Synthesis and ligand binding of cocaine isomers at the cocaine receptor

J Med Chem. 1991 Mar;34(3):883-6. doi: 10.1021/jm00107a003.

Abstract

The cocaine binding site at the dopamine transporter has been found to be stereoselective. Thus, the seven possible stereoisomers of (-)-cocaine have been synthesized and found to inhibit [3H]-2 beta-carbomethoxy-3 beta-(4-fluoro-phenyl)tropane [( 3H]WIN 35,428) with potencies ranging from 1/60 to 1/600 of that of (-)-cocaine. The synthesis and characterization of all new compounds is presented.

Publication types

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

MeSH terms

  • Animals
  • Binding, Competitive
  • Carrier Proteins*
  • Cell Membrane / metabolism
  • Chemical Phenomena
  • Chemistry
  • Cocaine / analogs & derivatives
  • Cocaine / chemical synthesis*
  • Cocaine / chemistry
  • Cocaine / metabolism
  • Corpus Striatum / metabolism
  • Male
  • Molecular Structure
  • Rats
  • Rats, Inbred Strains
  • Receptors, Drug / metabolism*
  • Stereoisomerism

Substances

  • Carrier Proteins
  • Receptors, Drug
  • cocaine receptor
  • (1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester
  • Cocaine