Toloxatone

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]

Toloxatone
Clinical data
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 5-(hydroxymethyl)-3-m-tolyloxazolidin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.045.006
Chemical and physical data
FormulaC11H13NO3
Molar mass207.229 g·mol−1
3D model (JSmol)
  • O=C2OC(CO)CN2c1cccc(c1)C
  • InChI=1S/C11H13NO3/c1-8-3-2-4-9(5-8)12-6-10(7-13)15-11(12)14/h2-5,10,13H,6-7H2,1H3 Y
  • Key:MXUNKHLAEDCYJL-UHFFFAOYSA-N Y

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

References
  1. "Humoryl 200mg gelule 30".
  2. Berlin I, Zimmer R, Thiede HM, et al. (December 1990). "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. doi:10.1111/j.1365-2125.1990.tb05445.x. PMC 1368300. PMID 1705137.
  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, U.S. patent 3,655,687 (1972 to Delalande Sa).
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