Benzyl cation inititiated intramolecular cyclization reactions with co
njugated C-C double bonds were performed providing rac. endo-exo isome
rs of 1-azabicyclo[3.2.1] octenes (2 and 3). Formation of the endo iso
mer 2 is favoured. Compounds 2 possess dopamine uptake inhibitory effe
ct with an additional selective MAO-B enzyme inhibitory potential. The
remarkable in vitro effects do not correspond to in viva antidepressa
nt activity.