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JWH-007

Chemical compound

Chemical compound

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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 first reported in 1994 by a group including the noted cannabinoid chemist John W. Huffman. 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), JWH-200 (WIN 55,225) and WIN 55,212-2 by the Sterling Winthrop group. 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, 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. Consequently, the 2-desmethyl derivative of JWH-007, JWH-018, has slightly higher binding 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.

References

References

  1. (1994). "Design, Synthesis and Pharmacology of Cannabimimetic Indoles". Bioorganic & Medicinal Chemistry Letters.
  2. (September 1995). "Pharmacological characterization of three novel cannabinoid receptor agonists in the mouse isolated vas deferens". European Journal of Pharmacology.
  3. (December 1992). "Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol". The Journal of Pharmacology and Experimental Therapeutics.
  4. (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.
  5. (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry.
  6. (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.
  7. {{UnitedStatesCode2. 21. 812. Schedules of controlled substances
  8. [http://www.riksdagen.se/webbnav/index.aspx?nid=3911&bet=1999:58 Swedish Code of Statutes Regulation (2010:1086).]
  9. "Swedish Code of Statutes Regulation (2010:1086). (pdf)".
  10. "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". ISAP.
  11. (27 September 2015). "关于印发《非药用类麻醉药品和精神药品列管办法》的通知". China Food and Drug Administration.
  12. "Stoffe gem. Anlagen zum BtMG".
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designer-drugs jwh-cannabinoids naphthoylindoles cb1-receptor-agonists cb2-receptor-agonists
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