JWH-249

JWH-249
Legal status
Legal status	CA: Schedule II ; DE: NpSG (Industrial and scientific use only) ; UK: Under Psychoactive Substances Act ; US: Schedule I ;
Identifiers
	IUPAC name 2-(2-Bromophenyl)-1-(1-pentylindol-3-yl)ethanone;
CAS Number	864445-60-3 ;
PubChem CID	44397335;
ChemSpider	23253217 ;
ChEMBL	ChEMBL363471 ;
CompTox Dashboard (EPA)	DTXSID30658735 ;
Chemical and physical data
Formula	C21H22BrNO
Molar mass	384.317 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCn1cc(c2c1cccc2)C(=O)Cc3ccccc3Br;
	InChI InChI=1S/C21H22BrNO/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:CGQRVOHECAULLB-UHFFFAOYSA-N ;
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JWH-249 (1-pentyl-3-(2-bromophenylacetyl)indole) is a synthetic cannabinoid from the phenylacetylindole family, which acts as a cannabinoid agonist with about 2.4 times selectivity for CB₁ with a K_i of 8.4 ± 1.8 nM and 20 ± 2 nM at CB₂. Similar to the related 2'-methoxy compound JWH-250, the 2'-chloro compound JWH-203, and the 2'-methyl compound JWH-251, JWH-249 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds.[1][2]

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

References

Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR (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.
21 U.S.C. § 812: Schedules of controlled substances

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[1] Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR (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] 21 U.S.C. § 812: Schedules of controlled substances

JWH-249

See also

References