JWH-302

JWH-302
Legal status
Legal status	US: Schedule I ;
Identifiers
	IUPAC name 2-(3-Methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone;
CAS Number	864445-45-4 ;
PubChem CID	11493740;
ChemSpider	9668546 ;
ChEMBL	ChEMBL186674 ;
CompTox Dashboard (EPA)	DTXSID60467554 ;
Chemical and physical data
Formula	C22H25NO2
Molar mass	335.447 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c2ccc(OC)cc2CC(=O)c(cn1CCCCC)c3ccccc13;
	InChI InChI=1S/C22H25NO2/c1-3-4-7-13-23-16-20(19-11-5-6-12-21(19)23)22(24)15-17-9-8-10-18(14-17)25-2/h5-6,8-12,14,16H,3-4,7,13,15H2,1-2H3 ; Key:XZVYWLVYUAQEIM-UHFFFAOYSA-N ;
(what is this?) (verify)

JWH-302 (1-pentyl-3-(3-methoxyphenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family, which acts as a cannabinoid agonist with moderate affinity at both the CB₁ and CB₂ receptors. It is a positional isomer of the more common drug JWH-250, though it is slightly less potent with a K_i of 17 nM at CB₁, compared to 11 nM for JWH-250.[1][2] Because of their identical molecular weight and similar fragmentation patterns, JWH-302 and JWH-250 can be very difficult to distinguish by GC-MS testing.[3]

In the United States, CB₁ receptor agonists of the 3-phenylacetylindole class such as JWH-302 are Schedule I Controlled Substances.[4]

References

Huffman, JW.; et al. (2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters. 15 (18): 4110–3. doi:10.1016/j.bmcl.2005.06.008. PMID 16005223.
Manera, C; Tuccinardi, T; Martinelli, A (2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.
'Herbal High' synthetic Cannabinoid composition, released by ESR July 2011
21 U.S.C. § 812: Schedules of controlled substances

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Huffman, JW.; et al. (2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters. 15 (18): 4110–3. doi:10.1016/j.bmcl.2005.06.008. PMID 16005223.

[2] Manera, C; Tuccinardi, T; Martinelli, A (2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.

[3] 'Herbal High' synthetic Cannabinoid composition, released by ESR July 2011

[4] 21 U.S.C. § 812: Schedules of controlled substances