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M49887

Sigma-Aldrich

1-Methylhydantoin

97%

Synonym(s):

1-Methylimidazolidine-2,4-dione, Dioxy-creatinine, NSC 80560

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About This Item

Empirical Formula (Hill Notation):
C4H6N2O2
CAS Number:
Molecular Weight:
114.10
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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

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

Certificates of Analysis (COA)

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[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)
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
M W Sundberg et al.
Clinical chemistry, 29(4), 645-649 (1983-04-01)
We developed a thin-film enzymic assay for creatinine that makes use of creatinine iminohydrolase (EC 3.5.4.21) to convert creatinine to N-methylhydantoin and ammonia. The ammonia diffuses through a semipermeable layer and is quantitated by reaction with bromphenol blue. A paired
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
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)

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