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JWH-249

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 Ki 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]

JWH-249
Legal status
Legal status
Identifiers
  • 2-(2-Bromophenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number
  • 864445-60-3 N
PubChem CID
  • 44397335
ChemSpider
  • 23253217 Y
UNII
  • H988KQV4U9
ChEMBL
  • ChEMBL363471 Y
CompTox Dashboard (EPA)
  • DTXSID30658735
Chemical and physical data
FormulaC21H22BrNO
Molar mass384.317 g·mol−1
3D model (JSmol)
  • Interactive image
  • CCCCCn1cc(c2c1cccc2)C(=O)Cc3ccccc3Br
  • 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 Y
  • Key:CGQRVOHECAULLB-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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

See also edit

References edit

  1. ^ Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, et al. (September 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 (April 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

pentyl, bromophenylacetyl, indole, synthetic, cannabinoid, from, phenylacetylindole, family, which, acts, cannabinoid, agonist, with, about, times, selectivity, with, similar, related, methoxy, compound, chloro, compound, methyl, compound, phenylacetyl, group,. 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 Ki 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 JWH 249Legal statusLegal statusCA Schedule II DE NpSG Industrial and scientific use only UK Under Psychoactive Substances Act US Schedule IIdentifiersIUPAC name 2 2 Bromophenyl 1 1 pentylindol 3 yl ethanoneCAS Number864445 60 3 NPubChem CID44397335ChemSpider23253217 YUNIIH988KQV4U9ChEMBLChEMBL363471 YCompTox Dashboard EPA DTXSID30658735Chemical and physical dataFormulaC 21H 22Br N OMolar mass384 317 g mol 13D model JSmol Interactive imageSMILES CCCCCn1cc c2c1cccc2 C O Cc3ccccc3BrInChI 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 YKey CGQRVOHECAULLB UHFFFAOYSA N Y N Y what is this verify In the United States CB1 receptor agonists of the 3 phenylacetylindole class such as cannabipiperidiethanone are Schedule I Controlled Substances 3 See also editAM 679References edit Huffman JW Szklennik PV Almond A Bushell K Selley DE He H et al September 2005 1 Pentyl 3 phenylacetylindoles a new class of cannabimimetic indoles Bioorganic amp Medicinal Chemistry Letters 15 18 4110 3 doi 10 1016 j bmcl 2005 06 008 PMID 16005223 Manera C Tuccinardi T Martinelli A April 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 nbsp This cannabinoid related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title JWH 249 amp oldid 1132890572, wikipedia, wiki, book, books, library,

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