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Merck

N0756

N-Nitrosodiethylamine

liquid, nitrosamine

Synonym(s):

Diethylnitrosamine

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About This Item

Linear Formula:
(C2H5)2NNO
CAS Number:
55-18-5
Molecular Weight:
102.14
NACRES:
NA.77
PubChem Substance ID:
24897440
UNSPSC Code:
12352116
EC Number:
200-226-1
MDL number:
MFCD00013890
Beilstein/REAXYS Number:
1744991

Product Name

N-Nitrosodiethylamine, liquid

InChI key

WBNQDOYYEUMPFS-UHFFFAOYSA-N

InChI

1S/C4H10N2O/c1-3-6(4-2)5-7/h3-4H2,1-2H3

SMILES string

CCN(CC)N=O

form

liquid

color

yellow

bp

177 °C (lit.)

density

0.95 g/mL (lit.)

Quality Level

100

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Application

N-Nitrosodiethylamine has been used to induce hepatocarcinogenesis in rat and mice.

Biochem/physiol Actions

N-Nitrosodiethylamine (NDMA) is carcinogenic in all animal species tested. The main target organs are the nasal cavity, trachea, lung, esophagus and liver. NDMA is acted upon by the cytochrome P450 system resulting in the formation of carcinogenic methyldiazonium ion. However microbes like Pseudomonas metabolize NDMA into N-nitromethylamine (NTMA) and formaldehyde.

General description

N-Nitrosodiethylamine belongs to the nitrosamines category of nitrogenous disinfection byproduct. It is also generated in chlorine based water treatment plants.

Packaging

Bulk Package

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 3 - Carc. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
049K1613V
049K1613
078K1635
018K1369
087K1460

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Effects of heavy metal ions on N-nitrosodimethylamine (NDMA) formation
Liu Y, et al.
Royal Society of Chemistry Advances, 6(74), 70474-70479 (2016)
Smyd3 is a transcriptional potentiator of multiple cancer-promoting genes and required for liver and colon cancer development
Sarris ME, et al.
Cancer Cell, 29(3), 354-366 (2016)
Jun Ho Lee et al.
EBioMedicine, 58, 102926-102926 (2020-08-03)
High recurrence and chemoresistance drive the high mortality in hepatocellular carcinoma (HCC). Although cancer stem cells are considered to be the source of recurrent and chemoresistant tumors, they remain poorly defined in HCC. Tonicity-responsive enhancer binding protein (TonEBP) is elevated
Occurrence and control of N-nitrosodimethylamine in water engineering systems
Bian Y, et al.
Environmental Engineering Research, 24(1), 1-16 (2018)
Diane Fournier et al.
Applied and environmental microbiology, 72(10), 6693-6698 (2006-09-05)
N-Nitrosodimethylamine (NDMA) is a potent carcinogen and an emerging contaminant in groundwater and drinking water. The metabolism of NDMA in mammalian cells has been widely studied, but little information is available concerning the microbial transformation of this compound. The objective
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