EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

2,6-xylidine
benzenamine, 2,6-dimethyl-

Supplier Sponsors

Name:2,6-dimethylaniline
CAS Number: 87-62-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-758-7
FDA UNII: 4FT62OX08D
Nikkaji Web:J43.456F
Beilstein Number:0636332
MDL:MFCD00007747
XlogP3:1.80 (est)
Molecular Weight:121.18267000
Formula:C8 H11 N
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.98400 @ 25.00 °C.
Melting Point: 11.20 °C. @ 760.00 mm Hg
Boiling Point: 215.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.130000 mmHg @ 25.00 °C. (est)
Flash Point: 196.00 °F. TCC ( 91.11 °C. )
logP (o/w): 1.840
Soluble in:
 water, 2666 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BASF
2,4-Xylidine
Santa Cruz Biotechnology
For experimental / research use only.
2,6-Dimethylaniline ≥95%
Sigma-Aldrich: Aldrich
For experimental / research use only.
2,6-Dimethylaniline 99%
TCI AMERICA
For experimental / research use only.
2,6-Dimethylaniline >99.0%(GC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 707 mg/kg
National Technical Information Service. Vol. PB214-270

oral-rat LD50 840 mg/kg
BLOOD: CHANGES IN SPLEEN BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Toxicology and Applied Pharmacology. Vol. 22, Pg. 153, 1972.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for 2,6-xylidine usage levels up to:
 not for fragrance use.
 
Recommendation for 2,6-xylidine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
NIOSH International Chemical Safety Cards:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA Substance Registry Services (TSCA):87-62-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6896
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2,6-dimethylaniline
Chemidplus:0000087627
EPA/NOAA CAMEO:hazardous materials
RTECS:87-62-7
 
References:
 2,6-dimethylaniline
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:87-62-7
Pubchem (cid):6896
Pubchem (sid):134971709
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C11004
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2921.49.5000
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
2-amino-1,3-dimethylbenzene
2-amino-1,3-xylene
1-amino-2,6-dimethylbenzene
2-amino-m-xylene
 aniline, 2,6-dimethyl-
 benzenamine, 2,6-dimethyl-
 benzene, 2-amino-1,3-dimethyl-
2,6-dimethyl aniline
2,6-dimethylanilin
2,6-dimethylaniline
2,6-dimethylphenylamine
o-xylidine
2,6-xylylamine
 

Articles:

PubMed:Formation of N-nitrosamines by chloramination or ozonation of amines listed in Pollutant Release and Transfer Registers (PRTRs).
PubMed:Determination of xylazine and 2,6-xylidine in animal tissues by liquid chromatography-tandem mass spectrometry.
PubMed:Elevated 4-aminobiphenyl and 2,6-dimethylaniline hemoglobin adducts and increased risk of bladder cancer among lifelong nonsmokers--The Shanghai Bladder Cancer Study.
PubMed:Prilocaine- and lidocaine-induced methemoglobinemia is caused by human carboxylesterase-, CYP2E1-, and CYP3A4-mediated metabolic activation.
PubMed:Genotoxicity of 2,6- and 3,5-dimethylaniline in cultured mammalian cells: the role of reactive oxygen species.
PubMed:Effect of carrier composition on 2,6-dimethylaniline degradation in aqueous solution by fluidized-bed Fenton process.
PubMed:Further investigations into the genotoxicity of 2,6-xylidine and one of its key metabolites.
PubMed:Occurrence and removal of lidocaine, tramadol, venlafaxine, and their metabolites in German wastewater treatment plants.
PubMed:Oxidation of 2,6-dimethylaniline by the Fenton, electro-Fenton and photoelectro-Fenton processes.
PubMed:Kinetics of 2,6-dimethylaniline oxidation by various Fenton processes.
PubMed:Third-order nonlinear optical properties and structures of (E)-N-(4-nitrobenzylidene)-2,6-dimethylaniline and (E)-N-(4-nitrobenzylidene)-2,3-dimethylaniline.
PubMed:Chemical oxidation of 2,6-dimethylaniline in the fenton process.
PubMed:Chemical oxidation of 2,6-dimethylaniline by electrochemically generated Fenton's reagent.
PubMed:Iron-catalyzed dehydrogenative phosphonation of N,N-dimethylanilines.
PubMed:Separation and analysis of dimethylaniline isomers by supercritical fluid chromatography--electrospray ionization tandem mass spectrometry.
PubMed:Kinetics and mechanism of 2,6-dimethyl-aniline degradation by hydroxyl radicals.
PubMed:Retention time prediction of compounds in Grob standard mixture for apolar capillary columns in temperature-programmed gas chromatography.
PubMed:Kinetics of 2,6-dimethylaniline degradation by electro-Fenton process.
PubMed:Assessment of the medicines lidocaine, prilocaine, and their metabolites, 2,6-dimethylaniline and 2-methylaniline, for DNA adduct formation in rat tissues.
PubMed:Temperature investigations of E/Z isomers in ketimines based of p-dibenzoylobenzene with aniline and 2,6-dimethylaniline by infrared spectroscopy.
PubMed:DNA adduct formation by 2,6-dimethyl-, 3,5-dimethyl-, and 3-ethylaniline in vivo in mice.
PubMed:Amine mediated proton transfer reaction and C-Cl bond activation of solvent chloroform by a trinuclear copper(II) complex of a glucopyranosylamine derived ligand.
PubMed:Changes in production of lignin degrading enzymes during interactions between mycelia of the tropical decomposer basidiomycetes Marasmiellus troyanus and Marasmius pallescens.
PubMed:Mechanisms of cytotoxicity of selected organogold(III) compounds.
PubMed:Solution chemistry and cytotoxic properties of novel organogold(III) compounds.
PubMed:Synthesis, structure and pharmacology of acyl-2,6-xylidines.
PubMed:Gold complexes inhibit mitochondrial thioredoxin reductase: consequences on mitochondrial functions.
PubMed:Metabolic activation of 2,6-xylidine in the nasal olfactory mucosa and the mucosa of the upper alimentary and respiratory tracts in rats.
PubMed: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.
PubMed: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.
PubMed:Determination of 2,6-dimethylaniline and o-toluidine impurities in preparations for local anaesthesia by the HPLC method with amperometric detection.
PubMed:The effect of deuterium and fluorine substitution upon the mutagenicity of N-hydroxy-2,6-dimethylaniline.
PubMed:Involvement of liver carboxylesterases in the in vitro metabolism of lidocaine.
PubMed:Lack of DNA binding in the rat nasal mucosa and other tissues of the nasal toxicants roflumilast, a phosphodiesterase 4 inhibitor, and a metabolite, 4-amino-3,5-dichloropyridine, in contrast to the nasal carcinogen 2,6-dimethylaniline.
PubMed:Analysis of the lidocaine metabolite 2,6-dimethylaniline in bovine and human milk.
PubMed:Immunohistochemical and ultrastructural studies of 2,6-dimethylaniline-induced nasal proliferative lesions in a rat two-stage nasal carcinogenesis model initiated with N-bis(2-hydroxypropyl)nitrosamine.
PubMed:Oxidation of 2,6-dimethylaniline by recombinant human cytochrome P450s and human liver microsomes.
PubMed:Plasma levels of lidocaine and prilocaine after application of Oraqix, a new intrapocket anesthetic, in patients with advanced periodontitis.
PubMed:Synthesis, characterization, and comparative 32P-postlabeling efficiencies of 2,6-dimethylaniline-DNA adducts.
PubMed:Identification of impurities in technical metalaxyl.
PubMed:Sequential observation of 2,6-dimethylaniline-induced nasal lesions in a rat two-stage nasal carcinogenesis model after initiation with N-bis(2-hydroxypropyl) nitrosamine.
PubMed:High-performance liquid chromatography-tandem electrospray mass spectrometry for the determination of lidocaine and its metabolites in human plasma and urine.
PubMed:Toxicity and blood concentrations of xylazine and its metabolite, 2,6-dimethylaniline, in rats after single or continuous oral administrations.
PubMed:Tumor-promoting activity of 2,6-dimethylaniline in a two-stage nasal carcinogenesis model in N-bis(2-hydroxypropyl)nitrosamine-treated rats.
PubMed:Studies on sulfation of synthesized metabolites from the local anesthetics ropivacaine and lidocaine using human cloned sulfotransferases.
PubMed:The regulatory status of xylazine for use in food-producing animals in the United States.
PubMed:An update of the National Toxicology Program database on nasal carcinogens.
PubMed:Pharmacokinetics and metabolism of the novel anticonvulsant agent N-(2,6-dimethylphenyl)-5-methyl-3-isoxazolecarboxamide (D2624) in rats and humans.
PubMed:Identification of 2,6-xylidine as a major lidocaine metabolite in human liver slices.
PubMed:Metabolism and excretion of ropivacaine in humans.
PubMed:Validation of high-performance liquid chromatographic methods on two silica base-deactivated reversed phases for the determination of chloroprocaine and bupivacaine.
PubMed:Determination of combined residues of metalaxyl and 2,6-dimethylaniline metabolites in urine by gas chromatography/mass spectrometry.
PubMed:2,6-Dimethylaniline--hemoglobin adducts from lidocaine in humans.
PubMed:Take the pain? Lidocaine comes under suspicion as a carcinogen.
PubMed:Simultaneous determination of xylazine and its major metabolite, 2,6-dimethylaniline, in bovine and swine kidney by liquid chromatography.
PubMed:Transformation of BALB/c-3T3 cells: IV. Rank-ordered potency of 24 chemical responses detected in a sensitive new assay procedure.
PubMed:2,6-Dimethylaniline (2,6-xylidine).
PubMed:Fluorescence polarization immunoassay and HPLC assays compared for measuring monoethylglycinexylidide in liver-transplant patients.
PubMed:Effects of parenteral nutrition on hepatic elimination of lidocaine: a study using the isolated perfused rat liver.
PubMed:The evaluation of a multiple dosing protocol for the mouse bone-marrow micronucleus assay using benzidine and 2,6-xylidine.
PubMed:Quantification of three lidocaine metabolites and their conjugates.
PubMed:NTP Toxicology and Carcinogenesis Studies of 2,6-Xylidine (2,6-Dimethylaniline) (CAS No. 87-62-7) in Charles River CD Rats (Feed Studies).
PubMed:The in vivo oxidative metabolism of 2,4- and 2,6-dimethylaniline in the dog and rat.
PubMed:Measurement of unscheduled DNA synthesis and S-phase synthesis in rodent hepatocytes following in vivo treatment: testing of 24 compounds.
PubMed:Covalent binding of [14C]-2,6-dimethylaniline to DNA of rat liver and ethmoid turbinate.
PubMed:[Amino acid derivatives of 2,6-xylidine and p-aminobenzoic acid. II. Synthesis of derivatives of N-(p-aminobenzoylaminoalkylacyl)-2,6-xylidines and study of their resistance to proteolytic factors].
PubMed:[Amino acid derivatives of 2,6 and p-aminobenzoic acid. I. Synthesis of derivatives of 2,6-xylidine and various derivatives of PAB].
PubMed:The in vivo effect of 2,6-xylidine on induction of micronuclei in mouse bone marrow cells.
PubMed:In vivo metabolism of lidocaine in the rat. Isolation of urinary metabolites as pentafluorobenzoyl derivatives and their identification by combined gas chromatography-mass spectrometry.
PubMed:New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides.
PubMed:Determination and temperature effects of lidocaine (lignocaine) hydrochloride, epinephrine, methylparaben, 2,6-dimethylaniline, and p-hydroxybenzoic acid in USP lidocaine injection by ion-pair reversed-phase high pressure liquid chromatography.
PubMed:New antiarrhythmic agents. 5. alpha-Aminoaceto-2,6-xylidides with functionalized amide alkyl substituents.
PubMed:New antiarrhythmic agents. 2. Amide alkyl alpha-amino xylidides.
PubMed:Hepatic effects of xylidine isomers in rats.
PubMed:Micromethod for determination of meperidine in plasma.
PubMed:[Studies on Xipamide (4-chloro-5-sulfamoyl-2',6'-salicyloxylidide). Part 1: Physico-chemical and chemical properties (author's transl)].
 
Notes:
None found
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