{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"IRMPFYJSHJGOPE-UHFFFAOYSA-N","prefName":"Olivetol","symbol":"Olivetol","iupacName":"5-pentylbenzene-1,3-diol","aliases":["Olivétol","Olivetol","5-pentylrésorcinol","5-pentylbenzène-1,3-diol"],"cas":"500-66-3","pubchemCid":"10377","chebiId":"CHEBI:66960","smiles":"CCCCCC1=CC(=CC(=C1)O)O","molecularFormula":"C11H16O2","molecularWeight":180.24,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/10377","chebi":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:CHEBI:66960"}},"classification":{"family":"mineur","familyLabel":"Minor phytocannabinoid","origin":"natural","originLabel":"Naturel","structuralClassFr":null},"originSynthesis":{"heading":"Biosynthetic pathway","summaryFr":"Biosynthetic pathway: the hemp tetraketide synthase, a type III polyketide synthase, assembles a linear tetraketide intermediate. In the presence of olivetolic acid cyclase, a C2 to C7 aldol condensation with carboxylate retention gives olivetolic acid, the first intermediate of the cannabinoid pathway. In the absence of this cyclase, a non-enzymatic decarboxylative aldol condensation gives olivetol, a side product of the reaction. Olivetolic acid is then prenylated into cannabigerolic acid, from which THCA, CBDA and CBCA derive.","originNote":"A simple alkylresorcinol. In hemp it forms as a side product of the cannabinoid pathway, by decarboxylation of the precursor of olivetolic acid. It is not a cannabinoid: it is the phenolic half from which cannabinoids are built.","discovered":""},"pharmacology":{"summaryFr":"Olivetol (5-pentylresorcinol) is the alkylresorcinol that forms the aromatic core of the cannabinoids. In Cannabis sativa the pathway starts with a tetraketide synthase that assembles a linear intermediate; olivetolic acid cyclase, identified in 2012, closes it into olivetolic acid, the precursor of cannabigerolic acid. Without this cyclase the same reaction gives olivetol by decarboxylation, which explains why an enzyme cloned in 2009 was first named olivetol synthase. Olivetol is therefore not a cannabinoid but a side product of their biosynthesis and a classic intermediate of their chemical synthesis. At the human CB1 receptor, a 2022 study reports partial displacement of the radioligand (estimated Ki of 17 nM) with no measurable agonist activity.","receptorSummaryFr":"Olivetol is not an agonist of cannabinoid receptors. In a 2022 study on cells expressing the human CB1 receptor, it reduced binding of the radioligand CP55,940 with an estimated Ki of 17 nM, but displacement remained incomplete, which suggests a non-competitive mechanism. It does not inhibit cyclic AMP accumulation and does not recruit β-arrestin 2, and it does not alter the signalling induced by Δ9-THC. The authors do not rule out an indirect effect on the membrane rather than a direct interaction with the receptor.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":15,"reported":"Ki estimé à 17 nM en déplacement du CP55,940, déplacement incomplet ; aucune activité sur l'AMP cyclique ni sur la β-arrestine 2 (Zagzoog et coll., 2022)","confidence":"medium"}],"references":[{"label":"Gagne et coll., identification de la cyclase de l'acide olivétolique de Cannabis sativa, PNAS 2012","pmid":"22802619","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/22802619/"},{"label":"Taura et coll., caractérisation de l'olivétol synthase, polykétide synthase de la voie de biosynthèse des cannabinoïdes, FEBS Letters 2009","pmid":"19454282","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/19454282/"},{"label":"Kearsey et coll., structure de l'enzyme productrice d'olivétol de Cannabis sativa et plasticité de cyclisation des polykétide synthases de type III, FEBS Journal 2020","pmid":"31605668","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/31605668/"},{"label":"Zagzoog et coll., modulation de l'activité du récepteur cannabinoïde de type 1 par des sous-produits cannabinoïdes de Cannabis sativa et des phytomolécules non cannabiques, Frontiers in Pharmacology 2022","pmid":"36091813","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/36091813/"},{"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 10377 : olivétol (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/10377"}]},"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":6},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":4},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":4},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":4},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":2}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":null},"legal":{"scheduleStatus":"unscheduled","scheduleLabel":"Unscheduled","frScheduleStatus":"unscheduled","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 of its own at European Union level. The molecule appears in no schedule of the 1961 Convention on Narcotic Drugs or of the 1971 Convention on Psychotropic Substances. It holds no marketing authorisation and no novel food authorisation under Regulation (EU) 2015/2283: it circulates only as a chemical or reference standard intended for research.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Unscheduled substance. Olivetol is named in no annex of the order of 22 February 1990 and falls under no generic clause: it is neither a tetrahydrocannabinol nor a derivative of the benzo[c]chromene nucleus targeted by the ANSM decision of 22 May 2024. It is a laboratory chemical, with no status as a food or cosmetic ingredient.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Gagne et coll., identification de la cyclase de l'acide olivétolique de Cannabis sativa, PNAS 2012","pmid":"22802619","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/22802619/"},{"label":"Taura et coll., caractérisation de l'olivétol synthase, polykétide synthase de la voie de biosynthèse des cannabinoïdes, FEBS Letters 2009","pmid":"19454282","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/19454282/"},{"label":"Kearsey et coll., structure de l'enzyme productrice d'olivétol de Cannabis sativa et plasticité de cyclisation des polykétide synthases de type III, FEBS Journal 2020","pmid":"31605668","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/31605668/"},{"label":"Zagzoog et coll., modulation de l'activité du récepteur cannabinoïde de type 1 par des sous-produits cannabinoïdes de Cannabis sativa et des phytomolécules non cannabiques, Frontiers in Pharmacology 2022","pmid":"36091813","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/36091813/"},{"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 10377 : olivétol (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/10377"}],"meta":{"slug":"olivetol","url":"https://en.phytogrammes.com/wiki/olivetol","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-11","confidence":"high","dataCompletenessPct":80,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}