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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:01 UTC
Update Date2022-03-07 02:52:58 UTC
HMDB IDHMDB0031419
Secondary Accession Numbers
  • HMDB31419
Metabolite Identification
Common NameN-Nitrosodimethylamine
DescriptionN-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
Data?1563862123
Synonyms
ValueSource
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
Chemical FormulaC2H6N2O
Average Molecular Weight74.0818
Monoisotopic Molecular Weight74.048012824
IUPAC Namedimethyl(nitroso)amine
Traditional Namenitrosodimethylamine
CAS Registry Number62-75-9
SMILES
CN(C)N=O
InChI Identifier
InChI=1S/C2H6N2O/c1-4(2)3-5/h1-2H3
InChI KeyUMFJAHHVKNCGLG-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.
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 24 °CNot Available
LogP-0.57Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.38431661259
DarkChem[M-H]-105.39131661259
DeepCCS[M+H]+118.94230932474
DeepCCS[M-H]-117.04630932474
DeepCCS[M-2H]-152.40430932474
DeepCCS[M+Na]+126.81130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-NitrosodimethylamineCN(C)N=O1275.6Standard polar33892256
N-NitrosodimethylamineCN(C)N=O622.4Standard non polar33892256
N-NitrosodimethylamineCN(C)N=O745.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Nitrosodimethylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-6d29f9f7a8384c52f7b52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Nitrosodimethylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Nitrosodimethylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9000000000-25a83bcedddadb3e2b4e2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOFsplash10-004i-9000000000-2df59bc19d1d155924672017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOFsplash10-004i-9000000000-744c0a10617e87137cd52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOFsplash10-004i-9000000000-f3f3d5174fd1edee28a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOFsplash10-004i-9000000000-f3f3d5174fd1edee28a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOFsplash10-004i-9000000000-2df59bc19d1d155924672017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Nitrosodimethylamine LC-ESI-QFT , positive-QTOFsplash10-004i-9000000000-4d289a54c5a2591daa332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Nitrosodimethylamine 90V, Positive-QTOFsplash10-004i-9000000000-5a8fb7bb4f334a3f84452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Nitrosodimethylamine 45V, Positive-QTOFsplash10-004i-9000000000-d0dbc7bf8508475d923d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Nitrosodimethylamine 75V, Positive-QTOFsplash10-004i-9000000000-744c0a10617e87137cd52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 10V, Positive-QTOFsplash10-004i-9000000000-05b7b59e6e0b8b9fc2452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 20V, Positive-QTOFsplash10-004i-9000000000-3910f1d3f8050d839f822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 40V, Positive-QTOFsplash10-004l-9000000000-4ab1e2e6522e0f1a2eb32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 10V, Negative-QTOFsplash10-00di-9000000000-eea50ce8e07045a0ad142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 20V, Negative-QTOFsplash10-00di-9000000000-fed38e3c1ad8e9420fd62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 40V, Negative-QTOFsplash10-05fr-9000000000-0d360c627861df90248b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 10V, Negative-QTOFsplash10-00di-9000000000-87753cf4baa848fb88032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 20V, Negative-QTOFsplash10-00di-9000000000-87753cf4baa848fb88032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 40V, Negative-QTOFsplash10-05fu-9000000000-fa476a49943ea98d47ff2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 10V, Positive-QTOFsplash10-004i-9000000000-777dda7ebfc4febb21662021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 20V, Positive-QTOFsplash10-004i-9000000000-19ff9f5df3b310d929a02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosodimethylamine 40V, Positive-QTOFsplash10-002f-9000000000-876fe1a3967818d2717c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003496
KNApSAcK IDNot Available
Chemspider ID5894
KEGG Compound IDC14704
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Nitrosodimethylamine
METLIN IDNot Available
PubChem Compound6124
PDB IDNot Available
ChEBI ID35807
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1664021
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .