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pubmed-article:9632375pubmed:abstractTextAll four stereoisomers of (+/-)-2-(methoxycarbonyl)-7-methyl-3-phenyl-7-azabicyclo[2.2. 1]heptane were synthesized and evaluated as cocaine binding site ligands at the dopamine transporter. The in vitro binding affinities (Ki) of the 7-azabicyclo[2.2.1]heptane derivatives were measured in rat caudate-putamen tissue and found to be 100-3000-fold less potent (Ki = 5-96 microM) than cocaine and 2beta-(methoxycarbonyl)-3beta-phenyltropane (2, WIN 35,065-2). Surprisingly, the 3alpha-phenyl isomers (6c, 6d) were more potent than the 3beta-phenyl isomers (6a, 6b). Molecular modeling studies revealed that the rigid 7-azabicyclo[2.2.1]heptane derivatives possess molecular topologies which are significantly different than the molecular topologies of the 2beta-(methoxycarbonyl)-3-phenyltropanes.lld:pubmed
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pubmed-article:9632375pubmed:articleTitleSynthesis and dopamine transporter affinity of the four stereoisomers of (+/-)-2-(methoxycarbonyl)-7-methyl-3-phenyl-7-azabicyclo[2.2.1]heptane.lld:pubmed
pubmed-article:9632375pubmed:affiliationDepartment of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA.lld:pubmed
pubmed-article:9632375pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:9632375pubmed:publicationTypeComparative Studylld:pubmed
pubmed-article:9632375pubmed:publicationTypeResearch Support, U.S. Gov't, P.H.S.lld:pubmed
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