|AHFS/Drugs.com||Consumer Drug Information|
|By mouth (tablets)|
|Elimination half-life||1.5 hours|
|Excretion||Minor, renal and fecal|
|Chemical and physical data|
|Molar mass||276.374 g/mol|
|3D model (JSmol)|
Molindone, sold under the brand name Moban, is an antipsychotic which is used in the United States in the treatment of schizophrenia. It works by blocking the effects of dopamine in the brain, leading to diminished psychoses. It is rapidly absorbed when taken orally.
Molindone was discontinued by its previous supplier, Endo Pharmaceuticals, on January 13, 2010. It is currently available in the U.S. from CorePharma under Abbreviated New Drug Application approved March 23, 2015.
Condensation of oximinoketone 2 (from nitrosation of 3-pentanone), with cyclohexane-1,3-dione (1) in the presence of zinc and acetic acid leads directly to the partly reduced indole derivative 6. The transformation may be rationalized by assuming as the first step, reduction of 2 to the corresponding α-aminoketone. Conjugate addition of the amine to 1 followed by elimination of hydroxide (as water) would give ene-aminoketone 3. This enamine may be assumed to be in tautomeric equilibrium with imine 4. Aldol condensation of the side chain carbonyl group with the doubly activated ring methylene group would then result in cyclization to pyrrole 5; simple tautomeric transformation would then give the observed product. Mannich reaction of 6 with formaldehyde and morpholine gives the tranquilizer molindone (7).
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