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Merck
CN

N5154

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
UNSPSC Code:
12352202
PubChem Substance ID:
24897723
EC Number:
213-258-6
MDL number:
MFCD00467141

Key Documents

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InChI key

UZMVSVHUTOAPTD-UHFFFAOYSA-N

InChI

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

SMILES string

O=NN1CCCCCC1

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

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

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
065H0388

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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
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
L I Hecker et al.
Teratogenesis, carcinogenesis, and mutagenesis, 3(1), 9-17 (1983-01-01)
There is a direct relationship between the metabolism and mutagenicity of N-nitrosohexamethyleneimine (NO-HEX) in the presence of uninduced and AC- and PB-induced S8 and S9 fractions from rats and hamsters. Although alpha-hydroxylation is the most important process in the formation
G M Singer et al.
IARC scientific publications, (57)(57), 459-463 (1984-01-01)
We have studied the urinary metabolites of N-nitrosopiperidine, 3- and 4-hydroxy-N-nitrosopiperidine, N-nitroso-4-piperidone, N-nitrosohexamethyleneimine and N-nitroso-heptamethyleneimine. The N-nitrosopiperidines induce primarily oesophageal tumours in rats; N-nitrosohexamethyleneimine induces oesophageal and liver tumours and N-nitrosoheptamethyleneimine induces oesophageal and lung tumours. The products were identified
L I Hecker et al.
Chemico-biological interactions, 49(1-2), 235-248 (1984-04-01)
The formation of the products of microsomal metabolism of the cyclic nitrosamine, nitrosohexamethyleneimine (NO-HEX) were studied. Information on the origins of the oxygen atoms in four major metabolites of NO-HEX was obtained by metabolizing this compound in an 18O2 atmosphere
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