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Details

Stereochemistry ACHIRAL
Molecular Formula C6H7N
Molecular Weight 93.1265
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANILINE

SMILES

NC1=CC=CC=C1

InChI

InChIKey=PAYRUJLWNCNPSJ-UHFFFAOYSA-N
InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2

HIDE SMILES / InChI

Molecular Formula C6H7N
Molecular Weight 93.1265
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Aniline is a toxic organic compound consisting of a phenyl group attached to an amino group. It is the prototypical aromatic amine. Aniline and its derivatives are very important for the synthesis of chemical products such as dyes, resins, and medicines. The main use of aniline is in the manufacture of precursors to polyurethane. Aniline is a carcinogen that is considered to induce tumors secondary to hemosiderosis as a consequence of methemoglobinemia. Aniline is classified as Group 3, not classifiable as to its carcinogenicity in humans (IARC, 480 1987b). Aniline occurs naturally in some foods (i.e., corn, grains, beans, and tea), but the larger source of exposure is in industrial settings. Lifetime permissible daily exposure (PDE) for aniline is 720 ug/day. Simple anilines such as aniline and monosubstituted anilines are known to disappear from the environment mainly via biodegradation.

Originator

Sources: Otto Unverdorben (1826). 'Ueber das Verhalten der organischen Körper in höheren Temperaturen' [On the behaviour of organic substances at high temperatures]. Annalen der Physik und Chemie. 8 (11): 397–410.
Curator's Comment: Aniline was first isolated in 1826 by Otto Unverdorben by destructive distillation of indigo

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Biological activity of some 4-anilinoquinazolines: cytotoxic, genotoxic and antiprotease effects, induction of necrosis and changes of actin cytoskeleton.
2001
Assessment of chloroaniline toxicity by the submitochondrial particle assay.
2001 Apr
Exposure to 4,4'-methylenediphenyl diisocyanate (MDI) during moulding of rigid polyurethane foam: determination of airborne MDI and urinary 4,4'-methylenedianiline (MDA).
2001 Apr
Pharmacogenetic profile of xenobiotic enzyme metabolism in survivors of the Spanish toxic oil syndrome.
2001 Apr
Effects of novel phenylretinamides on cell growth and apoptosis in bladder cancer.
2001 Apr
Removal and recovery of p-phenylenediamines developing compounds from photofinishing lab-washwater using clinoptilolite tuffs from Greece.
2001 Apr
Naphthol-ASBI phosphate as a preferred substrate for tartrate-resistant acid phosphatase isoform 5b.
2001 Apr
T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome.
2001 Apr
Determination of the levels of aromatic amines in indoor and outdoor air in Italy.
2001 Apr
Efficacy and safety of eltenac gel in the treatment of knee osteoarthritis.
2001 Apr
The utilization of aniline, chlorinated aniline, and aniline blue as the only source of nitrogen by fungi in water.
2001 Apr
The effects of exogenous calcium buffers on the systolic calcium transient in rat ventricular myocytes.
2001 Apr
Analysis of the metabolites of the sodium salt of 6-hydroxy-5-(phenylazo)-2-naphthalenesulfonic acid in Sprague-Dawley rat urine.
2001 Apr 25
Phenylene ethynylene diazonium salts as potential self-assembling molecular devices.
2001 Apr 5
Characterisation using FLIPR of human vanilloid VR1 receptor pharmacology.
2001 Apr 6
Water-soluble propofol analogues with intravenous anaesthetic activity.
2001 Apr 9
Polyaniline-dacron composite as solid phase in enzyme linked immunosorbent assay for Yersinia pestis antibody detection.
2001 Aug
Differential effects of IH636 grape seed proanthocyanidin extract and a DNA repair modulator 4-aminobenzamide on liver microsomal cytochrome 4502E1-dependent aniline hydroxylation.
2001 Feb
The lipid charge density at the bilayer surface modulates the effects of melittin on membranes.
2001 Feb
Synthesis, characterization, and comparative 32P-postlabeling efficiencies of 2,6-dimethylaniline-DNA adducts.
2001 Feb
Studies on the effect of diadenlyated nucleotides on calcium mobilization and prostacyclin synthesis in bovine aortic endothelial cells.
2001 Feb
Determination of bromethalin in commercial rodenticides found in consumer product samples by HPLC-UV-vis spectrophotometry and HPLC-negative-ion APCI-MS.
2001 Feb
Multiple inhibitor analysis of the brequinar and leflunomide binding sites on human dihydroorotate dehydrogenase.
2001 Feb 20
The influence of substituent groups on the resonance stabilization of benzene. An ab initio computational study.
2001 Feb 23
Dansylation of hydroxyl and carboxylic acid functional groups.
2001 Feb 26
Inhibition kinetics of green crab (Scylla serrata) alkaline phosphatase by zinc ions: a new type of complexing inhibition.
2001 Feb 9
Storage time and deodorization temperature influence the formation of aniline-derived compounds in denatured rapeseed oils.
2001 Jan
[Collecting of trichloroaniline in the air by micropore filter membrane and determination by gas chromatography].
2001 Jan
Increase in nuclear calcium in smooth muscle cells exposed to oxidized low density lipoprotein.
2001 Jan
Stark effects in gas-phase electronic spectra. Dipole moment of aniline in its excited S(1) state.
2001 Jan 10
Palladium-catalyzed amination of aryl bromides and aryl triflates using diphosphane ligands: a kinetic study.
2001 Jan 19
[Clinical prognostic factors in superficial cancer of the urinary bladder].
2001 Mar
Dinitroaniline herbicides against protozoan parasites: the case of Trypanosoma cruzi.
2001 Mar
Cytotoxic effects of peroxynitrite, polymorphonuclear neutrophils, free-radical scavengers, inhibitors of myeloperoxidase, and inhibitors of nitric oxide synthase on bovine mammary secretory epithelial cells.
2001 Mar
Selective electrocatalytic oxidation of N-alkyl-N-methylanilines to N-alkylformanilides using nitroxyl radical.
2001 Mar
A high-throughput microtiter plate-based calcium assay for the study of protease-activated receptor 2 activation.
2001 Mar
Simulation of biological degradation of aromatic amines in river bed sediments.
2001 Mar
Optimization of force constants with an Urey-Bradley force field avoiding normal mode crossings.
2001 Mar 1
Structure of exciplexes: solvent and temperature dependences of charge transfer character.
2001 Mar 1
Synthesis and Src kinase inhibitory activity of a series of 4-phenylamino-3-quinolinecarbonitriles.
2001 Mar 1
Relationship of Ca2+ sparks to STOCs studied with 2D and 3D imaging in feline oesophageal smooth muscle cells.
2001 Mar 1
Formaldehyde-mediated modification of natural deoxyguanosine with amines: one-pot cyclization as a molecular model for genotoxicity.
2001 Mar 12
A phase I study of RSR13, a radiation-enhancing hemoglobin modifier: tolerance of repeated intravenous doses and correlation of pharmacokinetics with pharmacodynamics.
2001 Mar 15
Synthesis of functional aromatic multisulfonyl chlorides and their masked precursors.
2001 Mar 23
Evaluation of the gender differences in 4,4'-methylenedianiline toxicity, distribution, and effects on biliary parameters.
2001 Mar 23
Binding of substituted phenol and aniline derivatives to the corn protein zein studied by high-performance liquid chromatography.
2001 Mar 25
The use of surrogate endpoints to assess potential toxicity in humans.
2001 Mar 31
Predictive value of sperm chromatin condensation (aniline blue staining) in the assessment of male fertility.
2001 Mar-Apr
High-resolution crystal structure of deoxy hemoglobin complexed with a potent allosteric effector.
2001 May
Functional interrelationships in the alkaline phosphatase superfamily: phosphodiesterase activity of Escherichia coli alkaline phosphatase.
2001 May 15
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
To understand the mechanisms of aniline biodegradation A. baylyi BD413 (formerly termed Acinetobacter sp. or Acinetobacter calcoaceticus) were inoculated into medium containing aniline as the sole carbon source and then cultivated with shaking. BD413 harboring pTB01 completely degraded 0.15 mM aniline within 1 day, as well as additional spikes of aniline administered day by day.
Substance Class Chemical
Created
by admin
on Fri Dec 16 18:24:24 UTC 2022
Edited
by admin
on Fri Dec 16 18:24:24 UTC 2022
Record UNII
SIR7XX2F1K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANILINE
HSDB   MART.   MI   USP-RS   WHO-DD  
Systematic Name English
ANILINE [INCI]
Common Name English
ANILINE [MI]
Common Name English
ANILINE [IARC]
Common Name English
ANILINUM
HPUS  
Common Name English
ANILINE OIL
Common Name English
ANILINE [USP-RS]
Common Name English
Aniline [WHO-DD]
Common Name English
FENTANYL IMPURITY F [EP IMPURITY]
Common Name English
TRIMETHOPRIM IMPURITY K [EP IMPURITY]
Common Name English
MESALAZINE IMPURITY K [EP IMPURITY]
Common Name English
ANILINUM [HPUS]
Common Name English
AMINOBENZOIC ACID IMPURITY C [EP IMPURITY]
Common Name English
AMINOBENZENE
Systematic Name English
PHENYLAMINE
Systematic Name English
BENZENAMINE
Systematic Name English
AMINOPHEN
Common Name English
ANILINE [MART.]
Common Name English
ANILINE [HSDB]
Common Name English
ANILINE [USP IMPURITY]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 251400
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
IARC Aniline
Code System Code Type Description
MESH
C023650
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
CHEBI
17296
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
HSDB
43
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
EVMPD
SUB33422
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
PUBCHEM
6115
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
RXCUI
1441546
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY RxNorm
CAS
62-53-3
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
MERCK INDEX
M1922
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY Merck Index
RS_ITEM_NUM
1036110
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
FDA UNII
SIR7XX2F1K
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
DRUG BANK
DB06728
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
WIKIPEDIA
ANILINE
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
EPA CompTox
DTXSID8020090
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-539-3
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
DAILYMED
SIR7XX2F1K
Created by admin on Fri Dec 16 18:24:24 UTC 2022 , Edited by admin on Fri Dec 16 18:24:24 UTC 2022
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY