{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"QKXRHYJSCZFHEK-UHFFFAOYSA-N","prefName":"JWH-016","symbol":"JWH-016","iupacName":"(1-butyl-2-methylindol-3-yl)-naphthalen-1-ylmethanone","aliases":["JWH-016","1-butyl-2-methyl-3-(1-naphthoyl)indole","(1-butyl-2-methylindol-3-yl)-naphthalen-1-ylmethanone"],"cas":null,"pubchemCid":"44368310","chebiId":null,"smiles":"CCCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43)C","molecularFormula":"C24H23NO","molecularWeight":341.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/44368310"}},"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 comes only from organic synthesis, by acylation at position 3 of an N-butylated and 2-methylated indole. Manufacture is described here only by its chemical class.","originNote":"A wholly synthetic molecule: the chemical reference sources consulted record no natural occurrence, either in cannabis or in any other species. In the sources consulted, it appears only as a laboratory compound studied for the pharmacology of cannabinoid receptors.","discovered":""},"pharmacology":{"summaryFr":"JWH-016, or 1-butyl-2-methyl-3-(1-naphthoyl)indole, is a synthetic naphthoylindole described by John W. Huffman and his collaborators in 1994. It differs from JWH-073 only by a methyl group at position 2 of the indole. The measurement linked to this article gives a Ki of 22.0 nM for a cannabinoid receptor, the CB1 or CB2 subtype not being specified. No measure of efficacy specific to this compound, and no pharmacokinetic, metabolic or clinical data in humans, were found in the sources consulted: the record therefore remains limited to these elements.","receptorSummaryFr":"Reported affinity for a cannabinoid receptor whose subtype is not specified in the source: Ki of 22.0 nM, measured by displacement of [3H]CP-55,940 (Huffman et al., 1994). No separate affinity for CB1 or CB2 was found, and no measure of efficacy specific to this compound appears in the sources consulted: the agonist qualification follows that of the class of cannabimimetic indoles, without a direct measurement for this molecule. Aung et al. (2000) report, in a series of cannabimimetic indoles in which the N-1 chain varies, that an alkyl chain of 3 to 6 carbons suffices for high affinity at CB1 and CB2, with the optimum at 5 carbons; the butyl chain of JWH-016 falls within this range.","binding":[{"target":"Récepteur cannabinoïde (sous-type non précisé)","efficacy":"full_agonist","relativeActivity":78,"reported":"Ki 22,0 nM (déplacement du [3H]CP-55,940, Huffman et coll., 1994)","confidence":"medium"}],"references":[{"label":"Huffman JW et coll., Bioorganic and Medicinal Chemistry Letters, 1994 : conception, synthèse et pharmacologie des indoles cannabimimétiques (mesure Ki reprise de ChEMBL)","pmid":null,"doi":"10.1016/S0960-894X(01)80155-4","url":"https://doi.org/10.1016/S0960-894X(01)80155-4"},{"label":"ChEMBL, composé CHEMBL348654 (JWH-016), activité de liaison aux récepteurs cannabinoïdes, document CHEMBL1152041","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/api/data/activity.json?molecule_chembl_id=CHEMBL348654"},{"label":"Aung MM et coll., Drug and Alcohol Dependence, 2000 : influence de la longueur de la chaîne alkyle en N-1 des indoles cannabimimétiques sur la liaison aux récepteurs CB1 et CB2","pmid":"10940540","doi":"10.1016/s0376-8716(99)00152-0","url":"https://pubmed.ncbi.nlm.nih.gov/10940540/"},{"label":"Huffman JW et coll., Bioorganic and Medicinal Chemistry, 2005 : relations structure-activité des 1-alkyl-3-(1-naphtoyl)indoles, avec et sans méthyle en position 2, aux récepteurs CB1 et CB2","pmid":"15582455","doi":"10.1016/j.bmc.2004.09.050","url":"https://pubmed.ncbi.nlm.nih.gov/15582455/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026, annexe IV, clause 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":"Arrêté du 14 octobre 2019 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants, Légifrance","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000039223507"},{"label":"Organe international de contrôle des stupéfiants, Liste verte 2026 des substances psychotropes sous contrôle international","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, Compound Summary CID 44368310, JWH-016","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/44368310"}]},"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":8},{"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":"No harmonised control measure at European Union level has been identified for this compound in the sources consulted: control therefore rests on national legislation. It is not mentioned in the 2026 Green List of the International Narcotics Control Board, which lists the psychotropic substances under international control under the 1971 Convention.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Not named in annex IV of the decree of 22 February 1990 (ANSM consolidated list of 16 February 2026). It does, however, fall under the generic definition of the indol-3-yl methanone family, which covers an alkyl substituent on the indole nitrogen and a naphthyl group on the carbon of the methanone bridge: JWH-016 carries a butyl on the nitrogen and a 1-naphthyl on that carbon, and the definition does not restrict the other positions of the indole, so the methyl at position 2 is not excluded. JWH-007 and JWH-015, also 2-methylated, are named in the same annex. The classification therefore rests on this family clause, which is attached to the decree of 14 October 2019.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Huffman JW et coll., Bioorganic and Medicinal Chemistry Letters, 1994 : conception, synthèse et pharmacologie des indoles cannabimimétiques (mesure Ki reprise de ChEMBL)","pmid":null,"doi":"10.1016/S0960-894X(01)80155-4","url":"https://doi.org/10.1016/S0960-894X(01)80155-4"},{"label":"ChEMBL, composé CHEMBL348654 (JWH-016), activité de liaison aux récepteurs cannabinoïdes, document CHEMBL1152041","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/api/data/activity.json?molecule_chembl_id=CHEMBL348654"},{"label":"Aung MM et coll., Drug and Alcohol Dependence, 2000 : influence de la longueur de la chaîne alkyle en N-1 des indoles cannabimimétiques sur la liaison aux récepteurs CB1 et CB2","pmid":"10940540","doi":"10.1016/s0376-8716(99)00152-0","url":"https://pubmed.ncbi.nlm.nih.gov/10940540/"},{"label":"Huffman JW et coll., Bioorganic and Medicinal Chemistry, 2005 : relations structure-activité des 1-alkyl-3-(1-naphtoyl)indoles, avec et sans méthyle en position 2, aux récepteurs CB1 et CB2","pmid":"15582455","doi":"10.1016/j.bmc.2004.09.050","url":"https://pubmed.ncbi.nlm.nih.gov/15582455/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026, annexe IV, clause 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":"Arrêté du 14 octobre 2019 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants, Légifrance","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000039223507"},{"label":"Organe international de contrôle des stupéfiants, Liste verte 2026 des substances psychotropes sous contrôle international","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, Compound Summary CID 44368310, JWH-016","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/44368310"}],"meta":{"slug":"jwh-016","url":"https://en.phytogrammes.com/wiki/jwh-016","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."}}