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Showing Compound N-Nitrosodimethylamine (FDB003496)

Record Information
Version1.0
Creation date2010-04-08 22:05:49 UTC
Update date2020-02-24 19:10:45 UTC
Primary IDFDB003496
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Nitrosodimethylamine
DescriptionFood contaminant especies 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 is found in many foods, some of which are green bell pepper, yellow bell pepper, red bell pepper, and orange bell pepper.
CAS Number62-75-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
1,1-Dimethyl-2-oxohydrazineChEBI
DimethylnitrosamineChEBI
DimethylnitrosoamineChEBI
DMNChEBI
N,N-DimethylnitrosamineChEBI
N NitrosodimethylamineMeSH
Nitrosodimethylamine, ndmaMeSH
NitrosodimethylamineMeSH
NDMA nitrosodimethylamineMeSH
(CH3)2NNOHMDB
Dimethyl-nitrosamineHMDB
DimethylnitrosaminHMDB
DMNAHMDB
N, N-DimethylnitrosamineHMDB
N-Dimethyl-nitrosamineHMDB
N-DimethylnitrosoamineHMDB
N-Methyl-N-nitroso-methamineHMDB
N-Methyl-N-nitroso-methanamineHMDB
N-Methyl-N-nitrosomethanamineHMDB
N-Methyl-N-nitrosomethanamine, 9ciHMDB
N-NitroaodimethylamineHMDB
N-nitroso-DimethylamineHMDB
N-nitroso-N,N-DimethylamineHMDB
NDMAHMDB
Nitrous dimethylamideHMDB
Dimethylamine, n-nitroso-biospider
Dimethylnitrosamin (german)biospider
Methamine, n-methyl-n-nitroso-biospider
Methanamine, n-methyl-n-nitroso-biospider
N nitrosodimethylaminebiospider
N-dimethyl-nitrosaminebiospider
N-dimethylnitrosoaminebiospider
N-methyl-n-nitroso-methanaminebiospider
N-methyl-n-nitrosomethanaminebiospider
N-Methyl-N-nitrosomethanamine, 9CIdb_source
N-nitroaodimethylaminebiospider
N-Nitroso-dimethylamineHMDB
N-nitroso-n,n-dimethylaminebiospider
N, n-dimethylnitrosaminebiospider
N,n-dimethylnitrosaminebiospider
Ndma nitrosodimethylaminebiospider
Nitrosamine, dimethyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility106 g/LALOGPS
logP-0.53ALOGPS
logP0.039ChemAxon
logS0.15ALOGPS
pKa (Strongest Basic)3.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.05 m³·mol⁻¹ChemAxon
Polarizability7.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC2H6N2O
IUPAC namedimethyl(nitroso)amine
InChI IdentifierInChI=1S/C2H6N2O/c1-4(2)3-5/h1-2H3
InChI KeyUMFJAHHVKNCGLG-UHFFFAOYSA-N
Isomeric SMILESCN(C)N=O
Average Molecular Weight74.0818
Monoisotopic Molecular Weight74.048012824
Classification
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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic nitroso compounds
Direct ParentOrganic N-nitroso compounds
Alternative Parents
Substituents
  • Organic n-nitroso compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Industrial process:

Role

Indirect biological role:

Environmental role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 32.43%; H 8.16%; N 37.81%; O 21.60%DFC
Melting Point< 25 oC
Boiling PointBp774 153°DFC
Experimental Water Solubility1000 mg/mL at 24 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-0.57HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd104 1.01DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00dl-9000000000-25a83bcedddadb3e2b4e2014-09-20View Spectrum
Predicted GC-MSN-Nitrosodimethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-6d29f9f7a8384c52f7b5Spectrum
Predicted GC-MSN-Nitrosodimethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Nitrosodimethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9000000000-2df59bc19d1d155924672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9000000000-744c0a10617e87137cd52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9000000000-f3f3d5174fd1edee28a62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9000000000-f3f3d5174fd1edee28a62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9000000000-2df59bc19d1d155924672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9000000000-4d289a54c5a2591daa332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-004i-9000000000-5a8fb7bb4f334a3f84452021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-004i-9000000000-d0dbc7bf8508475d923d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-004i-9000000000-744c0a10617e87137cd52021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-05b7b59e6e0b8b9fc2452016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-3910f1d3f8050d839f822016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9000000000-4ab1e2e6522e0f1a2eb32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-eea50ce8e07045a0ad142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-fed38e3c1ad8e9420fd62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-0d360c627861df90248b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-87753cf4baa848fb88032021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-87753cf4baa848fb88032021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-fa476a49943ea98d47ff2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-777dda7ebfc4febb21662021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-19ff9f5df3b310d929a02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-876fe1a3967818d2717c2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
ChemSpider ID5894
ChEMBL IDCHEMBL117311
KEGG Compound IDC14704
Pubchem Compound ID6124
Pubchem Substance IDNot Available
ChEBI ID35807
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31419
CRC / DFC (Dictionary of Food Compounds) IDCZW84-U:CZW84-U
EAFUS IDNot Available
Dr. Duke IDN-NITROSO-DIMETHYLAMINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDN-Nitrosodimethylamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).