Synthesis and ligand binding of cocaine isomers at the cocaine receptor
Carroll, F., Lewin, A., Abraham, P., Parham, K., Boja, J. W., & Kuhar, M. J. (1991). Synthesis and ligand binding of cocaine isomers at the cocaine receptor. Journal of Medicinal Chemistry, 34(3), 883-886.
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