JWH-016

JWH-016, or 1-butyl-2-methyl-3-(1-naphthoyl)indole, is a synthetic naphthoylindole described by John W. Huffman and his collaborators in 1994. It differs from JWH-073 only by a methyl group at position 2 of the indole. The measurement linked to this article gives a Ki of 22.0 nM for a cannabinoid receptor, the CB1 or CB2 subtype not being specified. No measure of efficacy specific to this compound, and no pharmacokinetic, metabolic or clinical data in humans, were found in the sources consulted: the record therefore remains limited to these elements.

Source

A wholly synthetic molecule: the chemical reference sources consulted record no natural occurrence, either in cannabis or in any other species. In the sources consulted, it appears only as a laboratory compound studied for the pharmacology of cannabinoid receptors.

No known biosynthetic pathway: the molecule comes only from organic synthesis, by acylation at position 3 of an N-butylated and 2-methylated indole. Manufacture is described here only by its chemical class.

European Union

No harmonised control measure at European Union level has been identified for this compound in the sources consulted: control therefore rests on national legislation. It is not mentioned in the 2026 Green List of the International Narcotics Control Board, which lists the psychotropic substances under international control under the 1971 Convention.

France

Not named in annex IV of the decree of 22 February 1990 (ANSM consolidated list of 16 February 2026). It does, however, fall under the generic definition of the indol-3-yl methanone family, which covers an alkyl substituent on the indole nitrogen and a naphthyl group on the carbon of the methanone bridge: JWH-016 carries a butyl on the nitrogen and a 1-naphthyl on that carbon, and the definition does not restrict the other positions of the indole, so the methyl at position 2 is not excluded. JWH-007 and JWH-015, also 2-methylated, are named in the same annex. The classification therefore rests on this family clause, which is attached to the decree of 14 October 2019.

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

1. 1Huffman JW et coll., Bioorganic and Medicinal Chemistry Letters, 1994 : conception, synthèse et pharmacologie des indoles cannabimimétiques (mesure Ki reprise de ChEMBL) (new tab)DOI 10.1016/S0960-894X(01)80155-4
2. 2ChEMBL, composé CHEMBL348654 (JWH-016), activité de liaison aux récepteurs cannabinoïdes, document CHEMBL1152041 (new tab)
3. 3Aung MM et coll., Drug and Alcohol Dependence, 2000 : influence de la longueur de la chaîne alkyle en N-1 des indoles cannabimimétiques sur la liaison aux récepteurs CB1 et CB2 (new tab)PMID 10940540
4. 4Huffman JW et coll., Bioorganic and Medicinal Chemistry, 2005 : relations structure-activité des 1-alkyl-3-(1-naphtoyl)indoles, avec et sans méthyle en position 2, aux récepteurs CB1 et CB2 (new tab)PMID 15582455
5. 5ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026, annexe IV, clause de famille des indol-3-yl méthanones (new tab)
6. 6Arrêté du 14 octobre 2019 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants, Légifrance (new tab)
7. 7Organe international de contrôle des stupéfiants, Liste verte 2026 des substances psychotropes sous contrôle international (new tab)
8. 8PubChem, Compound Summary CID 44368310, JWH-016 (new tab)

SMILES

CCCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43)C

InChIKey

QKXRHYJSCZFHEK-UHFFFAOYSA-N

Machine-readable entry (JSON)

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