<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4272</id>
  <title>T3D4218</title>
  <common-name>2,6-Dimethylaniline</common-name>
  <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. </description>
  <cas>87-62-7</cas>
  <pubchem-id>6896</pubchem-id>
  <chemical-formula>C8H11N</chemical-formula>
  <weight>121.18</weight>
  <appearance></appearance>
  <melting-point>11.45°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure></route-of-exposure>
  <target nil="true"/>
  <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. (A15447)</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>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. (A15345)</use-source>
  <min-risk-level></min-risk-level>
  <health-effects></health-effects>
  <symptoms></symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2014-08-29T05:53:52Z</created-at>
  <updated-at type="dateTime">2026-04-17T19:28:36Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia></wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C11004</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>28738</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id></stitch-id>
  <drugbank-id></drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC1=CC=CC(C)=C1N</moldb-smiles>
  <moldb-formula>C8H11N</moldb-formula>
  <moldb-inchi>InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3</moldb-inchi>
  <moldb-inchikey>UFFBMTHBGFGIHF-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">121.1796</moldb-average-mass>
  <moldb-mono-mass type="decimal">121.089149357</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp></logp>
  <hmdb-id>HMDB60677</hmdb-id>
  <chembl-id>CHEMBL1340793</chembl-id>
  <chemspider-id>6630</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003178</chemdb-id>
  <dsstox-id>DTXSID8026307</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00008896</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>26.02</moldb-polar-surface-area>
  <moldb-refractivity>40.8408</moldb-refractivity>
  <moldb-polarizability>14.324038130244016</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>1</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>4.310516263500829</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>1</moldb-number-of-rings>
  <moldb-alogps-logp>1.77</moldb-alogps-logp>
  <moldb-alogps-logs>-1.37</moldb-alogps-logs>
  <moldb-alogps-solubility>5.12e+00 g/l</moldb-alogps-solubility>
</compound>
