Toloxatone Explained

Toloxatone (Humoryl) is an antidepressant launched in 1984 in France by Sanofi Aventis for the treatment of depression. It was discontinued in 2002.^[1] It acts as a selective reversible inhibitor of MAO-A (RIMA).^[2]

Synthesis

The reaction between glycidol (1) and m-toluidine (2) gives 3-m-toluidinopropane-1,2-diol (3). Treatment with diethyl carbonate (4) in the presence of sodium methoxide leads to an intermolecular cycloaddition to give tomoxatone.^{[3] [4] [5]}

See also

• Befloxatone
• Cimoxatone

Notes and References

1. Web site: Humoryl 200mg gelule 30.
2. Berlin I, Zimmer R, Thiede HM, etal . Comparison of the monoamine oxidase inhibiting properties of two reversible and selective monoamine oxidase-A inhibitors moclobemide and toloxatone, and assessment of their effect on psychometric performance in healthy subjects . British Journal of Clinical Pharmacology . 30 . 6 . 805–16 . December 1990 . 1705137 . 1368300 . 10.1111/j.1365-2125.1990.tb05445.x.
3. Sungurbey, K .; Castaer, J .; Toloxatone. Drugs Fut 1976, 1, 12, 569.
4. Douzon, C.; Fauvan, C.; Une nouvelle serie d'antidpresseurs: les derivs de l'hydroxymthyl-5-oxazolidinone-2. Chimie Thrapeutique 1973, 3, 324-327.
5. DE2012120 Claude P Fauran, Guy M Raynaud, Rene A Oliver, Colette A Douzon, (1972 to Delalande Sa).