Mesoridazine

 ( M1 Receptor Antagonists ) 

Mesoridazine ( Serentil) is a phenothiazine class drug that is used in the treatment of schizophrenia. It is one of the active metabolites of thioridazine. The drug's name is derived from the methyl sulf oxy and pipe ridine functional groups in its chemical structure.

It has central antiadrenergic, antidopaminergic, antiserotonergic and weak muscarinic anticholinergic effects.

Serious side effects include akathisia, tardive dyskinesia and the potentially fatal neuroleptic malignant syndrome.

Mesoridazine was withdrawn from the United States market in 2004 due to dangerous side effects, namely irregular heart beat and QT-prolongation of the electrocardiogram.

Mesoridazine is on the FDA's Discontinued Drug Product List.

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Synthesis 2-Methylthiophenothiazine 7643-08-5 ( 1) is treated with acetic anhydride] to give the protected amide, ie 10-acetyl-2-methylthiophenothiazine, CID:69367526. Oxidation of this by means of hydrogen peroxide and removal of the acetyl protecting group with potassium carbonate in methanol solution gives 2-methylsulfonylphenothiazine 23503-68-6 ( 3). Introduction of the sidechain by alkylation with 2-(2-chlorethyl)-1-methylpiperidine 50846-01-0 ( 6) in the presence of sodamide, afforded the desired mesoridazine ( 5).

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