JWH-007

From Wikipedia, the free encyclopedia
Jump to: navigation, search
JWH-007
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
ATC code ?
PubChem CID 10360860
ChemSpider 8536309
Chemical data
Formula C25H25NO 
Mol. mass 355.471 g/mol
 YesY (what is this?)  (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[edit]

Sweden: 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] Poland: 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]

See also[edit]

References[edit]

  1. ^ Compton, D. R., et al. (1992). "Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol". The Journal of Pharmacology and Experimental Therapeutics 263 (3): 1118–1126. PMID 1335057.   edit
  2. ^ Huffman JW, Dong D. Design, Synthesis and Pharmacology of Cannabimimetic Indoles. Bioorganic and Medicinal Chemistry Letters. 1994;4(4):563-566.
  3. ^ Huffman, J., et al. (2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists.". Bioorganic & Medicinal Chemistry 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.   edit
  4. ^ Huffman, J. W.; Padgett, L. W. (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current medicinal chemistry 12 (12): 1395–1411. doi:10.2174/0929867054020864. PMID 15974991.  edit
  5. ^ Aung, M. M., et al. (2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding". Drug and alcohol dependence 60 (2): 133–140. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.   edit
  6. ^ Swedish Code of Statutes Regulation (2010:1086).
  7. ^ Swedish Code of Statutes Regulation (2010:1086). (pdf)
  8. ^ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". ISAP. Retrieved 12 June 2011.