325384
N-Methylsuccinimide
99%
Synonym(s):
1-Methyl-2,5-pyrrolidinedione, N-Methyl-2,5-pyrrolidinedione
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About This Item
Empirical Formula (Hill Notation):
C5H7NO2
CAS Number:
Molecular Weight:
113.11
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
99%
form
solid
bp
234-235 °C (lit.)
mp
61-70 °C (lit.)
functional group
imide
SMILES string
CN1C(=O)CCC1=O
InChI
1S/C5H7NO2/c1-6-4(7)2-3-5(6)8/h2-3H2,1H3
InChI key
KYEACNNYFNZCST-UHFFFAOYSA-N
General description
N-Methylsuccinimide is a metabolite of N-methyl-2-pyrrolidone (NMP) and its presence in in plasma and urine can be used as a biomarker of exposure to NMP. Hydrogen bonded complexes between N-methylsuccinimide and phenols (pKa = 10.2 → 6) are investigated by infrared spectrometry.
Application
N-Methylsuccinimide was employed as model compound to investigate the mechanism of enolization step by density-functional theory (DFT) calculations.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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nfrared Study of the Hydrogen Bond Complexes Between N-Methylsuccinimide and Phenols.
Bruyneel K, et al.
Spectroscopy Letters, 29(4), 739-747 (1996)
Ohgi Takahashi et al.
Chemistry & biodiversity, 7(6), 1349-1356 (2010-06-22)
Racemization of aspartic acid residues in peptides and proteins is assumed to proceed via succinimide intermediates. An enolization of the succinimide intermediate is required for the racemization to occur. In this study, we modeled the enolization step by density-functional theory
N-Methylsuccinimide in plasma and urine as a biomarker of exposure to N-methyl-2-pyrrolidone.
Jonsson BAG and ?kesson B.
International Archives of Occupational and Environmental Health, 74(4), 289-294 (2004)
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