JWH-007

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JWH-007
File:JWH-007 structure.png
Systematic (IUPAC) name
1-pentyl-2-methyl-3-(1-naphthoyl)indole
Clinical data
Legal status
Identifiers
CAS Number 155471-10-6 YesY
PubChem CID: 10360860
ChemSpider 8536309
Chemical data
Formula C25H25NO
Molecular mass 355.471 g/mol
  • c14ccccc4cccc1C(=O)c3c2ccccc2n(c3C)CCCCC
  • InChI=1S/C25H25NO/c1-3-4-9-17-26-18(2)24(22-14-7-8-16-23(22)26)25(27)21-15-10-12-19-11-5-6-13-20(19)21/h5-8,10-16H,3-4,9,17H2,1-2H3
  • Key:IBBNKINXTRKICJ-UHFFFAOYSA-N
  (verify)

JWH-007 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It was the most active of the first group of N-alkyl naphoylindoles discovered by the team led by John W Huffman, several years after the family was initially described with the discovery of the N-morpholinylethyl compounds pravadoline (WIN 48,098), WIN 55,225 (JWH-200) and WIN 55,212-2 by the Sterling Winthrop group.[1] Several other N-alkyl substituents were found to be active by Huffman's team including the n-butyl, n-hexyl, 2-heptyl and cyclohexylethyl groups,[2] but it was subsequently determined that the 2-methyl group on the indole ring is not required for CB1 binding, and tends to increase affinity for CB2 instead.[3][4] Consequently, the 2-desmethyl derivative of JWH-007, JWH-018 has slightly higher binding affinity for CB1, with an optimum binding of 9.00nM at CB1 and 2.94nM at CB2, and JWH-007 displayed optimum binding of 9.50nM at CB1 and 2.94nM at CB2.[5]

Law

JWH-007 was banned in Sweden on 1 October 2010 as a hazardous good harmful to health, after being identified as an ingredient in "herbal" synthetic cannabis products.[6][7]

JWH-007 is illegal in Poland since 08.06.2010 on the basis of 'Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii' published in Dz.U. 2011 nr 105 poz. 614[8]

As of October 2015 JWH-007 is a controlled substance in China.[9]

See also

References

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  2. Huffman JW, Dong D. Design, Synthesis and Pharmacology of Cannabimimetic Indoles. Bioorganic and Medicinal Chemistry Letters. 1994;4(4):563-566.
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  6. Swedish Code of Statutes Regulation (2010:1086).
  7. Swedish Code of Statutes Regulation (2010:1086). (pdf)
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  9. Lua error in package.lua at line 80: module 'strict' not found.


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