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Sigma-Aldrich

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:
1121-07-9
Molecular Weight:
113.11
MDL number:
MFCD00005517
UNSPSC Code:
12352100
PubChem Substance ID:
24859505
NACRES:
NA.22

assay

99%

form

solid

bp

234-235 °C (lit.)

mp

61-70 °C (lit.)

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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

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