Enantioselective synthesis and pharmacology of 11-hydroxy-(1'S,2'R)-dimethylheptyl-delta 8-THC

Bioorg Med Chem Lett. 1998 Aug 18;8(16):2223-6. doi: 10.1016/s0960-894x(98)00385-0.

Abstract

An enantioselective synthesis of the (1'S,2'R)-dimethylheptyl cannabinoid side chain has been developed and employed in the synthesis of 11-hydroxy-(1'S,2'R)-dimethylheptyl-delta 8-THC (3). Pharmacology, in vivo and in vitro, indicate (3) to be one of the most potent traditional cannabinoids known.

Publication types

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

MeSH terms

  • Animals
  • Binding, Competitive
  • Brain / metabolism
  • Cannabinoids / pharmacokinetics
  • Cell Membrane / metabolism
  • Cyclohexanols / pharmacokinetics
  • Dronabinol / analogs & derivatives*
  • Dronabinol / chemistry
  • Indicators and Reagents
  • Kinetics
  • Mice
  • Molecular Structure
  • Receptors, Cannabinoid
  • Receptors, Drug / drug effects
  • Receptors, Drug / metabolism*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Cannabinoids
  • Cyclohexanols
  • Indicators and Reagents
  • Receptors, Cannabinoid
  • Receptors, Drug
  • Dronabinol
  • 3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol