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T3452

Sigma-Aldrich

Toloxatone

≥98% (HPLC), solid

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C11H13NO3
Número de CAS:
29218-27-7
Peso molecular:
207.23
EC Number:
249-522-2
MDL number:
MFCD00865391
UNSPSC Code:
12161501
PubChem Substance ID:
329826767
NACRES:
NA.77

Quality Level

100

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

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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
Geum Seok Jeong et al.
Molecules (Basel, Switzerland), 25(17) (2020-08-30)
Eight compounds were isolated from the roots of Glycyrrhiza uralensis and tested for cholinesterase (ChE) and monoamine oxidase (MAO) inhibitory activities. The coumarin glycyrol (GC) effectively inhibited butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) with IC50 values of 7.22 and 14.77 µM
S Vajta et al.
Journal of chromatography, 311(2), 329-337 (1984-11-28)
A method for the analytical and micropreparative separation of toloxatone and its urinary metabolites in man is described. Toloxatone was given as an aqueous solution and was labelled with 14C. Following solvent extraction of urine, before and after enzymatic hydrolysis
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