Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-06-18 18:42:42 UTC |
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Update Date | 2023-02-21 17:30:09 UTC |
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HMDB ID | HMDB0060677 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2,6-Dimethylaniline |
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Description | 2,6-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. |
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Structure | InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3 |
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Synonyms | Value | Source |
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1-Amino-2,6-dimethylbenzene | ChEBI | 2,6-Dimethylbenzenamine | ChEBI | 2,6-Dimethylphenylamine | ChEBI | 2,6-DMA | ChEBI | 2,6-Xylidine | ChEBI | 2,6-Xylylamine | ChEBI | 2-Amino-1,3-dimethylbenzene | ChEBI | 2-Amino-1,3-xylene | ChEBI | 2-Amino-m-xylene | ChEBI | O-Xylidine | ChEBI | Vic-m-xylidine | ChEBI | 2,6-Xylidine hydrochloride | HMDB | 2,6-Xylidine, 3H-labeled | HMDB |
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Chemical Formula | C8H11N |
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Average Molecular Weight | 121.1796 |
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Monoisotopic Molecular Weight | 121.089149357 |
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IUPAC Name | 2,6-dimethylaniline |
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Traditional Name | 2,6-dimethylaniline |
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CAS Registry Number | Not Available |
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SMILES | CC1=CC=CC(C)=C1N |
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InChI Identifier | InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3 |
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InChI Key | UFFBMTHBGFGIHF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Xylenes |
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Direct Parent | m-Xylenes |
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Alternative Parents | |
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Substituents | - M-xylene
- Aniline or substituted anilines
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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2,6-Dimethylaniline,1TMS,isomer #1 | CC1=CC=CC(C)=C1N[Si](C)(C)C | 1296.0 | Semi standard non polar | 33892256 | 2,6-Dimethylaniline,1TMS,isomer #1 | CC1=CC=CC(C)=C1N[Si](C)(C)C | 1266.4 | Standard non polar | 33892256 | 2,6-Dimethylaniline,1TMS,isomer #1 | CC1=CC=CC(C)=C1N[Si](C)(C)C | 1465.2 | Standard polar | 33892256 | 2,6-Dimethylaniline,2TMS,isomer #1 | CC1=CC=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C | 1358.1 | Semi standard non polar | 33892256 | 2,6-Dimethylaniline,2TMS,isomer #1 | CC1=CC=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C | 1444.7 | Standard non polar | 33892256 | 2,6-Dimethylaniline,2TMS,isomer #1 | CC1=CC=CC(C)=C1N([Si](C)(C)C)[Si](C)(C)C | 1484.2 | Standard polar | 33892256 | 2,6-Dimethylaniline,1TBDMS,isomer #1 | CC1=CC=CC(C)=C1N[Si](C)(C)C(C)(C)C | 1553.4 | Semi standard non polar | 33892256 | 2,6-Dimethylaniline,1TBDMS,isomer #1 | CC1=CC=CC(C)=C1N[Si](C)(C)C(C)(C)C | 1478.6 | Standard non polar | 33892256 | 2,6-Dimethylaniline,1TBDMS,isomer #1 | CC1=CC=CC(C)=C1N[Si](C)(C)C(C)(C)C | 1665.3 | Standard polar | 33892256 | 2,6-Dimethylaniline,2TBDMS,isomer #1 | CC1=CC=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1768.6 | Semi standard non polar | 33892256 | 2,6-Dimethylaniline,2TBDMS,isomer #1 | CC1=CC=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1853.9 | Standard non polar | 33892256 | 2,6-Dimethylaniline,2TBDMS,isomer #1 | CC1=CC=CC(C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1767.2 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized) | splash10-05i0-8900000000-33c23e2a5227705d5544 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized) | splash10-0kmi-9400000000-1d6fefd12c8955bae28e | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized) | splash10-00di-4900000000-adba26f261e79021dda8 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline CI-B (Non-derivatized) | splash10-00di-0900000000-60300dd43db5cd2a3ce8 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized) | splash10-00di-3900000000-4aea984cccfc0b0c5460 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized) | splash10-05i0-8900000000-33c23e2a5227705d5544 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized) | splash10-0kmi-9400000000-1d6fefd12c8955bae28e | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized) | splash10-00di-4900000000-adba26f261e79021dda8 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline CI-B (Non-derivatized) | splash10-00di-0900000000-60300dd43db5cd2a3ce8 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2,6-Dimethylaniline EI-B (Non-derivatized) | splash10-00di-3900000000-4aea984cccfc0b0c5460 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2,6-Dimethylaniline GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-3900000000-aaf33e5465b639ec8ce6 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2,6-Dimethylaniline GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-05fr-4900000000-5a78022e1a4f7404ff74 | 2014-10-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QTOF , positive-QTOF | splash10-00di-0900000000-f0e30e85859e03c08f00 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QTOF , positive-QTOF | splash10-0a6r-5900000000-a6314a94dc1796788f21 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QTOF , positive-QTOF | splash10-0fb9-9000000000-87bb3c76b8e5f33dd07f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOF | splash10-00di-1900000000-b7f88fb029beffffe8ac | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOF | splash10-0ab9-1900000000-d65ee9324d0f1c4df6f7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOF | splash10-0a6r-7900000000-2e6e430af0c761782755 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOF | splash10-004i-9200000000-b736963612d241701203 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QQ , positive-QTOF | splash10-004i-9100000000-55b02455925ca45960a0 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-ITFT , positive-QTOF | splash10-05fr-0900000000-cf4cc10524595fe05f36 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-ITFT , positive-QTOF | splash10-0a4i-1900000000-1242019b90e4219be009 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-ITFT , positive-QTOF | splash10-05fr-0900000000-f64a4a9c21cc92f7ac5f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-ITFT , positive-QTOF | splash10-0a4i-0900000000-463463596d7c0b2ab2cd | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QFT , positive-QTOF | splash10-00di-0900000000-462e631b8e496a2f6da0 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline LC-ESI-QFT , positive-QTOF | splash10-00di-0900000000-c1cbe274b163a350a4b9 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 20V, Positive-QTOF | splash10-0a6r-5900000000-b40fcb93cfce6104aee8 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 10V, Positive-QTOF | splash10-00di-0900000000-b416dcd15fe4c9971d14 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 61V, Positive-QTOF | splash10-05fr-1900000000-909d1c88363b98e54b2d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 40V, Positive-QTOF | splash10-0fb9-9000000000-a4fc73e1c85294a790be | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 80V, Positive-QTOF | splash10-0a4i-1900000000-3c260372bd898314db9b | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 55V, Positive-QTOF | splash10-05fr-0900000000-890715c9999018f1970b | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 35V, Positive-QTOF | splash10-00di-0900000000-89d9cf3d648456f74330 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 35V, Positive-QTOF | splash10-00di-0900000000-4635a67850ba5efe439a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 35V, Positive-QTOF | splash10-05fr-0900000000-2364daa3c2217abe43ed | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2,6-Dimethylaniline 55V, Positive-QTOF | splash10-0a4i-0900000000-a8eb4aae6d7c55d110e0 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,6-Dimethylaniline 10V, Negative-QTOF | splash10-00di-0900000000-07ac069740b06f649d10 | 2016-08-03 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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