Pirandamine (AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI).

[1][2][3] It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed.

[1] Pirandamine is structurally related to tandamine, which, in contrast, is a selective norepinephrine reuptake inhibitor.

Acid-catalyzed condensation with ethyl acetoacetate then gives (5).

Reduction with lithium aluminium hydride completes the synthesis of pirandamine (7).