{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"SKDUHKSZHNFWML-UHFFFAOYSA-N","prefName":"JWH-079","symbol":"JWH-079","iupacName":"(4-methoxynaphthalen-1-yl)-(1-propylindol-3-yl)methanone","aliases":["(4-methoxynaphthalen-1-yl)-(1-propylindol-3-yl)methanone","JWH-079","(4-methoxynaphthalen-1-yl)(1-propyl-1H-indol-3-yl)methanone"],"cas":null,"pubchemCid":"10831231","chebiId":null,"smiles":"CCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=C(C4=CC=CC=C43)OC","molecularFormula":"C23H21NO2","molecularWeight":343.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/10831231"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic pathway: JWH-079 is an organic synthetic compound of the naphthoylindole class, with no known equivalent in living organisms.","originNote":"Synthetic laboratory molecule of the JWH series, designed for the study of cannabinoid receptors. No consulted source reports it in a plant, in hemp or in a living organism.","discovered":""},"pharmacology":{"summaryFr":"JWH-079, or (4-methoxynaphthalen-1-yl)(1-propylindol-3-yl)methanone, belongs to the series of 1-alkyl-3-(1-naphthoyl)indoles developed by the team of John W. Huffman at Clemson University (Huffman et al., 2005). It differs from JWH-081 only by an N-propyl chain instead of an N-pentyl chain. In the modelling study by De Freitas et al. (2009), its Ki is 63.1 nM at CB1 and 31.99 nM at human CB2, similar affinities of a few tens of nanomolar. Its functional efficacy was not measured in the consulted sources, and no human, pharmacokinetic or toxicological data were found. The compound is not named in the French list of narcotics, but it falls under the generic clause of the indol-3-yl methanones.","receptorSummaryFr":"Synthetic ligand of CB1 and CB2, with nanomolar affinity. In the measurement published by De Freitas et al. (2009), the Ki is 63.1 nM at CB1 (rat brain) and 31.99 nM at human CB2: the two affinities are close, with CB2 bound about twice as strongly. No measure of intrinsic efficacy specific to this compound was found in the consulted sources, so the agonist classification used here rests on the chemical family and on the data for the series, not on a measurement for JWH-079 itself. A study of cannabimimetic indoles indicates that an N-alkyl chain of at least three carbons is required for high affinity at CB1 and CB2 (Aung et al., 2000), a condition met by the propyl group of JWH-079. No data on other targets were found in the consulted sources.","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":69,"reported":"Ki 63,1 nM (récepteur CB1 de cerveau de rat, déplacement du [3H]CP-55940) (De Freitas et coll., 2009)","confidence":"medium"},{"target":"CB2","efficacy":"full_agonist","relativeActivity":75,"reported":"Ki 31,99 nM (récepteur CB2 humain cloné, déplacement du [3H]CP-55940) (De Freitas et coll., 2009)","confidence":"medium"}],"references":[{"label":"De Freitas GB et coll., modèles CoMFA et CoMSIA de l'affinité et de la sélectivité des ligands indoliques pour les récepteurs CB1 et CB2, Eur J Med Chem, 2009","pmid":"19249138","doi":"10.1016/j.ejmech.2009.01.026","url":"https://pubmed.ncbi.nlm.nih.gov/19249138/"},{"label":"Huffman JW et coll., relations structure-activité des 1-alkyl-3-(1-naphtoyl)indoles sur les récepteurs CB1 et CB2, Bioorg Med Chem, 2005","pmid":"15582455","doi":"10.1016/j.bmc.2004.09.050","url":"https://pubmed.ncbi.nlm.nih.gov/15582455/"},{"label":"Aung MM et coll., influence de la longueur de la chaîne alkyle en N-1 des indoles cannabimimétiques sur la liaison CB1 et CB2, Drug Alcohol Depend, 2000","pmid":"10940540","doi":"10.1016/s0376-8716(99)00152-0","url":"https://pubmed.ncbi.nlm.nih.gov/10940540/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026, annexe IV, famille des indol-3-yl méthanones (entrée JWH-081)","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 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 10831231, JWH-079","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/10831231"},{"label":"ChEMBL, fiche composé CHEMBL561349 (JWH-079), mesures de déplacement de [3H]CP-55940","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL561349/"}]},"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":"There is no harmonised control measure at European Union level for this compound, as far as the consulted sources show: control is national. JWH-079 is not listed in the 2026 Green List of the International Narcotics Control Board, which lists the substances placed under 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 the consolidated list of narcotics published by the ANSM (updated 16 February 2026), JWH-079 nevertheless falls under the generic family of indol-3-yl methanones in annex IV of that list. That definition covers any molecule bearing on the indole nitrogen an alkyl-type substituent and, on the carbon of the methanone bridge, a naphthyl group, substituted or not. JWH-079 carries a propyl group on the nitrogen and a 4-methoxynaphthyl group on the bridge: it meets both conditions point by point, hence a classification through a generic clause and not through a listing by name. JWH-081, whose only difference from JWH-079 is a pentyl group in place of the propyl group, is cited by name among the examples of this family, in the same annex. JWH-079 is therefore classed as a narcotic under this 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":"De Freitas GB et coll., modèles CoMFA et CoMSIA de l'affinité et de la sélectivité des ligands indoliques pour les récepteurs CB1 et CB2, Eur J Med Chem, 2009","pmid":"19249138","doi":"10.1016/j.ejmech.2009.01.026","url":"https://pubmed.ncbi.nlm.nih.gov/19249138/"},{"label":"Huffman JW et coll., relations structure-activité des 1-alkyl-3-(1-naphtoyl)indoles sur les récepteurs CB1 et CB2, Bioorg Med Chem, 2005","pmid":"15582455","doi":"10.1016/j.bmc.2004.09.050","url":"https://pubmed.ncbi.nlm.nih.gov/15582455/"},{"label":"Aung MM et coll., influence de la longueur de la chaîne alkyle en N-1 des indoles cannabimimétiques sur la liaison CB1 et CB2, Drug Alcohol Depend, 2000","pmid":"10940540","doi":"10.1016/s0376-8716(99)00152-0","url":"https://pubmed.ncbi.nlm.nih.gov/10940540/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026, annexe IV, famille des indol-3-yl méthanones (entrée JWH-081)","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 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 10831231, JWH-079","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/10831231"},{"label":"ChEMBL, fiche composé CHEMBL561349 (JWH-079), mesures de déplacement de [3H]CP-55940","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL561349/"}],"meta":{"slug":"jwh-079","url":"https://en.phytogrammes.com/wiki/jwh-079","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."}}