Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors

A series of indole tetrahydropyridine and indole cyclohexenylamines was prepared, and their binding affinities at the human serotonin transporter (SERT) were determined. In particular, compound 6a gave potent SERT activity. The enantiomers of 6a were energy minimized and compared to other known conformationally restricted SSRIs. Compound 6a was also found to give a dose–response similar to the SSRI fluoxetine in microdialysis studies in rats.