Novel conformationally restricted tetracyclic analogs of delta8-tetrahydrocannabinol

Bioorg Med Chem Lett. 1999 Aug 2;9(15):2119-24. doi: 10.1016/s0960-894x(99)00355-8.

Abstract

Novel analogs of (-)-delta8-tetrahydrocannabinol (delta8-THC) in which the conformation of the side chain was restricted by incorporating the first one or two carbons into a six membered ring fused with the aromatic phenolic A ring were synthesized. The affinities of the novel ligands for CB1 and CB2 indicated that the "southbound" chain conformer retained the highest affinity for both receptors.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Brain / metabolism
  • Cell Membrane / drug effects
  • Cell Membrane / metabolism
  • Dronabinol / analogs & derivatives*
  • Dronabinol / chemical synthesis
  • Dronabinol / chemistry
  • Dronabinol / metabolism
  • Mice
  • Rats
  • Receptor, Cannabinoid, CB2*
  • Receptors, Cannabinoid
  • Receptors, Drug / drug effects
  • Receptors, Drug / metabolism
  • Spleen / metabolism
  • Structure-Activity Relationship

Substances

  • Cnr2 protein, rat
  • Receptor, Cannabinoid, CB2
  • Receptors, Cannabinoid
  • Receptors, Drug
  • delta-8-tetrahydrocannabinol
  • Dronabinol