{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"JLXYYSHMURZHKI-UHFFFAOYSA-N","prefName":"JWH-145","symbol":"JWH-145","iupacName":"naphthalen-1-yl-(1-pentyl-5-phenylpyrrol-3-yl)methanone","aliases":["JWH 145","naphthalen-1-yl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)methanone","1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone"],"cas":"914458-19-8","pubchemCid":"44418304","chebiId":null,"smiles":"O=C(C1=CN(CCCCC)C(C2=CC=CC=C2)=C1)C3=C(C=CC=C4)C4=CC=C3","molecularFormula":"C26H25NO","molecularWeight":367.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/44418304"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic route: JWH-145 is produced by no living organism. It belongs solely to synthetic chemistry.","originNote":"Entirely synthetic molecule: no plant, including hemp, is reported as a natural source of this compound. It is produced in the laboratory, as part of pharmacological work on cannabinoid receptors. The review by Wiley et al. (2014) indicates that indole- and pyrrole-derived synthetic cannabinoids are among the most common psychoactive compounds in products sold as spice. No consulted source documents the presence of JWH-145 in these products.","discovered":""},"pharmacology":{"summaryFr":"JWH-145 is a synthetic naphthoylpyrrole, chemically named naphthalen-1-yl-(1-pentyl-5-phenylpyrrol-3-yl)methanone. Huffman et al. (2006) report affinities of 14.0 nM at CB1 and 6.4 nM at CB2, values recorded in ChEMBL. It is named as a narcotic in France. No human, pharmacokinetic or toxicological data is published in the sources consulted, and its own functional efficacy remains undocumented.","receptorSummaryFr":"Nanomolar affinities at both receptors: Ki of 14.0 nM at CB1 (rat brain) and 6.4 nM at cloned human CB2, according to Huffman et al. (2006), data recorded in ChEMBL. That publication reports CB1 affinities in the 6 to 30 nM range for several compounds in its two series. Its abstract does not describe the functional efficacy of each compound: the functional efficacy of JWH-145 itself is therefore not documented in the sources consulted. The review by Wiley et al. (2014) observes, on derivatives of the prototype WIN 55,212-2, that replacing the indole core with a pyrrole or phenylpyrrole core retains CB1 affinity and in vivo cannabimimetic activity; JWH-145 is not named in the abstract consulted.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":82,"reported":"Ki 14,0 nM (Huffman et coll., 2006)","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":87,"reported":"Ki 6,4 nM (Huffman et coll., 2006)","confidence":"medium"}],"references":[{"label":"Huffman et coll., 1-alkyl-2-aryl-4-(1-naphtoyl)pyrroles, affinités CB1 et CB2, Bioorg Med Chem Lett 2006","pmid":"16889960","doi":"10.1016/j.bmcl.2006.07.051","url":"https://pubmed.ncbi.nlm.nih.gov/16889960/"},{"label":"Wiley et coll., relation structure et activité in vivo des cannabinoïdes de synthèse, Life Sci 2014","pmid":"24071522","doi":"10.1016/j.lfs.2013.09.011","url":"https://pubmed.ncbi.nlm.nih.gov/24071522/"},{"label":"Evans-Newman et coll., classification des spectres de masse des cannabinoïdes de synthèse, Molecules 2024","pmid":"39407576","doi":"10.3390/molecules29194646","url":"https://pubmed.ncbi.nlm.nih.gov/39407576/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe IV, famille des naphtoylpyrroles)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"PubChem, CID 44418304 (JWH-145)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/44418304"},{"label":"ChEMBL, CHEMBL385940 (JWH-145)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL385940/"}]},"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":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":10}],"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-named","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 European Union control measure for this compound was found in the sources consulted: its status rests, for now, on national legislation.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"JWH-145 is named in France. It appears in the definition of the naphthoylpyrrole family, in Annex IV of the consolidated list of substances classed as narcotics (updated 16 February 2026), where it is designated « 1-naphthalenyl (1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone ». It is therefore classed as a narcotic in France.","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., 1-alkyl-2-aryl-4-(1-naphtoyl)pyrroles, affinités CB1 et CB2, Bioorg Med Chem Lett 2006","pmid":"16889960","doi":"10.1016/j.bmcl.2006.07.051","url":"https://pubmed.ncbi.nlm.nih.gov/16889960/"},{"label":"Wiley et coll., relation structure et activité in vivo des cannabinoïdes de synthèse, Life Sci 2014","pmid":"24071522","doi":"10.1016/j.lfs.2013.09.011","url":"https://pubmed.ncbi.nlm.nih.gov/24071522/"},{"label":"Evans-Newman et coll., classification des spectres de masse des cannabinoïdes de synthèse, Molecules 2024","pmid":"39407576","doi":"10.3390/molecules29194646","url":"https://pubmed.ncbi.nlm.nih.gov/39407576/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe IV, famille des naphtoylpyrroles)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"PubChem, CID 44418304 (JWH-145)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/44418304"},{"label":"ChEMBL, CHEMBL385940 (JWH-145)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL385940/"}],"meta":{"slug":"jwh-145","url":"https://en.phytogrammes.com/wiki/jwh-145","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."}}