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N5154

Sigma-Aldrich

N-Nitrosohexamethyleneimine

Synonym(s):

Hexahydro-1-nitrosoazepine

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About This Item

Empirical Formula (Hill Notation):
C6H12N2O
CAS Number:
932-83-2
Molecular Weight:
128.17
EC Number:
213-258-6
MDL number:
MFCD00467141
UNSPSC Code:
12352202
PubChem Substance ID:
24897723

form

liquid

refractive index

n20/D 1.497 (lit.)

bp

233 °C (lit.)

density

1.06 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

O=NN1CCCCCC1

InChI

1S/C6H12N2O/c9-7-8-5-3-1-2-4-6-8/h1-6H2

InChI key

UZMVSVHUTOAPTD-UHFFFAOYSA-N

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Biochem/physiol Actions

Mutagenic and carcinogenic. A trace-enrichment HPLC method has been developed for quantitating this compound as an impurity (to ppb levels) in tolazamide, and potentially other pharmaceutical preparations.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk_germany

WGK 3

flash_point_f

210.2 °F - closed cup

flash_point_c

99 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
065H0388

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C M Goodall et al.
Toxicology, 33(3-4), 251-259 (1984-12-01)
The carcinogenic response of NZO/BlGd inbred mice of both sexes to oral N-nitrosohexamethyleneimine (NHEX) was investigated at 2 differing dose rates, but equal cumulative doses. Mice received 52 mg NHEX (2 mg/g body wt) in drinking water over either an
C M Goodall et al.
Journal of the National Cancer Institute, 73(5), 1215-1218 (1984-11-01)
The carcinogenic activity of N-nitrosohexamethyleneimine [(NHEX) CAS: 932-83-2; hexahydro-1-nitroso-1H-azepine] was studied in male and female mice of the four inbred strains NZB/BlGd, NZC/BlGd, NZO/BlGd, and NZY/BlGd. A total of 158 mice received NHEX treatment; 1,338 untreated controls were used, all
L I Hecker et al.
Cancer research, 42(1), 59-64 (1982-01-01)
The in vitro metabolism of N-nitrosohexamethyleneimine by lung and liver microsomes and cytosol from uninduced male Fischer rats is described. Metabolites produced by both organs appeared to be identical. The liver subcellular fractions had a lower Km (0.6 mM) than
A E Ross et al.
Cancer letters, 15(3), 329-334 (1982-03-01)
Liver DNA and RNA were isolated from rats treated with the liver carcinogens N-nitrosopyrrolidine (NPYR) and N-nitrosohexamethyleneimine (NHX). After hydrolysis in 70% perchloric acid (100 degrees C, 1.0 h), 70% of the radioactivity in both the DNA and RNA hydrolysates
G W Harrington et al.
Cancer letters, 32(2), 187-191 (1986-08-01)
Tolazamide, an antidiabetic drug, was found to produce N-nitrosohexamethyleneimine (NHM) upon exposure to an oxidizing agent and in the absence of a nitrosating agent. The oxidizing agents were either hydrogen peroxide or oxygen.
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