JWH-098

JWH-098
Legal status
Legal status	CA: Schedule II; UK: Class B;
Identifiers
	IUPAC name 4-methoxynaphthalen-1-yl-(1-pentyl-2-methylindol-3-yl)methanone;
CAS Number	316189-74-9;
PubChem CID	45272116;
ChemSpider	24628229;
CompTox Dashboard (EPA)	DTXSID80185501 ;
Chemical and physical data
Formula	C26H27NO2
Molar mass	385.497 g/mol 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;
	(verify)

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 10x selective for CB₁ over CB₂, in JWH-098 this is reversed, and it is around 4 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.^[1] JWH-098 is illegal in Russia,^[2] Sweden,^[3] and the UK,^[4] although it is unclear whether it has any history of human use.

References

^ Huffman JW, et al. Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB₁ and CB₂ receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB₂ receptor agonists. Bioorganic and Medicinal Chemistry. 2005; 13:89-112. PMID 15582455
^ "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. Retrieved 2010-09-09.
^ Svensk författningssamling
^ The Misuse of Drugs Act 1971 (Amendment) Order 2009

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[1] Huffman JW, et al. Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB₁ and CB₂ receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB₂ receptor agonists. Bioorganic and Medicinal Chemistry. 2005; 13:89-112. PMID 15582455

[2] "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. Retrieved 2010-09-09.

[3] Svensk författningssamling

[4] The Misuse of Drugs Act 1971 (Amendment) Order 2009

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See also

References