U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C8H11N
Molecular Weight 121.1796
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2,6-XYLIDINE

SMILES

CC1=CC=CC(C)=C1N

InChI

InChIKey=UFFBMTHBGFGIHF-UHFFFAOYSA-N
InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C8H11N
Molecular Weight 121.1796
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Transformation of BALB/c-3T3 cells: IV. Rank-ordered potency of 24 chemical responses detected in a sensitive new assay procedure.
1993 Jul
An update of the National Toxicology Program database on nasal carcinogens.
1997 Oct 31
Involvement of liver carboxylesterases in the in vitro metabolism of lidocaine.
2002 Jun
The effect of deuterium and fluorine substitution upon the mutagenicity of N-hydroxy-2,6-dimethylaniline.
2002 Sep 30
Determination of 2,6-dimethylaniline and o-toluidine impurities in preparations for local anaesthesia by the HPLC method with amperometric detection.
2002 Sep-Oct
Identification of DNA adducts using HPLC/MS/MS following in vitro and in vivo experiments with arylamines and nitroarenes.
2003 Oct
Pharmacokinetics of xylazine, 2,6-dimethylaniline, and tolazoline in tissues from yearling cattle and milk from mature dairy cows after sedation with xylazine hydrochloride and reversal with tolazoline hydrochloride.
2003 Summer
Update on olfactory mucosal metabolic enzymes: age-related changes and N-acetyltransferase activities.
2004
Determination of xylazine and its metabolites by GC-MS in equine urine for doping analysis.
2004 Apr 1
Liquid phase overtone spectral investigations of 2,6-dimethylaniline and 2,4-dimethylaniline-evidence for steric nature of the ortho effect and the consequent base weakening.
2004 Aug
Synthesis, structure and pharmacology of acyl-2,6-xylidines.
2004 May-Jun
Metabolic activation of 2,6-xylidine in the nasal olfactory mucosa and the mucosa of the upper alimentary and respiratory tracts in rats.
2004 Oct
Alkylaniline-hemoglobin adducts and risk of non-smoking-related bladder cancer.
2004 Oct 6
Determination of local anaesthetics and their impurities in pharmaceutical preparations using HPLC method with amperometric detection.
2005 Apr 29
A kinetically controlled trans bifunctionalized organoimido derivative of the Lindqvist-type hexamolybdate: synthesis, spectroscopic characterization, and crystal structure of (n-Bu4N)2{trans-[Mo6O17(NAr)2]} (Ar = 2,6-dimethylphenyl).
2005 Dec 26
Primary amido substituted diborane4 compounds and imidodiborate4 anions.
2005 Oct 7
DNA adduct formation by 2,6-dimethyl-, 3,5-dimethyl-, and 3-ethylaniline in vivo in mice.
2006 Aug
Production and characterization of laccase from Cyathus bulleri and its use in decolourization of recalcitrant textile dyes.
2006 Aug
Amine mediated proton transfer reaction and C-Cl bond activation of solvent chloroform by a trinuclear copper(II) complex of a glucopyranosylamine derived ligand.
2006 Aug 21
Changes in production of lignin degrading enzymes during interactions between mycelia of the tropical decomposer basidiomycetes Marasmiellus troyanus and Marasmius pallescens.
2006 Feb
Regioselective copper-catalyzed amination of chlorobenzoic acids: synthesis and solid-state structures of N-aryl anthranilic acid derivatives.
2006 Jan 6
Synthesis, structure, and characterization of molybdenum(VI) imido complexes with N-salicylidene-2-aminophenol.
2006 Jul 10
Pi-Pi complexation of bupivacaine and analogues with aromatic receptors: implications for overdose remediation.
2007
Similarities and differences between azomethines and ketimines: synthesis, materials characterization and structure of novel imines compounds.
2007 Apr
Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr.HCl, IMes.HCl and IXy.HCl.
2007 Aug 28
N-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-ylcarbon-yl)-N'-(2,6-dimethyl-phen-yl)thio-urea.
2007 Dec 6
Liquid-phase microextraction-gas chromatography-mass spectrometry for the determination of bromate, iodate, bromide and iodide in high-chloride matrix.
2007 May 4
Temperature investigations of E/Z isomers in ketimines based of p-dibenzoylobenzene with aniline and 2,6-dimethylaniline by infrared spectroscopy.
2007 Oct
Assessment of the medicines lidocaine, prilocaine, and their metabolites, 2,6-dimethylaniline and 2-methylaniline, for DNA adduct formation in rat tissues.
2008 Aug
N-(2,6-Dimethyl-phen-yl)benzene-sulfonamide.
2008 Aug 6
The importance of CH/pi hydrogen bonds in rational drug design: An ab initio fragment molecular orbital study to leukocyte-specific protein tyrosine (LCK) kinase.
2008 Dec 15
Quantitative mass spectrometric analysis of ropivacaine and bupivacaine in authentic, pharmaceutical and spiked human plasma without chromatographic separation.
2008 May 28
2,6-Dimethyl-anilinium chloride monohydrate.
2008 Nov 29
Kinetics and mechanism of 2,6-dimethyl-aniline degradation by hydroxyl radicals.
2009 Dec 30
N-(2,6-Dimethyl-phen-yl)succinamic acid.
2009 Feb 6
Kinetics of 2,6-dimethylaniline degradation by electro-Fenton process.
2009 Jan 30
Mixed carbene-isocyanide Pd(II) complexes: synthesis, structures and reactivity towards nucleophiles.
2009 Mar 28
Chemical oxidation of 2,6-dimethylaniline in the fenton process.
2009 Nov 15
N-(2,6-Dimethyl-phen-yl)-2-(2-thien-yl)acetamide.
2009 Nov 25
N-(2,6-Dimethyl-phen-yl)maleamic acid.
2009 Oct 23
Iron-catalyzed dehydrogenative phosphonation of N,N-dimethylanilines.
2009 Oct 28
Separation and analysis of dimethylaniline isomers by supercritical fluid chromatography--electrospray ionization tandem mass spectrometry.
2009 Oct 9
Drug impurity profiling by capillary electrophoresis/mass spectrometry using various ionization techniques.
2009 Sep
Chemical oxidation of 2,6-dimethylaniline by electrochemically generated Fenton's reagent.
2010 Apr 15
N-(2,6-Dimethyl-phen-yl)-4-methyl-benzene-sulfonamide.
2010 Apr 24
Monocyclic aromatic amines as potential human carcinogens: old is new again.
2010 Jan
N-(2,6-Dimethyl-phen-yl)succinimide.
2010 Jan 9
Third-order nonlinear optical properties and structures of (E)-N-(4-nitrobenzylidene)-2,6-dimethylaniline and (E)-N-(4-nitrobenzylidene)-2,3-dimethylaniline.
2010 May
Investigating the mechanisms of aromatic amine-induced protein free radical formation by quantitative structure-activity relationships: implications for drug-induced agranulocytosis.
2010 May 17
HPLC-DAD stability indicating determination of nitrofurazone and lidocaine hydrochloride in their combined topical dosage form.
2010 Sep
Patents
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:31:18 UTC 2023
Edited
by admin
on Thu Jul 06 00:31:18 UTC 2023
Record UNII
4FT62OX08D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2,6-XYLIDINE
HSDB  
Systematic Name English
2,6-DIMETHYLANILINE [USP IMPURITY]
Common Name English
2,6-DIMETHYLBENZENAMINE
Systematic Name English
BUPIVACAINE HYDROCHLORIDE IMPURITY F [EP IMPURITY]
Common Name English
XYLAZINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
XYLIDENE, 2,6-
Common Name English
2,6-DIMETHYLANILINE
Systematic Name English
MEPIVACAINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
XYLIDINE 2,6-DIMETHYLBENZENAMINE
MI  
Systematic Name English
2,6-DIMETHYLANILINE [IARC]
Common Name English
NCI-C56188
Code English
LIDOCAINE IMPURITY A [EP IMPURITY]
Common Name English
NSC-7098
Code English
O-XYLIDINE
Common Name English
ROPIVACAINE HYDROCHLORIDE MONOHYDRATE IMPURITY H [EP IMPURITY]
Common Name English
2,6-XYLIDINE [HSDB]
Common Name English
ROPIVACAINE RELATED COMPOUND A FREE BASE
Common Name English
LIDOCAINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
XYLIDINE 2,6-DIMETHYLBENZENAMINE [MI]
Common Name English
2-AMINO-1,3-XYLENE
Systematic Name English
BENZENAMINE, 2,6-DIMETHYL-
Systematic Name English
LIDOCAINE RELATED COMPOUND 2,6-DIMETHYLANILINE [USP IMPURITY]
Common Name English
1-AMINO-2,6-DIMETHYLBENZENE
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 90502
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
Code System Code Type Description
WIKIPEDIA
2,6-XYLIDINE
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID8026307
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
FDA UNII
4FT62OX08D
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
CAS
87-62-7
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
CHEBI
28738
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
MESH
C007766
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
MERCK INDEX
M11552
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY Merck Index
NSC
7098
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
PUBCHEM
6896
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-758-7
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
HSDB
2094
Created by admin on Thu Jul 06 00:31:19 UTC 2023 , Edited by admin on Thu Jul 06 00:31:19 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE INACTIVE
has unknown pharmacologic activity but is carcinogenic in rats (http://srsid.fda.gov:9618/ePS/SubstanceRelationship.do?substanceMode=update&calledFrom=viewUpdateIngredient&RELATIONSHIP_ID=128538&SUBSTANCE_ID=1422&BDNUM=0021807AA).
PLASMA
PARENT -> METABOLITE
IN VITRO
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
color comparison
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP