Toloxatone

Toloxatone is an antidepressant launched in 1984 in France by Sanofi Aventis for the treatment of Major [depressive disorder|depression]. It was discontinued in 2002. It acts as a selective reversible inhibitor of [monoamine oxidase A|reversible inhibitor of MAO-A].

Synthesis

The reaction between glycidol and m-toluidine gives 3-m-toluidinopropane-1,2-diol. Treatment with diethyl carbonate in the presence of sodium methoxide leads to an intermolecular cycloaddition to give tomoxatone.