(11E)-11-[3-(dimethylamino)propylidene]-6H-benzo[c][1]benzothiepine-2-carbonitrile

Cyanodothiepin (developmental code name BTS-56,424) is a tricyclic antidepressant (TCA) acting as a potent and highly selective (over norepinephrine and dopamine uptake) inhibitor of the reuptake of serotonin that was never marketed. It also has moderate affinity for the mACh receptors and weak/negligible affinity for the α1-adrenergic, 5-HT2A, D1, and D2 receptors; the H1 receptor has not been assayed, but cyanodothiepin is less sedating than the related drug cianopramine, suggesting its antihistamine activity is not as pronounced as other TCAs. Cyanodothiepin is active in the forced swimming test (FST), inferring that it may possess antidepressant properties in humans. However, it is only weakly active compared to cianopramine and imipramine in monoamine depletion-based tests of antidepressant potential.