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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
Determination of the levels of aromatic amines in indoor and outdoor air in Italy.
2001 Apr
The utilization of aniline, chlorinated aniline, and aniline blue as the only source of nitrogen by fungi in water.
2001 Apr
Protonation and deprotonation of TpOs(NHPh)Cl(2): an unusually inert amido ligand.
2001 Apr 9
Polyaniline-dacron composite as solid phase in enzyme linked immunosorbent assay for Yersinia pestis antibody detection.
2001 Aug
5-HT(6) receptor antagonists: lead optimisation and biological evaluation of N-aryl and N-heteroaryl 4-amino-benzene sulfonamides.
2001 Feb
The lipid charge density at the bilayer surface modulates the effects of melittin on membranes.
2001 Feb
Vibrational overtone spectra of chloroanilines--evidence for intramolecular hydrogen bonding in o-chloroaniline.
2001 Feb
Coordinated control of cell Ca(2+) loading and triggered release from the sarcoplasmic reticulum underlies the rapid inotropic response to increased L-type Ca(2+) current.
2001 Feb 2
The influence of substituent groups on the resonance stabilization of benzene. An ab initio computational study.
2001 Feb 23
Extracellular calcium-sensing receptor is expressed in rat hepatocytes. coupling to intracellular calcium mobilization and stimulation of bile flow.
2001 Feb 9
[Collecting of trichloroaniline in the air by micropore filter membrane and determination by gas chromatography].
2001 Jan
N-nitrosoanilines: a new class of caspase-3 inhibitors.
2001 Jan
Loss of heterozygosity frequency at the Trp53 locus in p53-deficient (+/-) mouse tumors is carcinogen-and tissue-dependent.
2001 Jan
Role of calcium-dependent protease(s) in globulization of isolated rat lens cortical fiber cells.
2001 Jan
Role of meiosis-activating sterols in rat oocyte maturation: effects of specific inhibitors and changes in the expression of lanosterol 14alpha-demethylase during the preovulatory period.
2001 Jan
Direct visualization of sarcoplasmic reticulum regions discharging Ca(2+)sparks in vascular myocytes.
2001 Jan
Adenosine A1 receptor activation reduces reactive oxygen species and attenuates stunning in ventricular myocytes.
2001 Jan
Heterogeneity of calcium stores and elementary release events in canine pulmonary arterial smooth muscle cells.
2001 Jan
A low-power, atmospheric pressure, pulsed plasma source for molecular emission spectrometry.
2001 Jan 15
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
Formaldehyde-mediated modification of natural deoxyguanosine with amines: one-pot cyclization as a molecular model for genotoxicity.
2001 Mar 12
Binding of substituted phenol and aniline derivatives to the corn protein zein studied by high-performance liquid chromatography.
2001 Mar 25
High-resolution crystal structure of deoxy hemoglobin complexed with a potent allosteric effector.
2001 May
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 15 15:51:16 GMT 2023
Edited
by admin
on Fri Dec 15 15:51:16 GMT 2023
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 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
IARC Aniline
Code System Code Type Description
SMS_ID
100000126079
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
MESH
C023650
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
CHEBI
17296
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
HSDB
43
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
EVMPD
SUB33422
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
PUBCHEM
6115
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
RXCUI
1441546
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY RxNorm
CAS
62-53-3
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
MERCK INDEX
m1922
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1036110
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
FDA UNII
SIR7XX2F1K
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
DRUG BANK
DB06728
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
WIKIPEDIA
ANILINE
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID8020090
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-539-3
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
DAILYMED
SIR7XX2F1K
Created by admin on Fri Dec 15 15:51:17 GMT 2023 , Edited by admin on Fri Dec 15 15:51:17 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
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
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
EP
Related Record Type Details
ACTIVE MOIETY