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158240

Sigma-Aldrich

1-Nitrosopyrrolidine

99%

Synonym(s):

N-Nitrosopyrrolidine, NPYR

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About This Item

Empirical Formula (Hill Notation):
C4H8N2O
CAS Number:
930-55-2
Molecular Weight:
100.12
EC Number:
213-218-8
MDL number:
MFCD00003166
UNSPSC Code:
12352200
PubChem Substance ID:
57647525
NACRES:
NA.25

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.

Biochem/physiol Actions

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

208.4 °F - closed cup

Flash Point(C)

98 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Jia Yuan Yang et al.
Journal of hazardous materials, 176(1-3), 602-608 (2009-12-22)
A new route to modify the mesoporous silica MCM-41 with carbon, using the inherent surfactant template in the as-synthesized sample as the carbon precursor, is reported in this article. Apart from the advantage of omitting energy and time required for
Mingyao Wang et al.
Chemical research in toxicology, 20(4), 634-640 (2007-03-31)
N-Nitrosopyrrolidine (NPYR) is a hepatocarcinogen in rats. It is metabolically activated by cytochrome P450 enzymes in the liver leading to the formation of 4-oxobutanediazohydroxide (4) and related intermediates that react with DNA to form adducts. Because DNA adducts are thought
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