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T3452

Sigma-Aldrich

Toloxatone

≥98% (HPLC), solid

Synonym(s):

5-(Hydroxymethyl)-3-(3-methylphenyl)-2-oxazolidinone, Humoryl

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About This Item

Empirical Formula (Hill Notation):
C11H13NO3
CAS Number:
29218-27-7
Molecular Weight:
207.23
EC Number:
249-522-2
MDL number:
MFCD00865391
UNSPSC Code:
12161501
PubChem Substance ID:
329826767
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

Cc1cccc(c1)N2CC(CO)OC2=O

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

InChI key

MXUNKHLAEDCYJL-UHFFFAOYSA-N

Biochem/physiol Actions

Toloxatone is a reversible monoamine oxidase A inhibitor (MAOI) and antidepressant. Toloxatone belongs to the aryloxazolidinones, a relatively new class of reversible monoamine oxidase A inhibitors (MAOI). Studies show that derivatives such as 3-aryloxazolidin-2-one (oxazolidinones), which are regularly used to treat gram positive infections, represent a new class of reversible as well as irreversible inhibitors for MAO-A and MAO-B enzymes that are able to inhibit protein synthesis and also used for neurodegenerative-type pathologies.

Preparation Note

Toloxatone is soluble in DMSO at a concentration that is greater than 10 mg/ml.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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B Mallesham et al.
Organic letters, 5(7), 963-965 (2003-03-28)
[reaction: see text] Coupling of a variety of substituted aryl bromides with oxazolidinones has been achieved using the Buchwald protocol for the amidation of aryl halides. This procedure is exemplified by the synthesis of two medicinally important molecules, linezolid and
M Strolin Benedetti et al.
Naunyn-Schmiedeberg's archives of pharmacology, 323(4), 315-320 (1983-08-01)
In both rat brain and heart, noradrenaline and 5-hydroxytryptamine are metabolised predominantly by monoamine oxidase-A. The Km values for 14C-noradrenaline in the rat brain and heart are 290 microM and 300 microM, respectively, whereas for 14C-5-hydroxytryptamine the values are 180
Roberto Di Santo et al.
Journal of medicinal chemistry, 48(13), 4220-4223 (2005-06-25)
Pyrrolylethanoneamines 1-12, 18-23 and related amino alcohols 13-15, 24-27 were synthesized and tested against monoamine oxidases A and B (MAO-A and MAO-B) enzymes. In general, aminoketones 1-12, 18-23 were found to be potent and selective MAO-A inhibitors. In particular, 18
I Berlin et al.
British journal of clinical pharmacology, 30(6), 805-816 (1990-12-01)
1. The effects of two reversible, predominantly monoamine oxidase-A (MAO-A) inhibitors, moclobemide (150 mg three times daily) and toloxatone (400-200-400 mg day-1) on monoamine metabolites and psychometric performance were compared in a double-blind placebo controlled crossover study in 12 healthy
D Pateron et al.
Gastroenterologie clinique et biologique, 14(5), 504-506 (1990-01-01)
We report two cases of fulminant hepatitis which might be due to toloxatone, a new type-A monoamine oxidase inhibitor. Hepatitis occurred 20 days after the beginning of toloxatone administration in the first case and 138 days after the reintroduction of
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