Livestock Metabolome Database: Showing metabocard for N-Nitrosodimethylamine (LMDB00674)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:55:11 UTC

Update Date

2016-09-23 18:45:41 UTC

Lmdb

LMDB00674

Secondary Accession Numbers

None

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 animal 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 animals 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 animal 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.

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 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

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Ruminal Fluid	Detected and Quantified	49.3 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	67.9 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	86.8 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	97 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	69.5 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	87.7 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	110.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	120.9 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	110 +/- 22 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	121 +/- 43 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	67 +/- 2 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	70 +/- 11 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	88 +/- 13 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	88 +/- 13 uM	Not Available	Bovine	Saleem F, Bouatra...	details