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
SMILES
NC1=CC=CC=C1
InChI
InChIKey=PAYRUJLWNCNPSJ-UHFFFAOYSA-N
InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
| 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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Absorption, metabolism, and disposition of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v., and dermal administration. | 1999 Dec |
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| Acute intoxication with aniline: detection of acetaminophen as aniline metabolite. | 2000 |
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| White blood cell DNA adducts and fruit and vegetable consumption in bladder cancer. | 2000 Feb |
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| The use of amino compounds for binding 2,4,6-trinitrotoluene in water. | 2001 |
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| Localized activation of m-calpain in migrating human umbilical vein endothelial cells stimulated by shear stress. | 2001 |
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| Prevention of uremic bone disease using calcimimetic compounds. | 2001 |
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| Naphthol-ASBI phosphate as a preferred substrate for tartrate-resistant acid phosphatase isoform 5b. | 2001 Apr |
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| 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 |
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| Determination of the levels of aromatic amines in indoor and outdoor air in Italy. | 2001 Apr |
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| Efficacy and safety of eltenac gel in the treatment of knee osteoarthritis. | 2001 Apr |
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| The effects of exogenous calcium buffers on the systolic calcium transient in rat ventricular myocytes. | 2001 Apr |
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| Protonation and deprotonation of TpOs(NHPh)Cl(2): an unusually inert amido ligand. | 2001 Apr 9 |
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| 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 |
|
| 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 |
|
| Studies on the effect of diadenlyated nucleotides on calcium mobilization and prostacyclin synthesis in bovine aortic endothelial cells. | 2001 Feb |
|
| Variation in enzymes of arylamine procarcinogen biotransformation among bladder cancer patients and control subjects. | 2001 Feb |
|
| Elevation of intracellular calcium levels contributes to the inhibition of nitric oxide production by atrial natriuretic peptide. | 2001 Feb |
|
| Melatonin protects against ischaemic-reperfusion myocardial damage. | 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 |
|
| Induction of liver preneoplastic lesions by aminophenylnorharman, formed from norharman and aniline, in male F344 rats. | 2001 Feb 26 |
|
| Extracellular calcium-sensing receptor is expressed in rat hepatocytes. coupling to intracellular calcium mobilization and stimulation of bile flow. | 2001 Feb 9 |
|
| Increase in nuclear calcium in smooth muscle cells exposed to oxidized low density lipoprotein. | 2001 Jan |
|
| 4-[3-Bromo-4-hydroxyphenyl)amino]-6,7-dimethoxyquinazolin-1-ium chloride methanol solvate and 4-[(3-hydroxyphenyl)amino]-6,7-dimethoxy-1-quinazolinium chloride. | 2001 Jan |
|
| Loss of heterozygosity frequency at the Trp53 locus in p53-deficient (+/-) mouse tumors is carcinogen-and tissue-dependent. | 2001 Jan |
|
| Chromosome 11 allelotypes reflect a mechanism of chemical carcinogenesis in heterozygous p53-deficient mice. | 2001 Jan |
|
| Criteria for calcimimetic agent in the treatment of more severe secondary hyperparathyroidism. | 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 |
|
| Stark effects in gas-phase electronic spectra. Dipole moment of aniline in its excited S(1) state. | 2001 Jan 10 |
|
| Ribosomal proteins S3a, S13, S16, and S24 are not mutated in patients with Diamond-Blackfan anemia. | 2001 Jan 15 |
|
| A low-power, atmospheric pressure, pulsed plasma source for molecular emission spectrometry. | 2001 Jan 15 |
|
| Inhibition of stimulated Jurkat cell adenosine 3',5'-cyclic monophosphate synthesis by the immunomodulatory compound HR325. | 2001 Jan 15 |
|
| Palladium-catalyzed amination of aryl bromides and aryl triflates using diphosphane ligands: a kinetic study. | 2001 Jan 19 |
|
| Use of a Salmonella microsuspension bioassay to detect the mutagenicity of munitions compounds at low concentrations. | 2001 Jan 25 |
|
| Capillary zone electrophoresis of basic analytes in methanol as non-aqueous solvent mobility and ionisation constant. | 2001 Jan 5 |
|
| Partial degradation of p-aminoazobenzene by a defined mixed culture of Bacillus subtilis and Stenotrophomonas maltophilia. | 2001 Jan 5 |
|
| Synthesis of a novel series of cytotoxic bisindole alkaloids. | 2001 Jan 8 |
|
| Allosteric inhibition of fructose-1,6-bisphosphatase by anilinoquinazolines. | 2001 Jan 8 |
|
| 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 |
|
| 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 |
|
| Synthesis and Src kinase inhibitory activity of a series of 4-phenylamino-3-quinolinecarbonitriles. | 2001 Mar 1 |
|
| Bimetallic reactivity. On the use of oxadiazoles as binucleating ligands. | 2001 Mar 12 |
|
| Formaldehyde-mediated modification of natural deoxyguanosine with amines: one-pot cyclization as a molecular model for genotoxicity. | 2001 Mar 12 |
Sample Use Guides
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
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| Record UNII |
SIR7XX2F1K
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| Record Status |
Validated (UNII)
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EPA PESTICIDE CODE |
251400
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IARC | Aniline |
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100000126079
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C023650
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17296
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43
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SUB33422
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6115
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1441546
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62-53-3
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M1922
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1036110
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SIR7XX2F1K
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DB06728
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ANILINE
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DTXSID8020090
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200-539-3
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SIR7XX2F1K
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
