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N-Nitrosodimethylamine

N-Nitrosodimethylamine
Skeletal formula of N-nitrosodimethylamine
N-Nitrosodimethylamine Ball and Stick.png
N-Nitrosodimethylamine Space Fill.png
Identifiers
62-75-9 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:35807 N
ChEMBL ChEMBL117311 N
ChemSpider 5894 N
ECHA InfoCard 100.000.500
EC Number 200-549-8
KEGG C14704 N
MeSH Dimethylnitrosamine
PubChem 6124
RTECS number IQ0525000
UN number 3382
Properties
C2H6N2O
Molar mass 74.08 g·mol−1
Appearance Yellow, oily liquid
Odor faint, characteristic
Density 1.005 g mL−1
Boiling point 153.1 °C; 307.5 °F; 426.2 K
290 mg mL−1 (at 20 °C)
log P −0.496
Vapor pressure 700 Pa (at 20 °C)
1.437
Thermochemistry
1.65 MJ mol−1
Hazards
Main hazards potential carcinogen
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H301, H330, H350, H372, H411
P260, P273, P284, P301+310, P310
Very Toxic T+ Dangerous for the Environment (Nature) N
R-phrases R45, R25, R26, R48/25, R51/53
S-phrases S45
Flash point 61.0 °C (141.8 °F; 334.1 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
37.0 mg kg−1(oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
OSHA-Regulated Carcinogen
REL (Recommended)
Ca
IDLH (Immediate danger)
Ca [N.D.]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

N-Nitrosodimethylamine (NDMA), also known as dimethylnitrosamine (DMN), is a semi-volatile organic chemical, produced as by-product of several industrial processes and present at very low levels in certain foodstuffs, especially those cooked, smoked, or cured. NDMA is water-soluble, colorless, and its taste and odor are weak or absent. It is toxic to the liver and other organs, and is a suspected human carcinogen.

NDMA is an industrial by-product or waste product of several industrial processes. Manufacturing of unsymmetrical dimethylhydrazine (UDMH), which is a component of rocket fuel that requires NDMA for its synthesis. Of more general concern, water treatment via chlorination or chloramination of organic nitrogen-containing wastewater can lead to the production of NDMA at potentially harmful levels. Further, NDMA can form or be leached during treatment of water by anion exchange resins. Finally, NDMA is found at low levels in numerous items of human consumption including cured meat, fish, beer, and tobacco smoke It is, however, unlikely to bioaccumulate.

N-Nitrosodimethylamine is highly toxic, especially to the liver, and is a suspected human carcinogen. The US Environmental Protection Agency has determined that the maximum admissible concentration of NDMA in drinking water is 0.7 ng L−1. The EPA has not yet set a regulatory maximum contaminant level (MCL) for drinking water. At high doses, it is a "potent hepatotoxin that can cause fibrosis of the liver" in rats. The induction of liver tumors in rats after chronic exposure to low doses is well documented. Its toxic effects on humans are inferred from animal experiments but not well-established experimentally.

NDMA's contamination of drinking water is of particular concern due to the minute concentrations at which it is harmful, the difficulty in detecting it at these concentrations, and to the difficulty in removing it from drinking water. It does not readily biodegrade, adsorb, or volatilize. As such, it cannot be removed by activated carbon and travels easily through soils. Relatively high levels of UV radiation in the 200 to 260 nm range breaks the N-N bond and can thus be used to degrade NDMA. Additionally, reverse osmosis is able to remove approximately 50% of NDMA.


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