2,6-Dimethylaniline (CHEM003178)

Record Information
Version1.0
Creation Date2014-08-29 05:53:52 UTC
Update Date2026-08-24 12:08:02 UTC
Accession NumberCHEM003178
Identification
Common Name2,6-Dimethylaniline
ClassSmall 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
  • PMT
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
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 Mass121.180 g/mol
Monoisotopic Mass121.089 g/mol
CAS Registry Number87-62-7
IUPAC Name2,6-dimethylaniline
Traditional Name2,6-dimethylaniline
SMILESCC1=CC=CC(C)=C1N
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point11.45°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.12 g/LALOGPS
logP1.77ALOGPS
logP2.17ChemAxon
logS-1.4ALOGPS
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
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityTreatment 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)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (3)
Uses/Sources2,6-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 LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0060677
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link2,6-Xylidine
Chemspider IDNot Available
ChEBI ID28738
PubChem Compound ID6896
Kegg Compound IDC11004
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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