JWH-007 is ananalgesic chemical from thenaphthoylindole family, which acts as acannabinoid agonist at both theCB1 andCB2 receptors. It was first reported in 1994 by a group including the noted cannabinoid chemistJohn W. Huffman.[1][2] It was the most active of the first group ofN-alkyl naphoylindoles discovered by the team led by John W Huffman, several years after the family was initially described with the discovery of theN-morpholinylethyl compoundspravadoline (WIN 48,098),JWH-200 (WIN 55,225) andWIN 55,212-2 by theSterling Winthrop group.[3] Several otherN-alkyl substituents were found to be active by Huffman's team including then-butyl,n-hexyl, 2-heptyl, andcyclohexylethyl groups, but it was subsequently determined that the 2-methyl group on theindole ring is not required for CB1 binding, and tends to increase affinity for CB2 instead.[4][5] Consequently, the 2-desmethyl derivative of JWH-007,JWH-018, has slightly higherbinding affinity for CB1, with an optimum binding of 9.00 nM at CB1 and 2.94 nM at CB2, and JWH-007 displayed optimum binding of 9.50 nM at CB1 and 2.94 nM at CB2.[6]
^Huffman JW, Dai D, Martin BR, Compton DR (1994). "Design, Synthesis and Pharmacology of Cannabimimetic Indoles".Bioorganic & Medicinal Chemistry Letters.4 (4):563–566.doi:10.1016/s0960-894x(01)80155-4.
^Pertwee RG, Griffin G, Lainton JA, Huffman JW (September 1995). "Pharmacological characterization of three novel cannabinoid receptor agonists in the mouse isolated vas deferens".European Journal of Pharmacology.284 (3):241–247.doi:10.1016/0014-2999(95)00318-f.PMID8666005.
^Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (December 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.doi:10.1016/S0022-3565(25)10448-5.PMID1335057.
^Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 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.PMID15582455.
^Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes".Current Medicinal Chemistry.12 (12):1395–1411.doi:10.2174/0929867054020864.PMID15974991.
^Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, et al. (August 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.PMID10940540.
^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
