{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"QHCQSGYWGBDSIY-HZPDHXFCSA-N","prefName":"Tetrahydrocannabutol","symbol":"Δ9-THCB","iupacName":"(6aR,10aR)-3-butyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol","aliases":["THCB","Δ9-THCB","Tétrahydrocannabutol","THC-C4","THC butylique","Butyl-Δ9-THC"],"cas":"60008-00-6","pubchemCid":"6453891","chebiId":null,"smiles":"CCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)O","molecularFormula":"C20H28O2","molecularWeight":300.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/6453891"}},"classification":{"family":"mineur","familyLabel":"Minor phytocannabinoid","origin":"natural","originLabel":"Naturel","structuralClassFr":null},"originSynthesis":{"heading":"Biosynthetic pathway","summaryFr":"Biosynthetic pathway: Δ9-THCB belongs to the butyl series of cannabinoids, a minor one in the plant, in which the olivetolic acid type precursor carries a four-carbon chain instead of five. Prenylation followed by enzymatic cyclisation leads to the corresponding acid, whose decarboxylation releases Δ9-THCB. This pathway is inferred by analogy with that of THC and has not been demonstrated enzyme by enzyme for the butyl series.","originNote":"Cannabis sativa L.: isolated from the inflorescences of the Italian medical variety FM2, where it occurs only in trace amounts.","discovered":""},"pharmacology":{"summaryFr":"Δ9-tetrahydrocannabutol (Δ9-THCB) is the butyl side-chain homologue of Δ9-THC, isolated in 2020 by Linciano, Citti and Cannazza's team from the medical cannabis variety FM2, together with cannabidibutol. Its structure was established by nuclear magnetic resonance, ultraviolet and infrared spectroscopy, circular dichroism and high-resolution mass spectrometry, then confirmed by stereoselective synthesis. Its affinity for the human CB1 (Ki of 15 nM) and CB2 (Ki of 51 nM) receptors is comparable to that of THC, and the tetrad test in mice shows partial agonist activity at CB1. No human data exist. In France the molecule is caught by the generic clause of Annex IV of the order of 22 February 1990 and by that of the ANSM decision of 22 May 2024.","receptorSummaryFr":"Δ9-THCB binds human cannabinoid receptors with an affinity comparable to that of (-)-trans-Δ9-THC: Ki of 15 nM at CB1 and 51 nM at CB2 according to the isolation study. In mice, the tetrad test indicates partial agonist activity at the CB1 receptor. The authors also ran a formalin test to explore possible analgesic and anti-inflammatory properties. No human data exist.","binding":[{"target":"CB1","efficacy":"partial_agonist","relativeActivity":88,"reported":"Ki 15 nM (CB1 humain) ; agoniste partiel au test de la tétrade chez la souris","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":70,"reported":"Ki 51 nM (CB2 humain) ; efficacité fonctionnelle non caractérisée","confidence":"medium"}],"references":[{"label":"Linciano, Citti et coll., isolement du Δ9-tétrahydrocannabutol, homologue butyle du Δ9-THC à haute affinité pour le récepteur CB1 humain, Journal of Natural Products 2020","pmid":"31891265","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/31891265/"},{"label":"ANSM, Décision du 22 mai 2024 portant modification de la liste des substances classées comme stupéfiants (clause générique benzo[c]chromène)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/actualites/decision-du-22-05-2024-portant-modification-de-la-liste-des-substances-classees-comme-stupefiants"},{"label":"Légifrance, annexe IV de l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/loda/article_lc/LEGIARTI000020689963/"},{"label":"PubChem CID 6453891 : tétrahydrocannabutol (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/6453891"}]},"pharmacokinetics":null,"metabolism":null,"detection":null,"subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":15},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":8},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":12},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":15},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":18}],"doseRanges":null,"humanDataCharacterised":false},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":true,"bannerTextFr":"Aucune dose humaine caractérisée : données animales / in vitro uniquement. Profil d'effet, marge de sécurité et toxicité aiguë non documentés en clinique humaine.","toxicologyFr":null},"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":"No control measure at European Union level names Δ9-THCB. Effective control remains a national competence and the status varies from one Member State to another, several countries having adopted, like France, generic definitions covering THC homologues.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Prohibited in France by a generic clause, without being named. Annex IV of the order of 22 February 1990 classifies as narcotics the tetrahydrocannabinols, their esters, ethers and salts, as well as the salts of those derivatives. The ANSM decision of 22 May 2024 added any substance derived from the benzo[c]chromene nucleus substituted notably at position 1 by a hydroxyl group, at position 3 by an alkyl chain, at position 6 by one or two alkyl groups and at position 9 by an alkyl group: Δ9-THCB matches that description. Its status is therefore that of a narcotic caught by a generic clause.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Linciano, Citti et coll., isolement du Δ9-tétrahydrocannabutol, homologue butyle du Δ9-THC à haute affinité pour le récepteur CB1 humain, Journal of Natural Products 2020","pmid":"31891265","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/31891265/"},{"label":"ANSM, Décision du 22 mai 2024 portant modification de la liste des substances classées comme stupéfiants (clause générique benzo[c]chromène)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/actualites/decision-du-22-05-2024-portant-modification-de-la-liste-des-substances-classees-comme-stupefiants"},{"label":"Légifrance, annexe IV de l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/loda/article_lc/LEGIARTI000020689963/"},{"label":"PubChem CID 6453891 : tétrahydrocannabutol (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/6453891"}],"meta":{"slug":"thcb","url":"https://en.phytogrammes.com/wiki/thcb","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-11","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}