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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 18:42:42 UTC
Update Date2019-07-23 07:14:50 UTC
HMDB IDHMDB0060677
Secondary Accession Numbers
  • HMDB60677
Metabolite Identification
Common Name2,6-Dimethylaniline
Description2,6-Dimethylaniline, also known as 2,6-xylidine or 2,6-DMA, belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions. Treatment of AS52 cells with N-OH-2,6-dimethylaniline (2,6-DMA) and 2,6-DMAP led to intracellular production of reactive oxygen species (ROS). Comparative evaluation of the results indicates that the principal mechanism of mutagenic action is likely to be through redox cycling of intracellularly bound aminophenol/quinone imine structures to generate ROS rather than through formation of covalent DNA adducts. 2,6-Dimethylaniline is a strong basic compound (based on its pKa). In humans, 2,6-dimethylaniline is involved in lidocaine (local anaesthetic) metabolism pathway. 2,6-Dimethylaniline is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. These considerations do not rule out DNA adduct formation by monocyclic nitrenium ions because it has been established that the free nitrenium ion derived from 2,6-Dimethylaniline can form under aqueous conditions. DNA strand breaks were observed in a dose-dependent manner in AS52 cells when treated with each of the N-OH-2,6-Dimethylaniline and 2,6-DMAP.
Structure
Data?1563866090
Synonyms
ValueSource
1-Amino-2,6-dimethylbenzeneChEBI
2,6-DimethylbenzenamineChEBI
2,6-DimethylphenylamineChEBI
2,6-DMAChEBI
2,6-XylidineChEBI
2,6-XylylamineChEBI
2-Amino-1,3-dimethylbenzeneChEBI
2-Amino-1,3-xyleneChEBI
2-Amino-m-xyleneChEBI
O-XylidineChEBI
Vic-m-xylidineChEBI
2,6-Xylidine hydrochlorideHMDB
2,6-Xylidine, 3H-labeledHMDB
Chemical FormulaC8H11N
Average Molecular Weight121.1796
Monoisotopic Molecular Weight121.089149357
IUPAC Name2,6-dimethylaniline
Traditional Name2,6-dimethylaniline
CAS Registry NumberNot Available
SMILES
CC1=CC=CC(C)=C1N
InChI Identifier
InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3
InChI KeyUFFBMTHBGFGIHF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct Parentm-Xylenes
Alternative Parents
Substituents
  • M-xylene
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.12 g/LALOGPS
logP10(1.77) g/LALOGPS
logP10(2.17) g/LChemAxon
logS10(-1.4) g/LALOGPS
pKa (Strongest Basic)4.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.84 m³·mol⁻¹ChemAxon
Polarizability14.32 ųChemAxon
Number of Rings1ChemAxon
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]+125.73231661259
DarkChem[M-H]-121.63431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,6-DimethylanilineCC1=CC=CC(C)=C1N1915.7Standard polar33892256
2,6-DimethylanilineCC1=CC=CC(C)=C1N1135.0Standard non polar33892256
2,6-DimethylanilineCC1=CC=CC(C)=C1N1146.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,6-Dimethylaniline,1TMS,isomer #1CC1=CC=CC(C)=C1N[Si](C)(C)C1296.0Semi standard non polar33892256
2,6-Dimethylaniline,1TMS,isomer #1CC1=CC=CC(C)=C1N[Si](C)(C)C1266.4Standard non polar33892256
2,6-Dimethylaniline,1TMS,isomer #1CC1=CC=CC(C)=C1N[Si](C)(C)C1465.2Standard polar33892256
2,6-Dimethylaniline,2TMS,isomer #1CC1=CC=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C1358.1Semi standard non polar33892256
2,6-Dimethylaniline,2TMS,isomer #1CC1=CC=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C1444.7Standard non polar33892256
2,6-Dimethylaniline,2TMS,isomer #1CC1=CC=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C1484.2Standard polar33892256
2,6-Dimethylaniline,1TBDMS,isomer #1CC1=CC=CC(C)=C1N[Si](C)(C)C(C)(C)C1553.4Semi standard non polar33892256
2,6-Dimethylaniline,1TBDMS,isomer #1CC1=CC=CC(C)=C1N[Si](C)(C)C(C)(C)C1478.6Standard non polar33892256
2,6-Dimethylaniline,1TBDMS,isomer #1CC1=CC=CC(C)=C1N[Si](C)(C)C(C)(C)C1665.3Standard polar33892256
2,6-Dimethylaniline,2TBDMS,isomer #1CC1=CC=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1768.6Semi standard non polar33892256
2,6-Dimethylaniline,2TBDMS,isomer #1CC1=CC=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1853.9Standard non polar33892256
2,6-Dimethylaniline,2TBDMS,isomer #1CC1=CC=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1767.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized)splash10-05i0-8900000000-33c23e2a5227705d55442017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized)splash10-0kmi-9400000000-1d6fefd12c8955bae28e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized)splash10-00di-4900000000-adba26f261e79021dda82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline CI-B (Non-derivatized)splash10-00di-0900000000-60300dd43db5cd2a3ce82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized)splash10-00di-3900000000-4aea984cccfc0b0c54602017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized)splash10-05i0-8900000000-33c23e2a5227705d55442018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized)splash10-0kmi-9400000000-1d6fefd12c8955bae28e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized)splash10-00di-4900000000-adba26f261e79021dda82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline CI-B (Non-derivatized)splash10-00di-0900000000-60300dd43db5cd2a3ce82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized)splash10-00di-3900000000-4aea984cccfc0b0c54602018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6-Dimethylaniline GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3900000000-aaf33e5465b639ec8ce62017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6-Dimethylaniline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-05fr-4900000000-5a78022e1a4f7404ff742014-10-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-f0e30e85859e03c08f002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QTOF , positive-QTOFsplash10-0a6r-5900000000-a6314a94dc1796788f212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QTOF , positive-QTOFsplash10-0fb9-9000000000-87bb3c76b8e5f33dd07f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOFsplash10-00di-1900000000-b7f88fb029beffffe8ac2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOFsplash10-0ab9-1900000000-d65ee9324d0f1c4df6f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOFsplash10-0a6r-7900000000-2e6e430af0c7617827552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOFsplash10-004i-9200000000-b736963612d2417012032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOFsplash10-004i-9100000000-55b02455925ca45960a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-ITFT , positive-QTOFsplash10-05fr-0900000000-cf4cc10524595fe05f362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-ITFT , positive-QTOFsplash10-0a4i-1900000000-1242019b90e4219be0092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-ITFT , positive-QTOFsplash10-05fr-0900000000-f64a4a9c21cc92f7ac5f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0900000000-463463596d7c0b2ab2cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QFT , positive-QTOFsplash10-00di-0900000000-462e631b8e496a2f6da02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QFT , positive-QTOFsplash10-00di-0900000000-c1cbe274b163a350a4b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline 20V, Positive-QTOFsplash10-0a6r-5900000000-b40fcb93cfce6104aee82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline 10V, Positive-QTOFsplash10-00di-0900000000-b416dcd15fe4c9971d142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline 61V, Positive-QTOFsplash10-05fr-1900000000-909d1c88363b98e54b2d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline 40V, Positive-QTOFsplash10-0fb9-9000000000-a4fc73e1c85294a790be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Dimethylaniline 80V, Positive-QTOFsplash10-0a4i-1900000000-3c260372bd898314db9b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethylaniline 10V, Positive-QTOFsplash10-00di-0900000000-44543478974ee8f8609c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethylaniline 20V, Positive-QTOFsplash10-00di-1900000000-57461cdd2ba550b0d0272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethylaniline 40V, Positive-QTOFsplash10-0udm-9000000000-a273967b085862ad8dc02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethylaniline 10V, Negative-QTOFsplash10-00di-0900000000-07ac069740b06f649d102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethylaniline 20V, Negative-QTOFsplash10-00di-0900000000-07ac069740b06f649d102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethylaniline 40V, Negative-QTOFsplash10-00di-5900000000-8ce949a2c31ce45b62892016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11004
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,6-Xylidine
METLIN IDNot Available
PubChem Compound6896
PDB IDNot Available
ChEBI ID28738
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available