Ciclazindol

Ciclazindol (WY-23,409) is an antidepressant and anorectic drug of the tetracyclic chemical class that was developed in the mid to late 1970s, but was never marketed. It acts as a norepinephrine reuptake inhibitor, and to a lesser extent as a dopamine reuptake inhibitor. Ciclazindol has no effects on the SERT, 5-HT receptors, mACh receptors, or α-adrenergic receptors, and has only weak affinity for the H₁ receptor. As suggested by its local anesthetic properties, ciclazindol may also inhibit sodium channels. It is known to block potassium channels as well.

Synthesis

Ciclazindol can be synthesized from isitin (1). Reaction with 2-chlorophenylmagnesium bromide thus gives 2. Conjugate addition of the anion of that product to acrylonitrile affords the propionitrile 3. The cyano group is then reduced to the primary amine by means of lithium aluminum hydride. Internal imine formation leads to cyclization to form ciclazindol.

See also

References