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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:01 UTC

Update Date

2023-02-21 17:20:31 UTC

HMDB ID

HMDB0031419

Secondary Accession Numbers

HMDB31419

Metabolite Identification

Common Name

N-Nitrosodimethylamine

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

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 Weight

74.0818

Monoisotopic Molecular Weight

74.048012824

IUPAC Name

dimethyl(nitroso)amine

Traditional Name

nitrosodimethylamine

CAS Registry Number

62-75-9

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031419)
Cytoplasm (HMDB: HMDB0031419)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031419)

Parenteral

Inhalation (HMDB: HMDB0031419)
Dermal (HMDB: HMDB0031419)

Source

Endogenous

Endogenous (HMDB: HMDB0031419)

Plant

Plant (HMDB: HMDB0031419)

Exogenous

Food

Food (HMDB: HMDB0031419)

Vegetable

Fruit vegetable

Synthetic

Synthetic (HMDB: HMDB0031419)

Environmental

Wastewater (HMDB: HMDB0031419)
Tobacco Smoke (HMDB: HMDB0031419)

Process

Industrial process

Disinfection

Water Disinfection (HMDB: HMDB0031419)

Role

Environmental role

Air pollutant (HMDB: HMDB0031419)

Biological role

Mutagen (HMDB: HMDB0031419)
Mutagen (HMDB: HMDB0031419)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL at 24 °C	Not Available
LogP	-0.57	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	112.384	31661259
DarkChem	[M-H]-	105.391	31661259
DeepCCS	[M+H]+	118.942	30932474
DeepCCS	[M-H]-	117.046	30932474
DeepCCS	[M-2H]-	152.404	30932474
DeepCCS	[M+Na]+	126.811	30932474
AllCCS	[M+H]+	124.4	32859911
AllCCS	[M+H-H2O]+	120.0	32859911
AllCCS	[M+NH4]+	128.4	32859911
AllCCS	[M+Na]+	129.6	32859911
AllCCS	[M-H]-	129.7	32859911
AllCCS	[M+Na-2H]-	135.5	32859911
AllCCS	[M+HCOO]-	141.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Nitrosodimethylamine	CN(C)N=O	1275.6	Standard polar	33892256
N-Nitrosodimethylamine	CN(C)N=O	622.4	Standard non polar	33892256
N-Nitrosodimethylamine	CN(C)N=O	745.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitrosodimethylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-6d29f9f7a8384c52f7b5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitrosodimethylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitrosodimethylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dl-9000000000-25a83bcedddadb3e2b4e	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOF	splash10-004i-9000000000-2df59bc19d1d15592467	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOF	splash10-004i-9000000000-744c0a10617e87137cd5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOF	splash10-004i-9000000000-f3f3d5174fd1edee28a6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOF	splash10-004i-9000000000-f3f3d5174fd1edee28a6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOF	splash10-004i-9000000000-2df59bc19d1d15592467	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOF	splash10-004i-9000000000-4d289a54c5a2591daa33	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodimethylamine 90V, Positive-QTOF	splash10-004i-9000000000-5a8fb7bb4f334a3f8445	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodimethylamine 45V, Positive-QTOF	splash10-004i-9000000000-d0dbc7bf8508475d923d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Nitrosodimethylamine 75V, Positive-QTOF	splash10-004i-9000000000-744c0a10617e87137cd5	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 10V, Positive-QTOF	splash10-004i-9000000000-05b7b59e6e0b8b9fc245	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 20V, Positive-QTOF	splash10-004i-9000000000-3910f1d3f8050d839f82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 40V, Positive-QTOF	splash10-004l-9000000000-4ab1e2e6522e0f1a2eb3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 10V, Negative-QTOF	splash10-00di-9000000000-eea50ce8e07045a0ad14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 20V, Negative-QTOF	splash10-00di-9000000000-fed38e3c1ad8e9420fd6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 40V, Negative-QTOF	splash10-05fr-9000000000-0d360c627861df90248b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 10V, Negative-QTOF	splash10-00di-9000000000-87753cf4baa848fb8803	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 20V, Negative-QTOF	splash10-00di-9000000000-87753cf4baa848fb8803	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 40V, Negative-QTOF	splash10-05fu-9000000000-fa476a49943ea98d47ff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 10V, Positive-QTOF	splash10-004i-9000000000-777dda7ebfc4febb2166	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 20V, Positive-QTOF	splash10-004i-9000000000-19ff9f5df3b310d929a0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 40V, Positive-QTOF	splash10-002f-9000000000-876fe1a3967818d2717c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003496

KNApSAcK ID

Not Available

Chemspider ID

5894

KEGG Compound ID

C14704

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Nitrosodimethylamine

METLIN ID

Not Available

PubChem Compound

6124

PDB ID

Not Available

ChEBI ID

35807

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1664021

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Godoy W, Albano RM, Moraes EG, Pinho PR, Nunes RA, Saito EH, Higa C, Filho IM, Kruel CD, Schirmer CC, Gurski R, Lang MA, Pinto LF: CYP2A6/2A7 and CYP2E1 expression in human oesophageal mucosa: regional and inter-individual variation in expression and relevance to nitrosamine metabolism. Carcinogenesis. 2002 Apr;23(4):611-6. [PubMed:11960914 ]
Lee MF, Liu ML, Cheng AC, Tsai ML, Ho CT, Liou WS, Pan MH: Pterostilbene inhibits dimethylnitrosamine-induced liver fibrosis in rats. Food Chem. 2013 Jun 1;138(2-3):802-7. doi: 10.1016/j.foodchem.2012.11.094. Epub 2012 Dec 1. [PubMed:23411180 ]
Lee MF, Tsai ML, Sun PP, Chien LL, Cheng AC, Ma NJ, Ho CT, Pan MH: Phyto-power dietary supplement potently inhibits dimethylnitrosamine-induced liver fibrosis in rats. Food Funct. 2013 Feb 26;4(3):470-5. doi: 10.1039/c2fo30306j. [PubMed:23291610 ]
Kao HW, Chen CL, Chang WY, Chen JT, Lin WJ, Liu RS, Wang HE: (18)F-FBHGal for asialoglycoprotein receptor imaging in a hepatic fibrosis mouse model. Bioorg Med Chem. 2013 Feb 15;21(4):912-21. doi: 10.1016/j.bmc.2012.12.022. Epub 2012 Dec 22. [PubMed:23321012 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for N-Nitrosodimethylamine (HMDB0031419)

MOL for HMDB0031419 (N-Nitrosodimethylamine)

3D MOL for HMDB0031419 (N-Nitrosodimethylamine)

3D SDF for HMDB0031419 (N-Nitrosodimethylamine)

3D-SDF for HMDB0031419 (N-Nitrosodimethylamine)

PDB for HMDB0031419 (N-Nitrosodimethylamine)

3D PDB for HMDB0031419 (N-Nitrosodimethylamine)

SMILES for HMDB0031419 (N-Nitrosodimethylamine)

INCHI for HMDB0031419 (N-Nitrosodimethylamine)

Structure for HMDB0031419 (N-Nitrosodimethylamine)

3D Structure for HMDB0031419 (N-Nitrosodimethylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra