Synthesis and monoamine transporter affinity of new 2β-carbomethoxy-3β-[aryl or heteroaryl]phenyltropanes

Abstract A series of 16 new 2β-carbomethoxy-3β-[aryl or heteroaryl]phenyltropane derivatives was synthesized and evaluated for binding to monoamine transporters. Most of the compounds exhibited nanomolar affinity for the serotonin transporter (SERT). Four compounds ( 29 , 14 , 11 , and 10) presented a particularly attractive pharmacological profile, with very high SERT affinity ( K i 0.15–0.5 nM) and selectivity versus the dopamine transporter of 25- to 77-fold.