Synthesis and monoamine transporter affinity of 3-aryl substituted trop-2-enes

A series of new 3-aryl-tropanes have been synthesized, and their affinities and selectivities were evaluated for monoamine transporters. (1RS)-3-(Fluoren-2-yl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene exhibited the highest affinity for the human serotonin transporter (IC50 = 14.5 nM). It is also 52-fold and 230-fold selective over human dopamine and norepinephrine transporters, respectively.