JWH-250

JWH-250
Legal status
Legal status	Illegal in Czech Republic and Latvia;
Identifiers
	IUPAC name 2-(2-methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone;
CAS Number	864445-43-2 ;
PubChem CID	44397540;
ChEMBL	ChEMBL188031 ;
CompTox Dashboard (EPA)	DTXSID40235556 ;
Chemical and physical data
Formula	C22H25NO2
Molar mass	335.439 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc2ccccc2CC(=O)c(c3ccccc13)cn1CCCCC;
	(what is this?) (verify)

JWH-250 or (1-pentyl-3-(2-methoxyphenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family that acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors, with a K_i of 11nM at CB₁ and 33nM at CB₂. Unlike many of the older JWH series compounds, this compound does not have a naphthalene ring, instead occupying this position with a 2'-methoxy-phenylacetyl group, making JWH-250 a representative member of a new class of cannabinoid ligands.^[2] Other 2'-substituted analogues such as the methyl, chloro and bromo compounds are also active and somewhat more potent.^[3]^[4]

History

JWH-250 was discovered by, and named after the researcher Dr. John W. Huffman. He created JWH-250 and a number of other compounds to research the structure and function of the endocannabinoid system of mammals. Samples of JWH-250 were first identified in May 2009 by the German Federal Criminal Police, as an ingredient in new generation "herbal smoking blends" that had been released since the banning of the original ingredients (C8)-CP 47,497 and JWH-018.^[5]

References

^ Legal article in Latvian (www.likumi.lv)
^ 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. {{cite journal}}: Explicit use of et al. in: |first= (help)
^ 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.
^ The Cannabinoid Receptors. Edited by Patricia H Reggio. Humana Press 2009. ISBN 978-1-58829-712-9
^ Understanding the ‘Spice’ phenomenon. EMCDDA, Lisbon, November 2009

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[1] Legal article in Latvian (www.likumi.lv)

[2] 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. {{cite journal}}: Explicit use of et al. in: |first= (help)

[3] 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.

[4] The Cannabinoid Receptors. Edited by Patricia H Reggio. Humana Press 2009. ISBN 978-1-58829-712-9

[5] Understanding the ‘Spice’ phenomenon. EMCDDA, Lisbon, November 2009

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