158240

Sigma-Aldrich

1-Nitrosopyrrolidine

99%

Synonym(s):
NPYR, N-Nitrosopyrrolidine
Empirical Formula (Hill Notation):
C4H8N2O
CAS Number:
Molecular Weight:
100.12
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

99%

refractive index

n20/D 1.489 (lit.)

bp

214 °C (lit.)

density

1.085 g/mL at 25 °C (lit.)

SMILES string

O=NN1CCCC1

InChI

1S/C4H8N2O/c7-5-6-3-1-2-4-6/h1-4H2

InChI key

WNYADZVDBIBLJJ-UHFFFAOYSA-N

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Application

1-Nitrosopyrrolidine can be used to study carcinogens and cancer. Metabolism of nitrosamines in vivo has been tested in rats.1-Nitrosopyrrolidine has been used in a study to assess nitric oxide and spontaneous motility in chick embryos.

Packaging

10 g in glass bottle

Biochem/physiol Actions

Induces hepatocellular carcinomas and lung adenomas in mice. Forms DNA adducts that primarily result in A:T to G:C mutations.

Certificate of Analysis

Certificate of Origin

Mingyao Wang et al.
Chemical research in toxicology, 20(4), 625-633 (2007-03-31)
N-Nitrosopyrrolidine (NPYR) is a well-established hepatocarcinogen in the rat. NPYR requires metabolic activation by cytochrome P450-catalyzed alpha-hydroxylation to express its carcinogenic activity. This produces alpha-hydroxyNPYR (2), which spontaneously ring opens to 4-oxobutanediazohydroxide (4), a highly reactive intermediate, which may itself...
Keita Kanki et al.
Molecular carcinogenesis, 42(1), 9-17 (2004-10-16)
In order to cast light on carcinogen-specific molecular mechanisms underlying experimental hepatocarcinogenesis in rats, in vivo mutagenicity and mutation spectra of known genotoxic rat hepatocarcinogens N-nitrosopyrrolidine (NPYR), and 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), as well as the nongenotoxic hepatocarcinogen di(2-ethylhexyl)phthalate (DEHP) and the...
Nuria Arranz et al.
Journal of applied toxicology : JAT, 26(5), 466-473 (2006-07-28)
The aim of this study was to investigate the protective effect of isothiocyanates towards N-nitrosamine-induced DNA damage in the single-cell gel electrophoresis (SCGE)/HepG2 assay. None of the isothiocyanates (ITCs) concentrations tested in the presence or absence of formamidopyrimidine-DNA glycosylase (Fpg)...
Ana Paula M Loureiro et al.
Chemical research in toxicology, 22(10), 1728-1735 (2009-09-19)
The well established rat hepatocarcinogen N-nitrosopyrrolidine (NPYR, 1) requires metabolic activation to DNA adducts to express its carcinogenic activity. Among the NPYR-DNA adducts that have been identified, the cyclic 7,8-butanoguanine adduct 2-amino-6,7,8,9-tetrahydro-9-hydroxypyrido[2,1-f]purine-4(3H)-one (6) has been quantified using moderately sensitive methods...
M Nakata et al.
Journal of biochemistry, 122(1), 188-192 (1997-07-01)
Aromatic nitroso-compounds such as nitrosobenzene inhibited the respiratory burst of intact neutrophils induced by various stimulants, including phorbol 12-myristate 13-acetate and a chemotactic peptide. The compounds also inhibited NADPH-dependent oxygen consumption by cell-free preparations of neutrophils. This indicates that nitroso-compounds...
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