JWH-302

JWH-302

Identifiers
IUPAC name 2-(3-methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number	864445-45-4
PubChem (CID)	11493740
ChemSpider	9668546
ChEMBL	CHEMBL186674
Chemical and physical data
Formula	C22H25NO2
Molar mass	335.439 g/mol
3D model (Jmol)	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
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JWH-302 or (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]

References

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