{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"IHKDUDCDUKFOKK-UHFFFAOYSA-N","prefName":"JWH-020","symbol":"JWH-020","iupacName":"(1-heptylindol-3-yl)-naphthalen-1-ylmethanone","aliases":["JWH 020","(1-heptyl-1H-indol-3-yl)(naphthalen-1-yl)methanone","(1-heptylindol-3-yl)-naphthalen-1-ylmethanone","1-heptyl-3-(1-naphthoyl)indole"],"cas":null,"pubchemCid":"10406802","chebiId":null,"smiles":"CCCCCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43","molecularFormula":"C26H27NO","molecularWeight":369.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/10406802"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No known biosynthetic pathway: the molecule results from organic synthesis, by acylation of an indole bearing a heptyl chain on the nitrogen with a naphthalene-1-carbonyl unit. Manufacture is described here only by its chemical class.","originNote":"Entirely synthetic molecule, with no natural occurrence recorded in cannabis. It was described as a new compound in 1995 in a pharmacological study, then analysed in forensic toxicology as a synthetic cannabinoid.","discovered":""},"pharmacology":{"summaryFr":"JWH-020 belongs to the naphthoylindoles, a family of synthetic agonists of cannabinoid receptors: an indole ring carries a naphthoyl group at position 3 and a heptyl chain on the nitrogen. Measured on the mouse vas deferens, it inhibits electrically evoked contractions with an IC50 of 639 nM, and its effect is antagonised by SR141716A, a selective CB1 antagonist. A 2000 study reports that extending the chain to heptyl sharply reduces binding at both receptors, though the abstract consulted gives no value for this specific compound. No binding constant (Ki) and no human usage data are published in the sources consulted, so its risk profile remains poorly characterised.","receptorSummaryFr":"Agonist of cannabinoid receptors, whose effect on the mouse vas deferens is antagonised by SR141716A, a selective CB1 antagonist, with a Kd of 8.06 nM for that antagonist (Pertwee et al., 1995). The measured IC50 is 639 nM, markedly less potent than the two other compounds in the same study (2.56 and 3.38 nM). The sources consulted publish neither a binding constant (Ki) nor an affinity value for this compound, at CB1 or CB2. A 2000 study reports that extending the N-1 chain up to heptyl sharply reduces binding at both receptors, whereas 3 to 6 carbons suffice for high affinity (Aung et al., 2000). The optimal chain length in this series lies between 4 and 6 carbons (Wiley et al., 1998).","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":45,"reported":"CI50 639 nM (inhibition des contractions électriques du canal déférent de souris, Pertwee et coll., 1995) ; aucune constante Ki publiée dans les résumés consultés","confidence":"medium"}],"references":[{"label":"Pertwee RG et coll., European Journal of Pharmacology, 1995 : caractérisation de trois agonistes cannabinoïdes dont le 1-heptyl-3-(1-naphtoyl)indole, sur le canal déférent de souris","pmid":"8666005","doi":"10.1016/0014-2999(95)00318-f","url":"https://pubmed.ncbi.nlm.nih.gov/8666005/"},{"label":"Aung MM et coll., Drug and Alcohol Dependence, 2000 : influence de la longueur de la chaîne N-1 des indoles cannabimimétiques sur la liaison CB1 et CB2","pmid":"10940540","doi":"10.1016/s0376-8716(99)00152-0","url":"https://pubmed.ncbi.nlm.nih.gov/10940540/"},{"label":"Wiley JL et coll., Journal of Pharmacology and Experimental Therapeutics, 1998 : relations structure-activité des cannabinoïdes dérivés de l'indole et du pyrrole","pmid":"9618400","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/9618400/"},{"label":"Dresen S et coll., Journal of Mass Spectrometry, 2011 : dosage LC-MS/MS des aminoalkylindoles de synthèse dans le sérum, appliqué à des échantillons médico-légaux","pmid":"21259394","doi":"10.1002/jms.1877","url":"https://pubmed.ncbi.nlm.nih.gov/21259394/"},{"label":"Hutter M et coll., Journal of Chromatography B, 2012 : dosage de 22 cannabinoïdes de synthèse dans les cheveux humains par LC-MS/MS","pmid":"22835826","doi":"10.1016/j.jchromb.2012.07.002","url":"https://pubmed.ncbi.nlm.nih.gov/22835826/"},{"label":"Uchiyama N et coll., Yakugaku Zasshi, 2015 : évaluation d'un test de dépistage sur site des cannabinoïdes de synthèse dans les produits à base de plantes","pmid":"25759062","doi":"10.1248/yakushi.14-00247","url":"https://pubmed.ncbi.nlm.nih.gov/25759062/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026, annexe IV, définition de famille des indol-3-yl méthanones","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"Organe international de contrôle des stupéfiants, Liste verte 2026 des substances psychotropes (tableaux de la convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, Compound Summary CID 10406802, JWH-020","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/10406802"}]},"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":10},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":5},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":10},{"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":8}],"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":"unscheduled","scheduleLabel":"Unscheduled","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":"The sources consulted document no European Union control measure for this compound. At international level, it is absent from the 2026 Green List of the International Narcotics Control Board, which notably lists JWH-018 and AM-2201. Outside the Union, Uchiyama et al. (2015) classify it among the designated substances in Japan.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Classed as a narcotic in France through a generic family definition, without being named on the list. The consolidated ANSM list of 16 February 2026 does not name JWH-020 explicitly. Its structure does, however, meet the three conditions of the indol-3-yl methanone family (annex IV of the decree of 22 February 1990): a methanone bridge at position 3 of the indole ring, an alkyl substituent on the indole nitrogen (a heptyl chain), and a naphthyl group on the methanone carbon. The classification therefore rests on this family clause, not on a listing by name.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Pertwee RG et coll., European Journal of Pharmacology, 1995 : caractérisation de trois agonistes cannabinoïdes dont le 1-heptyl-3-(1-naphtoyl)indole, sur le canal déférent de souris","pmid":"8666005","doi":"10.1016/0014-2999(95)00318-f","url":"https://pubmed.ncbi.nlm.nih.gov/8666005/"},{"label":"Aung MM et coll., Drug and Alcohol Dependence, 2000 : influence de la longueur de la chaîne N-1 des indoles cannabimimétiques sur la liaison CB1 et CB2","pmid":"10940540","doi":"10.1016/s0376-8716(99)00152-0","url":"https://pubmed.ncbi.nlm.nih.gov/10940540/"},{"label":"Wiley JL et coll., Journal of Pharmacology and Experimental Therapeutics, 1998 : relations structure-activité des cannabinoïdes dérivés de l'indole et du pyrrole","pmid":"9618400","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/9618400/"},{"label":"Dresen S et coll., Journal of Mass Spectrometry, 2011 : dosage LC-MS/MS des aminoalkylindoles de synthèse dans le sérum, appliqué à des échantillons médico-légaux","pmid":"21259394","doi":"10.1002/jms.1877","url":"https://pubmed.ncbi.nlm.nih.gov/21259394/"},{"label":"Hutter M et coll., Journal of Chromatography B, 2012 : dosage de 22 cannabinoïdes de synthèse dans les cheveux humains par LC-MS/MS","pmid":"22835826","doi":"10.1016/j.jchromb.2012.07.002","url":"https://pubmed.ncbi.nlm.nih.gov/22835826/"},{"label":"Uchiyama N et coll., Yakugaku Zasshi, 2015 : évaluation d'un test de dépistage sur site des cannabinoïdes de synthèse dans les produits à base de plantes","pmid":"25759062","doi":"10.1248/yakushi.14-00247","url":"https://pubmed.ncbi.nlm.nih.gov/25759062/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026, annexe IV, définition de famille des indol-3-yl méthanones","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"Organe international de contrôle des stupéfiants, Liste verte 2026 des substances psychotropes (tableaux de la convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, Compound Summary CID 10406802, JWH-020","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/10406802"}],"meta":{"slug":"jwh-020","url":"https://en.phytogrammes.com/wiki/jwh-020","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-13","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}