{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"YSHKYTNQWIZJFW-ZWKOTPCHSA-N","prefName":"JWH-139","symbol":"JWH-139","iupacName":"(6aR,10aR)-6,6,9-trimethyl-3-(2-methylbutan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene","aliases":["JWH-139","910865DJI7","3-(1',1'-Dimethylpropyl)-1-deoxy-delta8-THC"],"cas":null,"pubchemCid":"58683014","chebiId":null,"smiles":"CCC(C)(C)C1=CC2=C(C=C1)[C@@H]3CC(=CC[C@H]3C(O2)(C)C)C","molecularFormula":"C21H30O","molecularWeight":298.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/58683014"}},"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-139 is produced by no living organism. It belongs to synthetic chemistry alone, within the chemistry of THC analogues.","originNote":"A synthetic molecule with no known plant origin. It was designed as a research tool for cannabinoid receptors, not as a medicine.","discovered":""},"pharmacology":{"summaryFr":"JWH-139 is a 1-deoxy analogue of Δ8-THC, part of the series by Huffman et al. (1999) devoted to the search for selective CB2 receptor ligands. In the reported measurements, its affinity is high for CB2 (Ki of 14.0 nM according to the ChEMBL database) and low for CB1 (Ki of 2 290 nM at the rat receptor), while the abstract of the article reports, for the analogues of the series with n from 1 to 4, a Ki above 295 nM at CB1. No functional efficacy, pharmacokinetic or human trial data were found in the sources consulted. In France it is not named in the list of narcotics, but it falls under the generic clause for the benzo[c]chromene nucleus (decision of 22 May 2024).","receptorSummaryFr":"A synthetic ligand with a markedly stronger affinity for the CB2 receptor than for CB1. The ChEMBL database reports a Ki of 14.0 nM at human CB2 and 2 290 nM at rat CB1 (Mangiatordi et al., 2020). In the series of Huffman et al. (1999), the abstract reports a Ki below 20 nM at CB2 for analogues with n from 1 to 5, and a Ki above 295 nM at CB1 for analogues with n from 1 to 4. The abstract gives no individual value for JWH-139. No functional efficacy data, agonist or antagonist, were found in the sources consulted. No human data were found in the sources consulted.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":27,"reported":"Ki 2 290 nM sur CB1 de rat (Mangiatordi et coll., 2020, via ChEMBL) ; série de Huffman et coll., 1999 : Ki supérieur à 295 nM pour les termes n = 1 à 4","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":82,"reported":"Ki 14,0 nM sur CB2 humain (Mangiatordi et coll., 2020, via ChEMBL) ; série de Huffman et coll., 1999 : Ki inférieur à 20 nM pour les termes n = 1 à 5","confidence":"medium"}],"references":[{"label":"Huffman et coll., 3-(1',1'-diméthylbutyl)-1-désoxy-Δ8-THC et composés apparentés : synthèse de ligands sélectifs du récepteur CB2, Bioorganic and Medicinal Chemistry, 1999","pmid":"10658595","doi":"10.1016/s0968-0896(99)00219-9","url":"https://pubmed.ncbi.nlm.nih.gov/10658595/"},{"label":"Mangiatordi et coll., le récepteur cannabinoïde de sous-type 2 (CB2R) dans une approche multicible : perspective, Journal of Medicinal Chemistry, 2020 (document source des valeurs Ki rapportées par ChEMBL)","pmid":"33094613","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33094613/"},{"label":"ChEMBL, fiche composé CHEMBL5281620 (affinités Ki CB1 et CB2 du JWH-139)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL5281620/"},{"label":"PubChem CID 58683014 : JWH-139 (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/58683014"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026), annexe IV, clause du noyau benzo[c]chromène issue de la décision du 22 mai 2024","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (substances des tableaux de la Convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}]},"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":5},{"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":8},{"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":5}],"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 was identified for JWH-139 in the sources consulted: control therefore falls to the Member States, whose individual situations were not checked.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"JWH-139 is not named in the ANSM consolidated list of narcotics (update of 16 February 2026). It does, however, fall under the generic clause of the 22 May 2024 decision (Annex IV of that list), which covers any derivative of the benzo[c]chromene nucleus, unhydrogenated or partially or fully hydrogenated on ring A, « substituted or not at one of the following positions of the nucleus »: position 1 (hydroxyl or alkoxy), positions 2 or 4 (carboxyl), position 3 (alkyl chain and related groups), position 6 (one or two alkyl groups), or position 9 (ketone, alkyl, hydroxyalkyl or alkoxy). JWH-139 has this nucleus, partially hydrogenated on ring A, and carries an alkyl group at position 3 (2-methylbutan-2-yl), two alkyl groups at position 6 and an alkyl group at position 9: it meets the condition, since the clause requires only one of these positions. None of the clause's exclusions (cannabinol, THCV, THCA) applies. It is not listed in the INCB Green List 2026, where all entries for this family (THC and its isomers, HHC, parahexyl, DMHP) carry a hydroxyl group at position 1.","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 et coll., 3-(1',1'-diméthylbutyl)-1-désoxy-Δ8-THC et composés apparentés : synthèse de ligands sélectifs du récepteur CB2, Bioorganic and Medicinal Chemistry, 1999","pmid":"10658595","doi":"10.1016/s0968-0896(99)00219-9","url":"https://pubmed.ncbi.nlm.nih.gov/10658595/"},{"label":"Mangiatordi et coll., le récepteur cannabinoïde de sous-type 2 (CB2R) dans une approche multicible : perspective, Journal of Medicinal Chemistry, 2020 (document source des valeurs Ki rapportées par ChEMBL)","pmid":"33094613","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33094613/"},{"label":"ChEMBL, fiche composé CHEMBL5281620 (affinités Ki CB1 et CB2 du JWH-139)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL5281620/"},{"label":"PubChem CID 58683014 : JWH-139 (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/58683014"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026), annexe IV, clause du noyau benzo[c]chromène issue de la décision du 22 mai 2024","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (substances des tableaux de la Convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}],"meta":{"slug":"jwh-139","url":"https://en.phytogrammes.com/wiki/jwh-139","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."}}