Aniline

Identification

Name
Aniline
Accession Number
DB06728
Type
Small Molecule
Groups
Experimental
Description

Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane. Like most volatile amines, it possesses the somewhat unpleasant odour of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. Aniline is colorless, but it slowly oxidizes and resinifies in air, giving a red-brown tint to aged samples.

Structure
Thumb
Synonyms
  • Aminobenzene
  • Aminophen
  • Anilin
  • Anilina
  • Aniline oil
  • Anilinum
  • Benzenamine
  • Benzeneamine
  • Fentanyl impurity F
  • Huile d'aniline
  • Kyanol
  • Phenylamine
  • Trimethoprim specified impurity K
External IDs
Caswell No. 051C / RCRA waste no. U012 / RCRA waste number U012
Product Ingredients
IngredientUNIICASInChI Key
Aniline acetate9K3OS48D34 542-14-3FHSWXOCOMAVQKE-UHFFFAOYSA-N
Aniline hydrobromide01XK3D1SXO 542-11-0KBPWECBBZZNAIE-UHFFFAOYSA-N
Aniline hydrochloride576R1193YL 142-04-1MMCPOSDMTGQNKG-UHFFFAOYSA-N
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
Not Available
Categories
UNII
SIR7XX2F1K
CAS number
62-53-3
Weight
Average: 93.1265
Monoisotopic: 93.057849229
Chemical Formula
C6H7N
InChI Key
PAYRUJLWNCNPSJ-UHFFFAOYSA-N
InChI
InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
IUPAC Name
aniline
SMILES
NC1=CC=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UKallikrein-1Not AvailableHuman
USerum albuminNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
ClotrimazoleThe metabolism of Aniline can be decreased when combined with Clotrimazole.Approved, Vet Approved
Cyproterone acetateThe serum concentration of Aniline can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DisulfiramThe metabolism of Aniline can be decreased when combined with Disulfiram.Approved
IsoniazidThe metabolism of Aniline can be decreased when combined with Isoniazid.Approved
NicotineThe metabolism of Aniline can be decreased when combined with Nicotine.Approved
TiclopidineThe metabolism of Aniline can be decreased when combined with Ticlopidine.Approved
Food Interactions
Not Available

References

Synthesis Reference

Michel Dury, "Method for preparing 2-trifluoro-methoxy-aniline." U.S. Patent US6121492, issued 0000.

US6121492
General References
Not Available
External Links
Human Metabolome Database
HMDB03012
KEGG Compound
C00292
PubChem Compound
6115
PubChem Substance
99443274
ChemSpider
5889
BindingDB
92572
ChEBI
17296
ChEMBL
CHEMBL538
HET
ANL
Wikipedia
Aniline
ATC Codes
Not Available
AHFS Codes
  • 92:02.00*
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (49.7 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)-6 °CPhysProp
boiling point (°C)184.1 °CPhysProp
water solubility3.6E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.90HANSCH,C ET AL. (1995)
pKa4.6 (at 25 °C)PERRIN,DD (1972)
Predicted Properties
PropertyValueSource
Water Solubility18.0 mg/mLALOGPS
logP0.89ALOGPS
logP1.14ChemAxon
logS-0.71ALOGPS
pKa (Strongest Basic)4.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.76 m3·mol-1ChemAxon
Polarizability10.29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9849
Blood Brain Barrier+0.9546
Caco-2 permeable+0.8816
P-glycoprotein substrateNon-substrate0.8908
P-glycoprotein inhibitor INon-inhibitor0.9864
P-glycoprotein inhibitor IINon-inhibitor0.9856
Renal organic cation transporterNon-inhibitor0.8716
CYP450 2C9 substrateNon-substrate0.8594
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.8107
CYP450 1A2 substrateNon-inhibitor0.5372
CYP450 2C9 inhibitorNon-inhibitor0.7538
CYP450 2D6 inhibitorNon-inhibitor0.889
CYP450 2C19 inhibitorNon-inhibitor0.615
CYP450 3A4 inhibitorNon-inhibitor0.9558
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7944
Ames testNon AMES toxic0.7047
CarcinogenicityCarcinogens 0.5
BiodegradationNot ready biodegradable0.5917
Rat acute toxicity2.5399 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9567
hERG inhibition (predictor II)Non-inhibitor0.9589
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00kf-9000000000-9a543eee5081cc927e82
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-e04550d3cafee77e6192
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-b4213ef5f8ee4a3df612
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-1900000000-b5d970641bbe63fdb366
LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-a23bad3a5415210b8e58
LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-004i-9000000000-129ed2147aba87164399
LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0udi-9000000000-9e60a29bae11a3beb396
LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-00kf-9000000000-8e5e6fec72fd720bd3bb
LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , PositiveLC-MS/MSsplash10-0006-9000000000-e04550d3cafee77e6192
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0006-9000000000-4a2ea8998eab06e3b7fa
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-002f-9000000000-041fc0d729e6308b36ec
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-004i-9000000000-c0f67277e0af76d5d6e1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0fb9-9000000000-35b2093eb2c81ba07d17
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-004i-9000000000-15d86b7cf94658003a7c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-03di-9000000000-fc34fd188d386065c4f5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-03dl-9000000000-fbed3991af3afeea3a79
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0006-9000000000-0bea53746f5bc30ab770
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0007-9000000000-971619ea8bd73637ba14
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0006-9000000000-2001822055db683e8999
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0006-9000000000-a5bc25b5010f2044b435
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0006-9000000000-8ab282b725391b0d9923
LC-MS/MS Spectrum - , negativeLC-MS/MSsplash10-00di-0900000000-ed34a4f0bafc3ce06174
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-4a2ea8998eab06e3b7fa
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted LC-MS/MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-00kf-9000000000-4ba5d22a406245826ca0
1H NMR Spectrum1D NMRNot applicable
1H NMR Spectrum1D NMRNot applicable
13C NMR Spectrum1D NMRNot applicable
[1H,13C] 2D NMR Spectrum2D NMRNot applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Aniline and substituted anilines
Direct Parent
Aniline and substituted anilines
Alternative Parents
Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aniline or substituted anilines / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Primary amine / Organonitrogen compound / Amine / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
primary arylamine, anilines (CHEBI:17296 ) / an arylamine (ANILINE )

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Glandular kallikreins cleave Met-Lys and Arg-Ser bonds in kininogen to release Lys-bradykinin.
Gene Name
KLK1
Uniprot ID
P06870
Uniprot Name
Kallikrein-1
Molecular Weight
28889.425 Da
References
  1. Sousa MO, Miranda TL, Costa EB, Bittar ER, Santoro MM, Figueiredo AF: Linear competitive inhibition of human tissue kallikrein by 4-aminobenzamidine and benzamidine and linear mixed inhibition by 4-nitroaniline and aniline. Braz J Med Biol Res. 2001 Jan;34(1):35-44. [PubMed:11151026 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Thier R, Lewalter J, Selinski S, Bolt HM: Biological monitoring in workers in a nitrobenzene reduction plant: haemoglobin versus serum albumin adducts. Int Arch Occup Environ Health. 2001 Sep;74(7):483-8. [PubMed:11697451 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Drug created on August 18, 2010 14:11 / Updated on September 01, 2017 11:30