title: Synthesis and ligand binding of cocaine isomers at the cocaine receptor.
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.
authors.affiliation: Chemistry and Life Sciences, Research Triangle Institute, North Carolina 27709.
authors.forename: F I
authors.initials: FI
authors.lastname: Carroll
authors.forename: A H
authors.initials: AH
authors.lastname: Lewin
authors.forename: P
authors.initials: P
authors.lastname: Abraham
authors.forename: K
authors.initials: K
authors.lastname: Parham
authors.forename: J W
authors.initials: JW
authors.lastname: Boja
authors.forename: M J
authors.initials: MJ
authors.lastname: Kuhar
mesh_terms: D000818:Animals; D001667:Binding, Competitive; D002352:Carrier Proteins; D002462:Cell Membrane / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D003042:Cocaine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D003342:Corpus Striatum / Q000378:metabolism; D008297:Male; D015394:Molecular Structure; D051381:Rats; D011919:Rats, Inbred Strains; D011955:Receptors, Drug / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D002352:Carrier Proteins; D011955:Receptors, Drug; C061445:cocaine receptor; C021279:(1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester; D003042:Cocaine