{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"RVLXSTGARMINHX-UHFFFAOYSA-N","prefName":"JWH-004","symbol":"JWH-004","iupacName":"(1-hexyl-2-methylindol-3-yl)-naphthalen-1-ylmethanone","aliases":["JWH 004","1-hexyl-2-méthyl-3-(1-naphtoyl)indole"],"cas":null,"pubchemCid":"44368388","chebiId":null,"smiles":"CCCCCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43)C","molecularFormula":"C26H27NO","molecularWeight":369.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/44368388"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic pathway: the molecule is produced by no living organism. It belongs solely to organic synthesis, which assembles a 2-methylindole core, a hexyl chain on the nitrogen and a 1-naphthoyl group at position 3. Manufacture is described here only by its chemical class.","originNote":"Entirely synthetic molecule. No plant species or living organism is recorded as a source of JWH-004, which is not a constituent of hemp. The sources consulted describe it only as a research compound, prepared in the laboratory to study the relationship between chemical structure and activity at cannabinoid receptors.","discovered":""},"pharmacology":{"summaryFr":"JWH-004, or 1-hexyl-2-methyl-3-(1-naphthoyl)indole, is a naphthoylindole of the JWH series, described in 1994 in Bioorganic & Medicinal Chemistry Letters. It displaces [3H]CP-55,940 with an inhibition constant of 48 nM, close to that of THC measured in the same publication (41 nM), and it shows cannabimimetic activity in mice, with a median effective dose (ED50) of 14 µmol/kg against 4.7 µmol/kg for THC. Among the straight-chain 2-methylated indoles, affinity peaks with a pentyl (9.5 nM for JWH-007) and falls sharply with a heptyl (more than 10 000 nM). No human pharmacokinetic, metabolic or toxicological data were found in the sources consulted. In France, it is classified as a narcotic under the generic definition of the indol-3-yl methanone family.","receptorSummaryFr":"A cannabinoid receptor ligand, active in vivo. In the 1994 publication, JWH-004 displaces the radioligand [3H]CP-55,940 with an inhibition constant (Ki) of 48 nM. ChEMBL files this measurement under the target « cannabinoid receptor », a family that includes CB1 and CB2 without distinguishing subtypes: the value cannot be attributed to either one alone. In the same publication, dronabinol (THC) shows a Ki of 41 nM and WIN 55,212-2 a Ki of 24 nM, so the affinity of JWH-004 is of the same order as that of THC. Among the straight-chain 2-methylated indoles, the constant varies with the length of the chain on the nitrogen: 164 nM with a propyl (JWH-015), 22 nM with a butyl, 9.5 nM with a pentyl (JWH-007), 48 nM with the hexyl of JWH-004, and more than 10 000 nM with a heptyl. In mice, cannabimimetic activity is measured with a median effective dose (ED50) of 14 µmol/kg, against 4.7 µmol/kg for THC and 2.62 µmol/kg for the pentyl (JWH-007), indicating lower in vivo potency than THC in this test. Aung et al. (2000) report that a chain of 3 to 6 carbons is sufficient for high affinity at CB1 and CB2, with no value specific to JWH-004 in the abstract consulted. Its intrinsic efficacy and any other targets are not documented in the sources consulted.","binding":[{"target":"CB1/CB2","efficacy":"full_agonist","relativeActivity":72,"reported":"Ki 48 nM, déplacement du [3H]CP-55,940 (Huffman et coll., 1994) ; cible ChEMBL « récepteur cannabinoïde » sans distinction de sous-type CB1 ou CB2","confidence":"medium"}],"references":[{"label":"Huffman JW, Dai D, Martin BR, Compton DR et coll., conception, synthèse et pharmacologie d'indoles cannabimimétiques, Bioorganic & Medicinal Chemistry Letters, 1994","pmid":null,"doi":"10.1016/S0960-894X(01)80155-4","url":"https://doi.org/10.1016/S0960-894X(01)80155-4"},{"label":"ChEMBL, fiche composé CHEMBL436268 (JWH-004) : Ki de 48 nM et DE50 de 14 µmol/kg, valeurs extraites de Huffman et coll., 1994","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL436268/"},{"label":"Wiley JL et coll., relations structure-activité des cannabinoïdes dérivés de l'indole et du pyrrole, longueur de chaîne optimale de quatre à six carbones, Journal of Pharmacology and Experimental Therapeutics, 1998","pmid":"9618400","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/9618400/"},{"label":"Aung MM et coll., influence de la longueur de la chaîne N-1 des indoles cannabimimétiques sur la liaison aux récepteurs CB1 et CB2, Drug and Alcohol Dependence, 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","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 des substances psychotropes sous contrôle international, 2026","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, Compound Summary CID 44368388, JWH-004","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/44368388"}]},"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":4},{"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":8},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":6}],"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 European Union control measure targets JWH-004 in the sources consulted: control falls to national legislation, including French law.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"A narcotic in France, through a generic family definition rather than a listing by name. JWH-004 is not named in the consolidated list of narcotics kept by the ANSM (update of 16 February 2026). It does, however, fall under annex IV, in the synthetic cannabinoid block, which classifies « any molecule belonging to the family of » indol-3-yl methanones meeting two conditions: an alkyl-type substituent on the indole nitrogen (the list also admits haloalkyl, halobenzyl, alkenyl, cycloalkylmethyl and other groups), and a naphthyl, benzyl, phenyl, cyclopropyl or adamantyl group, substituted or not, on the carbon of the methanone bridge. JWH-004 meets both conditions: its indole nitrogen carries a hexyl chain and its methanone bridge a naphthyl group. The definition sets no condition on position 2 of the indole, and the list cites as examples two 2-methylated indoles of the same series, JWH-007 and JWH-015.","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, Dai D, Martin BR, Compton DR et coll., conception, synthèse et pharmacologie d'indoles cannabimimétiques, Bioorganic & Medicinal Chemistry Letters, 1994","pmid":null,"doi":"10.1016/S0960-894X(01)80155-4","url":"https://doi.org/10.1016/S0960-894X(01)80155-4"},{"label":"ChEMBL, fiche composé CHEMBL436268 (JWH-004) : Ki de 48 nM et DE50 de 14 µmol/kg, valeurs extraites de Huffman et coll., 1994","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL436268/"},{"label":"Wiley JL et coll., relations structure-activité des cannabinoïdes dérivés de l'indole et du pyrrole, longueur de chaîne optimale de quatre à six carbones, Journal of Pharmacology and Experimental Therapeutics, 1998","pmid":"9618400","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/9618400/"},{"label":"Aung MM et coll., influence de la longueur de la chaîne N-1 des indoles cannabimimétiques sur la liaison aux récepteurs CB1 et CB2, Drug and Alcohol Dependence, 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","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 des substances psychotropes sous contrôle international, 2026","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, Compound Summary CID 44368388, JWH-004","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/44368388"}],"meta":{"slug":"jwh-004","url":"https://en.phytogrammes.com/wiki/jwh-004","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-12","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}