JWH-098

JWH-098

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Class B US: Schedule I
Identifiers
IUPAC name 4-Methoxynaphthalen-1-yl-(1-pentyl-2-methylindol-3-yl)methanone
CAS Number	316189-74-9
PubChem CID	45272116
ChemSpider	24628229
UNII	T27V33219F
CompTox Dashboard (EPA)	DTXSID80185501
Chemical and physical data
Formula	C26H27NO2
Molar mass	385.507 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCCCCn(c1C)c2ccccc2c1C(=O)c(ccc3OC)c4ccccc34
InChI InChI=1S/C26H27NO2/c1-4-5-10-17-27-18(2)25(22-13-8-9-14-23(22)27)26(28)21-15-16-24(29-3)20-12-7-6-11-19(20)21/h6-9,11-16H,4-5,10,17H2,1-3H3 Key:CNTCHEBQQFICNR-UHFFFAOYSA-N
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JWH-098 is a synthetic cannabinoid receptor agonist from the naphthoylindole family. It is the indole 2-methyl derivative of a closely related compound JWH-081, but has markedly different affinity for the CB₁ and CB₂ receptors. While JWH-081 is around tenfold selective for CB₁ over CB₂, in JWH-098 this is reversed, and it is around four times weaker than JWH-081 at CB₁ while being six times more potent at CB₂, giving it a slight selectivity for CB₂ overall. This makes JWH-098 a good example of how methylation of the indole 2-position in the naphthoylindole series tends to increase CB₂ affinity, but often at the expense of CB₁ binding.^[2]

Legal status

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-098 are Schedule I Controlled Substances.^[3]

JWH-098 is illegal in Russia,^[4] Sweden,^[5] and the UK,^[6] although it is unclear whether it has any history of human use.

See also

• JWH-007
• JWH-081

References

1. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
2. Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
3. 21 U.S.C. § 812: Schedules of controlled substances
4. "Постановление от 31 декабря 2009 г. № 1186 О внесении изменений в некоторые постановления Правительства Российской Федерации по вопросам, связанным с оборотом наркотических средств". Government.ru. Archived from the original on 2010-09-29. Retrieved 2010-09-09.
5. Svensk författningssamling
6. The Misuse of Drugs Act 1971 (Amendment) Order 2009 Archived 2009-11-03 at the Wayback Machine