JWH-203

JWH-203

Legal status
Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I I-N (Poland)[1]
Identifiers
IUPAC name 2-(2-Chlorophenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number	864445-54-5 Y (JWH-203) 864445-55-6 (JWH-204)
PubChem CID	44397500
ChemSpider	23256082
UNII	52CP80V8FY
CompTox Dashboard (EPA)	DTXSID00235557
ECHA InfoCard	100.233.381
Chemical and physical data
Formula	C21H22ClNO
Molar mass	339.86 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc2ccccc2CC(=O)c1cn(CCCCC)c3ccccc13
InChI InChI=1S/C21H22ClNO/c1-2-3-8-13-23-15-18(17-10-5-7-12-20(17)23)21(24)14-16-9-4-6-11-19(16)22/h4-7,9-12,15H,2-3,8,13-14H2,1H3 Key:YDINKDBAZJOSLV-UHFFFAOYSA-N
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JWH-203 (1-pentyl-3-(2-chlorophenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family that acts as a cannabinoid agonist with approximately equal affinity at both the CB₁ and CB₂ receptors, having a K_i of 8.0 nM at CB₁ and 7.0 nM at CB₂. It was originally discovered by, and named after, John W. Huffman, but has subsequently been sold without his permission as an ingredient of synthetic cannabis smoking blends.^[2] Similar to the related 2'-methoxy compound JWH-250, the 2'-bromo compound JWH-249, and the 2'-methyl compound JWH-251, JWH-203 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds, and has the strongest in vitro binding affinity for the cannabinoid receptors of any compound in the phenylacetyl group.^[3][4][5]

Unexpectedly despite its weaker CB₁ K_i in vitro, the 2-methylindole derivative JWH-204 is actually more potent than JWH-203 in animal tests for cannabinoid activity, though it is still weaker than JWH-249.^[6]

In the United States, JWH-203 is a Schedule I Controlled Substance.^[7]

As of October 2015, JWH-203 is a controlled substance in China.^[8]

• MN-25