Jwh-007

JWH-007

Systematic (IUPAC) name
1-pentyl-2-methyl-3-(1-naphthoyl)indole
Clinical data
Legal status	?
Identifiers
CAS number	Y
ATC code	?
PubChem
ChemSpider
Chemical data
Formula	C25H25NO
Mol. mass	355.471 g/mol
SMILES c14ccccc4cccc1C(=O)c3c2ccccc2n(c3C)CCCCC
InChI 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
Y

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

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

• JWH-015
• JWH-018
• JWH-019
• JWH-073

References

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.  
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.  
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.  
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.  
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.