JWH-250

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JWH-250
JWH-250.svg
Systematic (IUPAC) name
2-(2-methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone
Clinical data
Legal status Illegal in Czech Republic and Latvia[1]
Identifiers
CAS number 864445-43-2 YesY
ATC code ?
PubChem CID 44397540
ChemSpider 23256117 N
ChEMBL CHEMBL188031 N
Chemical data
Formula C22H25NO2 
Mol. mass 335.439 g/mol
 N (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 Ki 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[edit]

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] An ELISA immunoassay technique for detecting JWH-250 in urine has been reported.[6]

References[edit]

  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. 
  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
  6. ^ Arntson et al (2013) http://jat.oxfordjournals.org/content/37/5/284.abstract