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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:50:55 UTC

Update Date

2021-09-26 23:09:54 UTC

HMDB ID

HMDB0255256

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N,N-Dimethyl-4-nitrosoaniline

Description

N,N-dimethyl-4-nitrosoaniline, also known as 4-(dimethylamino)nitrosobenzene or 4-nitroso-N,N-dimethylaniline, belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. N,N-dimethyl-4-nitrosoaniline is a strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). N,n-dimethyl-4-nitrosoaniline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N,N-Dimethyl-4-nitrosoaniline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-(Dimethylamino)nitrosobenzene	ChEBI
4-Nitroso-N,N-dimethylaniline	ChEBI
4-Nitrosodimethylaniline	ChEBI
Dimethyl(p-nitrosophenyl)amine	ChEBI
Dimethyl-p-nitrosoaniline	ChEBI
N,N-Dimethyl-p-nitrosoaniline	ChEBI
NDMA	ChEBI
p-(Dimethylamino)nitrosobenzene	ChEBI
p-(N,N-Dimethylamino)nitrosobenzene	ChEBI
p-Nitroso dimethylaniline	ChEBI
p-Nitroso-N,N-dimethylaniline	ChEBI
p-Nitrosodimethylanilide	ChEBI
Paranitrosodimethylanilide	ChEBI
Accelerine	Kegg
4-Nitrosodimethylaniline monohydrochloride	MeSH
NDMA nitrosodimethylaniline	MeSH
p-Nitrosodimethylaniline	MeSH
Para-nitrosodimethylaniline	MeSH

Chemical Formula

C₈H₁₀N₂O

Average Molecular Weight

150.181

Monoisotopic Molecular Weight

150.07931295

IUPAC Name

N,N-dimethyl-4-nitrosoaniline

Traditional Name

NDMA

CAS Registry Number

Not Available

SMILES

CN(C)C1=CC=C(C=C1)N=O

InChI Identifier

InChI=1S/C8H10N2O/c1-10(2)8-5-3-7(9-11)4-6-8/h3-6H,1-2H3

InChI Key

CMEWLCATCRTSGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylarylamines

Alternative Parents

Substituents

Aniline or substituted anilines
Dialkylarylamine
Benzenoid
Monocyclic benzene moiety
Organic nitroso compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
C-nitroso compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

nitroso compound (CHEBI:59990 )
N,N-dimethylaniline (CHEBI:59990 )
a small molecule (CPD-12424 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.13	ALOGPS
logP	2.16	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	3.22	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	2	ChemAxon
Refractivity	46.06 m³·mol⁻¹	ChemAxon
Polarizability	15.93 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	134.402	30932474
DeepCCS	[M-H]-	130.919	30932474
DeepCCS	[M-2H]-	168.239	30932474
DeepCCS	[M+Na]+	143.51	30932474
AllCCS	[M+H]+	131.1	32859911
AllCCS	[M+H-H2O]+	126.6	32859911
AllCCS	[M+NH4]+	135.3	32859911
AllCCS	[M+Na]+	136.5	32859911
AllCCS	[M-H]-	130.8	32859911
AllCCS	[M+Na-2H]-	132.1	32859911
AllCCS	[M+HCOO]-	133.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N,N-Dimethyl-4-nitrosoaniline	CN(C)C1=CC=C(C=C1)N=O	2247.4	Standard polar	33892256
N,N-Dimethyl-4-nitrosoaniline	CN(C)C1=CC=C(C=C1)N=O	1599.7	Standard non polar	33892256
N,N-Dimethyl-4-nitrosoaniline	CN(C)C1=CC=C(C=C1)N=O	1589.4	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,N-Dimethyl-4-nitrosoaniline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fa7-9800000000-f6ded2fd87d999598e44	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N-Dimethyl-4-nitrosoaniline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 75V, Positive-QTOF	splash10-001i-1900000000-2126d7c4e492be5eafdb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 90V, Positive-QTOF	splash10-001i-3900000000-acd6730e117b5ed408d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 45V, Positive-QTOF	splash10-0udi-0900000000-02c48040e7eed6084266	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 60V, Positive-QTOF	splash10-0f89-0900000000-8d385c83e2ff5d360009	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 15V, Positive-QTOF	splash10-0udi-0900000000-4b10611eda4be928602f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 10V, Positive-QTOF	splash10-0udi-0900000000-3da1da2f8cd37abc6e70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 20V, Positive-QTOF	splash10-0udi-0900000000-0bce61bf0e2256438f34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 40V, Positive-QTOF	splash10-0zg0-2900000000-5513e2add4e5830adc79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 10V, Negative-QTOF	splash10-0002-0900000000-be44d1bbb49dc94eec31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 20V, Negative-QTOF	splash10-0002-0900000000-2728ccb1a117c4425677	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-Dimethyl-4-nitrosoaniline 40V, Negative-QTOF	splash10-0532-1900000000-c133bc97a60a7039b351	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C19680

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8749

PDB ID

Not Available

ChEBI ID

59990

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N,N-Dimethyl-4-nitrosoaniline (HMDB0255256)

MOL for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

3D MOL for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

3D SDF for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

3D-SDF for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

PDB for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

3D PDB for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

SMILES for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

INCHI for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

Structure for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

3D Structure for HMDB0255256 (N,N-Dimethyl-4-nitrosoaniline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra