ContaminantDB: 2,6-Dimethylaniline

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:53:52 UTC

Update Date

2026-04-17 19:28:36 UTC

Accession Number

CHEM003178

Identification

Common Name

2,6-Dimethylaniline

Class

Small Molecule

Description

2,6-Dimethylaniline is a metabolite of lidocaine. Lidocaine, Xylocaine, or lignocaine is a common local anesthetic and antiarrhythmic drug. Lidocaine is used topically to relieve itching, burning and pain from skin inflammations, injected as a dental anesthetic or as a local anesthetic for minor surgery.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 2B
My Exposome Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Cigarette Toxin
Drug
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
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

Chemical Formula

C₈H₁₁N

Average Molecular Mass

121.180 g/mol

Monoisotopic Mass

121.089 g/mol

CAS Registry Number

87-62-7

IUPAC Name

2,6-dimethylaniline

Traditional Name

2,6-dimethylaniline

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 Key

UFFBMTHBGFGIHF-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

m-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

primary arylamine (CHEBI:28738 )
dimethylaniline (CHEBI:28738 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Kidney
Liver

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	11.45°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.12 g/L	ALOGPS
logP	1.77	ALOGPS
logP	2.17	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	4.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.84 m³·mol⁻¹	ChemAxon
Polarizability	14.32 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i0-8900000000-33c23e2a5227705d5544	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kmi-9400000000-1d6fefd12c8955bae28e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-4900000000-adba26f261e79021dda8	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-00di-0900000000-60300dd43db5cd2a3ce8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-3900000000-4aea984cccfc0b0c5460	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i0-8900000000-33c23e2a5227705d5544	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kmi-9400000000-1d6fefd12c8955bae28e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-4900000000-adba26f261e79021dda8	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-00di-0900000000-60300dd43db5cd2a3ce8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-3900000000-4aea984cccfc0b0c5460	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3900000000-aaf33e5465b639ec8ce6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-f0e30e85859e03c08f00	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a6r-5900000000-a6314a94dc1796788f21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0fb9-9000000000-87bb3c76b8e5f33dd07f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-1900000000-b7f88fb029beffffe8ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-1900000000-d65ee9324d0f1c4df6f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a6r-7900000000-2e6e430af0c761782755	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9200000000-b736963612d241701203	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9100000000-55b02455925ca45960a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05fr-0900000000-cf4cc10524595fe05f36	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-1900000000-1242019b90e4219be009	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05fr-0900000000-f64a4a9c21cc92f7ac5f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0900000000-463463596d7c0b2ab2cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0900000000-462e631b8e496a2f6da0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0900000000-c1cbe274b163a350a4b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-5900000000-b40fcb93cfce6104aee8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-b416dcd15fe4c9971d14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 61V, Positive	splash10-05fr-1900000000-909d1c88363b98e54b2d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9000000000-a4fc73e1c85294a790be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-0a4i-1900000000-3c260372bd898314db9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-44543478974ee8f8609c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-57461cdd2ba550b0d027	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udm-9000000000-a273967b085862ad8dc0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-07ac069740b06f649d10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-07ac069740b06f649d10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-5900000000-8ce949a2c31ce45b6289	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05fr-4900000000-5a78022e1a4f7404ff74	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

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). DNA strand breaks were observed in a dose-dependent manner in AS52 cells when treated with each of the N-OH-2,6-DMA and 2,6-DMAP. 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. 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-DMA can form under aqueous conditions. (2)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (3)

Uses/Sources

2,6-Dimethylaniline is found in cigarette smoke; it is a pharmacologically inactive metabolite of some drugs (e.g., the local anesthetic lidocaine) and pesticides (e.g., metalaxyl); and it is an impurity in technical grade metalaxyl. (1)

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0060677

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

2,6-Xylidine

Chemspider ID

Not Available

ChEBI ID

28738

PubChem Compound ID

6896

Kegg Compound ID

C11004

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11765029

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18490435

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8374321

2,6-Dimethylaniline (CHEM003178)

Structure for CHEM003178: 2,6-Dimethylaniline