Imine analogues of tricyclic antidepressants

Analogues of tricyclic antidepressants were synthesized in which the alpha-carbon of the side chain was replaced by nitrogen. The antidepressant activity of these imines, as measured by the reversal of the effects of tetrabenazine in mice, showed a structure-activity relationship similar to that of the carbon analogues. The most active imine (19) was six times as potent as amitriptyline. Some of the compounds differed from amitriptyline in that they produced stimulation in mice.