JWH-004

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.

Source

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.

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.

European Union

No harmonised European Union control measure targets JWH-004 in the sources consulted: control falls to national legislation, including French law.

France

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.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

1. 1Huffman JW, Dai D, Martin BR, Compton DR et coll., conception, synthèse et pharmacologie d'indoles cannabimimétiques, Bioorganic & Medicinal Chemistry Letters, 1994 (new tab)DOI 10.1016/S0960-894X(01)80155-4
2. 2ChEMBL, fiche composé CHEMBL436268 (JWH-004) : Ki de 48 nM et DE50 de 14 µmol/kg, valeurs extraites de Huffman et coll., 1994 (new tab)
3. 3Wiley 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 (new tab)PMID 9618400
4. 4Aung 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 (new tab)PMID 10940540
5. 5ANSM, liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026, annexe IV, famille des indol-3-yl méthanones (new tab)
6. 6Organe international de contrôle des stupéfiants, liste verte des substances psychotropes sous contrôle international, 2026 (new tab)
7. 7PubChem, Compound Summary CID 44368388, JWH-004 (new tab)

SMILES

CCCCCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43)C

InChIKey

RVLXSTGARMINHX-UHFFFAOYSA-N

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.