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M49887

Sigma-Aldrich

1-Methylhydantoin

97%

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Synonym(s):
1-Methylimidazolidine-2,4-dione, Dioxy-creatinine, NSC 80560
Empirical Formula (Hill Notation):
C4H6N2O2
CAS Number:
616-04-6
Molecular Weight:
114.10
EC Number:
210-460-6
MDL number:
MFCD00003187
PubChem Substance ID:
24896963

Quality Level

200

Assay

97%

mp

156-157 °C (lit.)

SMILES string

CN1CC(=O)NC1=O

InChI

1S/C4H6N2O2/c1-6-2-3(7)5-4(6)8/h2H2,1H3,(H,5,7,8)

InChI key

RHYBFKMFHLPQPH-UHFFFAOYSA-N

Related Categories

Application

Reactant for organocatalytic tandem three component reactions of aldehyde, alkyl vinyl ketone, and amide

Reactant for synthesis of:
  • Selective angiotensin II AT2 receptor agonists with reduced CYP 450 inhibition
  • Allosteric glucokinase activators
  • Hydantoin derivatives with antiproliferative activity
  • Thiohydantoins
  • P2X7 receptor antagonists

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

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K Ienaga et al.
Biochimica et biophysica acta, 967(3), 441-443 (1988-12-15)
The metabolic pathway of 1-methylhydantoin (2) via 5-hydroxy-1-methylhydantoin (3), methylparabanic acid (4) and N5-methyloxaluric acid (5) proved to be a major and general one in mammals. Hence the formation of (3), which has not been detected in normal tissue, is
Bo Yang et al.
Renal failure, 29(8), 1025-1029 (2007-12-11)
1-Methylhydantoin is produced by bacterial creatinine deaminase in the intestinal tract of uremic patients and retaken up into the body. The present study was designed to explore the toxic effect of 1-methylhydantoin on renal proximal tubular cells in vitro. HK-2
[1-Methylhydantoin, an unexpected metabolite of the intelligence-affecting substance dupracetam (author's transl)].
H D Dell et al.
Archiv der Pharmazie, 314(8), 697-702 (1981-08-01)
Hybrid biosensor for clinical and fermentation process control.
I Karube et al.
Annals of the New York Academy of Sciences, 434, 508-511 (1984-01-01)
J M Kim et al.
Biochemical and biophysical research communications, 142(3), 1006-1012 (1987-02-13)
A new enzyme, N-methylhydantoin amidohydrolase, was highly purified from Pseudomonas putida 77: it catalyzes the hydrolysis of N-methylhydantoin to N-carbamoylsarcosine with the concomitant stoichiometric cleavage of ATP to ADP and orthophosphate. The enzyme absolutely requires ATP, MG2+ and K+ for
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