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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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Jeong Hyun Heo et al.
Scientific reports, 10(1), 21695-21695 (2020-12-12)
Cholinesterase (ChE) and monoamine oxidase (MAO) inhibitors have been attracted as candidate treatments for Alzheimer's disease (AD). Fifteen khellactone-type coumarins from the roots of Peucedanum japonicum Thunberg were tested for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and MAO inhibitory activities. Compound 3'-angeloyl-4'-(2-methylbutyryl)khellactone
Robert Skibiński et al.
Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society, 26(4), 467-480 (2018-05-31)
Forced degradation of toloxatone in solutions under basic, acidic, neutral, photo UV-VIS, photo UVC and oxidative stress conditions was investigated and structural elucidation of its degradation products was performed with the use of UHPLC system coupled ESI-Q-TOF mass spectrometer. Eight
M L Kaltenbach et al.
Alcoholism, clinical and experimental research, 23(5), 885-890 (1999-06-17)
The pharmacokinetics of toloxatone and ethanol were determined in plasma and cerebrospinal fluid of conscious rabbits. According to a cross-over design, rabbits (n = 5) randomly received on three separate occasions either toloxatone (5 mg/kg), ethanol (1 g/kg), or toloxatone
Seung Cheol Baek et al.
Bioorganic chemistry, 83, 317-325 (2018-11-06)
Three flavanones and two flavones were isolated from the leaves of Prunus padus var. seoulensis by the activity-guided screening for new monoamine oxidase (MAO) inhibitors. Among the compounds isolated, rhamnocitrin (5) was found to potently and selectively inhibit human MAO-A
P Lemoine et al.
Psychopharmacology, 106 Suppl, S118-S119 (1992-01-01)
A double-blind comparison of moclobemide and toloxatone was performed in adult out-patients diagnosed as suffering from a major depressive disorder. Parallel groups of patients received moclobemide, 450 mg/day (n = 135) or toloxatone, 1000 mg/day (n = 133) for 28
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