Minaprine
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Minaprine (INN, USAN, BAN; brand names Brantur, Cantor) is a monoamine oxidase inhibitor antidepressant drug that was used in France for the treatment of depression until it was withdrawn from the market in 1996 because it caused convulsions.[1][2]
A study found that it acts as a reversible inhibitor of MAO-A (RIMA) in rats.[3] It has also been found to weakly inhibit acetylcholinesterase in rat brain (striatum) homogenates.[4]
It has demonstrated significant antibiotic activity against M. chelonae and M. abscessus in tests with antibiotic resistant bacteria.[5]
Synthesis
The first synthesis of minaprine was disclosed in patents published in 1979.[6]
The final step is the reaction between a chloro-substituted pyridazine and the primary amine group of a morpholine derivative.[6][7] The required pyridazine can be made by the reaction of acetophenone and pyruvic acid, followed by ring formation using hydrazine, giving a pyrazidinone. Treatment of this with phosphoryl chloride converts it to the required chloro derivative.[1]
References
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