STRUCTURE-ACTIVITY RELATIONSHIP STUDIES OF N-SULFONYL ANALOGS OF COCAINE - ROLE OF IONIC INTERACTION IN COCAINE BINDING

Six new N-sulfonylated analogs of cocaine have been prepared, and thes e compounds have been evaluated for their ability to inhibit [H-3]mazi ndol binding and [H-3]dopamine uptake into striatal synaptosomes. The N-sulfonyl compounds still inhibited binding and uptake at low micromo lar concentrations despite the neutral character of the tropane nitrog en, thus suggesting that the binding of cocaine to the dopamine transp orter may not require protonation of its nitrogen and ionic interactio n with its recognition site.