ContaminantDB: N-Nitrosodimethylamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:16 UTC

Update Date

2026-08-22 09:55:22 UTC

Accession Number

CHEM000177

Identification

Common Name

N-Nitrosodimethylamine

Class

Small Molecule

Description

N-Nitrosodimethylamine is found in pepper (Capsicum annuum). N-Nitrosodimethylamine is a food contaminant especially in cured meat products. N-Nitrosodimethylamine (NDMA), also known as dimethylnitrosamine (DMN), is a semi-volatile organic chemical that is highly toxic and is a suspected human carcinogen. The US Environmental Protection Agency has determined that the maximum admissible concentration of NDMA in drinking water is 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 is an industrial by-product or waste product of several industrial processes. It first came to attention as a groundwater contaminant in California in 1998 and 1999 at several sites that produced rocket fuel. Manufacturing of unsymmetrical dimethylhydrazine (UDMH), which is a component of rocket fuel that requires NDMA for its synthesis, proved to be the culprit in these cases. 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 belongs to the family of Nitrosamines. These are compounds containing the nitrosamine functional group, with the structure R2NNO.

Contaminant Sources

Clean Air Act Chemicals
Disinfection Byproducts
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2A
My Exposome Chemicals
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Cigarette Toxin
Food Toxin
Household Toxin
Industrial By-product/Pollutant
Industrial/Workplace Toxin
Metabolite
Nitrite
Organic Compound
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1,1-Dimethyl-2-oxohydrazine	ChEBI
Dimethylnitrosamine	ChEBI
Dimethylnitrosoamine	ChEBI
DMN	ChEBI
N,N-Dimethylnitrosamine	ChEBI
N Nitrosodimethylamine	MeSH
Nitrosodimethylamine, ndma	MeSH
Nitrosodimethylamine	MeSH
NDMA nitrosodimethylamine	MeSH
(CH3)2NNO	HMDB
Dimethyl-nitrosamine	HMDB
Dimethylnitrosamin	HMDB
DMNA	HMDB
N, N-Dimethylnitrosamine	HMDB
N-Dimethyl-nitrosamine	HMDB
N-Dimethylnitrosoamine	HMDB
N-Methyl-N-nitroso-methamine	HMDB
N-Methyl-N-nitroso-methanamine	HMDB
N-Methyl-N-nitrosomethanamine	HMDB
N-Methyl-N-nitrosomethanamine, 9ci	HMDB
N-Nitroaodimethylamine	HMDB
N-nitroso-Dimethylamine	HMDB
N-nitroso-N,N-Dimethylamine	HMDB
NDMA	HMDB
Nitrous dimethylamide	HMDB

Chemical Formula

C₂H₆N₂O

Average Molecular Mass

74.082 g/mol

Monoisotopic Mass

74.048 g/mol

CAS Registry Number

62-75-9

IUPAC Name

N,N-dimethylnitrous amide

Traditional Name

nitrosodimethylamine

SMILES

CN(C)N=O

InChI Identifier

InChI=1S/C2H6N2O/c1-4(2)3-5/h1-2H3

InChI Key

UMFJAHHVKNCGLG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organic n-nitroso compounds. These are organic compounds containing a n-nitroso group -NN=O.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Organic nitroso compounds

Direct Parent

Organic N-nitroso compounds

Alternative Parents

Substituents

Organic n-nitroso compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

nitrosamine (CHEBI:35807 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

mutagen

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Yellow liquid. (6)

Experimental Properties

Property	Value
Melting Point	< 25°C
Boiling Point	154 °C
Solubility	1000 mg/mL at 24°C

Predicted Properties

Property	Value	Source
Water Solubility	106 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	0.039	ChemAxon
logS	0.15	ALOGPS
pKa (Strongest Basic)	3.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	20.05 m³·mol⁻¹	ChemAxon
Polarizability	7.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-6d29f9f7a8384c52f7b5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-9000000000-2df59bc19d1d15592467	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-9000000000-744c0a10617e87137cd5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-9000000000-f3f3d5174fd1edee28a6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-9000000000-f3f3d5174fd1edee28a6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-9000000000-2df59bc19d1d15592467	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-9000000000-4d289a54c5a2591daa33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-004i-9000000000-5a8fb7bb4f334a3f8445	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-004i-9000000000-d0dbc7bf8508475d923d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-004i-9000000000-744c0a10617e87137cd5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-05b7b59e6e0b8b9fc245	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-3910f1d3f8050d839f82	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9000000000-4ab1e2e6522e0f1a2eb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-eea50ce8e07045a0ad14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-fed38e3c1ad8e9420fd6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-0d360c627861df90248b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-87753cf4baa848fb8803	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-87753cf4baa848fb8803	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9000000000-fa476a49943ea98d47ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-777dda7ebfc4febb2166	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-19ff9f5df3b310d929a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9000000000-876fe1a3967818d2717c	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dl-9000000000-25a83bcedddadb3e2b4e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (6) ; inhalation (6) ; dermal (6)

Mechanism of Toxicity

The mechanism of NDMAinduced liver toxicity is not clearly understood but may be related to alkylation of cellular protein. (6)

Metabolism

Evidence from in vitro and in vivo studies with rodents indicates that NDMA is metabolized by hydroxylation of the alpha-carbon, followed by formation of formaldehyde, molecular nitrogen and a methylating agent, which is considered to be the carcinogenic form. Recent evidence suggests that a significant proportion of NDMA is metabolized via a denitrosation mechanism. (6)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2A, probably carcinogenic to humans. (5)

Uses/Sources

The general population might be exposed to NDMA from a wide variety of sources, including environmental, consumer, and occupational sources. The primary sources of human exposure to NDMA are tobacco smoke, chewing tobacco, diet (cured meats [particularly bacon], beer, fish, cheese, and other food items), toiletry and cosmetic products (for example, shampoos and cleansers), interior air of cars, and various other household goods, such as detergents and pesticides. In addition, NDMA can form in the stomach during digestion of alkylamine-containing foods. Alkylamines are naturally occurring compounds which are found in some drugs and in a variety of foods. Infants may be exposed to NDMA from the use of rubber baby bottle nipples and pacifiers which may contain very small amounts of NDMA, from ingestion of contaminated infant formulas, and from breast milk of some nursing mothers. Very low levels of NDMA have been found in some samples of human breast milk. Occupational exposure may happen in a large number of places including industries such as tanneries, pesticide manufacturing plants, rubber and tire manufacturing plants, alkylamine manufacture/use industries, fish processing industries, foundries, and dye manufacturing plants. Researchers making or handling NDMA may also be exposed to this compound if it passes through the rubber gloves they wear during laboratory work. (6)

Minimum Risk Level

Not Available

Health Effects

NDMA is very harmful to the liver of animals and humans. Moreover, although there are no reports of NDMA causing cancer in humans, it is reasonable to expect that exposure to NDMA by eating, drinking, or breathing could also cause cancer in humans. (6)

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0031419

FooDB ID