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	N06AG03 (WHO)
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 5-(hydroxymethyl)-3-m-tolyloxazolidin-2-one
CAS Number	29218-27-7 Y
PubChem CID	34521
ChemSpider	31769 Y
UNII	5T206015T5
KEGG	D02559 Y
ChEBI	CHEBI:134870
ChEMBL	ChEMBL18116 Y
CompTox Dashboard (EPA)	DTXSID40865478
ECHA InfoCard	100.045.006
Chemical and physical data
Formula	C11H13NO3
Molar mass	207.229 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C2OC(CO)CN2c1cccc(c1)C
InChI 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

• Befloxatone
• Cimoxatone