intestin et après inhalation par le poumon. La voie terminale est l'oxydation de l'alcool en acide 11-nor-9-carboxy-THC, métabolite inactif mais très persistant, qui se conjugue à l'acide glucuronique avant élimination.","detection":"Le 11-OH-THC est recherché en toxicologie par chromatographie liquide couplée à la spectrométrie de masse en tandem, dans le sang comme dans les urines. Sa présence conjointe avec le THC inchangé et l'acide 11-nor-9-carboxy-THC sert à estimer l'ancienneté d'une consommation : un rapport élevé de métabolites au THC oriente vers une prise ancienne ou orale, un THC prédominant vers une inhalation récente. Les immunoessais cannabis usuels ciblent en revanche l'acide carboxylique et non ce métabolite.","subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":45},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":15},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":60},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":80},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":85}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":"Le 11-OH-THC porte une part substantielle des effets indésirables attribués au cannabis ingéré : intensité inattendue, tachycardie, anxiété aiguë et épisodes de dépersonnalisation. Le décalage temporel propre à la voie orale, avec un effet qui met une à deux heures à s'installer, conduit fréquemment à une seconde prise avant l'apparition de la première, mécanisme classique des surdoses aux comestibles. Aucun seuil de sécurité n'est défini pour le métabolite pris isolément."},"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 on psychotropic substances, whose application Member States ensure. No marketing authorisation covers 11-OH-THC as an active substance; it is lawfully produced only as a reference standard for toxicology laboratories.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"11-OH-THC is first of all a metabolite formed in the body of anyone exposed to THC: its biological presence does not in itself constitute possession. As a hydroxylated derivative of tetrahydrocannabinol, it falls under the listing of THC and its derivatives in Annex IV of the arrêté of 22 February 1990 as soon as it is isolated, produced or transferred as a substance. It enters into the composition of no product that can be lawfully marketed in France.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Lemberger et coll. 1973 : pharmacologie comparée du Δ9-THC et du 11-OH-Δ9-THC chez l'humain","pmid":"4729039","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/4729039/"},{"label":"Lemberger et coll. 1972 : pharmacologie, disposition et métabolisme du 11-hydroxy-THC","pmid":"5041775","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/5041775/"},{"label":"Kumar et coll. 2022 : métabolisme extrahépatique du THC et du 11-OH-THC","pmid":"35370140","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/35370140/"}],"meta":{"slug":"11-oh-thc","url":"https://en.phytogrammes.com/wiki/11-oh-thc","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."}}