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Identification
NameAniline
Accession NumberDB06728
TypeSmall Molecule
GroupsExperimental
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
SynonymLanguageCode
aminobenzeneNot AvailableNot Available
AminophenNot AvailableNot Available
AnilinCzechNot Available
AnilinaNot AvailableNot Available
Aniline hydrobromideNot AvailableNot Available
Aniline oilNot AvailableNot Available
Aniline oil, phenylamineNot AvailableNot Available
Aniline, acsNot AvailableNot Available
Aniline(S#299)-LiqNot AvailableNot Available
AnilinumNot AvailableNot Available
AnyvimNot AvailableNot Available
ArylamineNot AvailableNot Available
BenzamineNot AvailableNot Available
BenzenamineNot AvailableNot Available
Benzene, aminoNot AvailableNot Available
Benzene,amino (aniline)Not AvailableNot Available
BenzeneamineNot AvailableNot Available
BenzidamNot AvailableNot Available
BIDD:ER0581Not AvailableNot Available
Blue oilNot AvailableNot Available
C.I. Oxidation base 1Not AvailableNot Available
CI Oxidation Base 1Not AvailableNot Available
CyanolNot AvailableNot Available
D'anilineNot AvailableNot Available
HSDB 43Not AvailableNot Available
Huile d'anilineFrenchNot Available
KrystallinNot AvailableNot Available
KyanolNot AvailableNot Available
nchembio.257-comp9Not AvailableNot Available
phenylamineNot AvailableNot Available
PhenyleneamineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number62-53-3
WeightAverage: 93.1265
Monoisotopic: 93.057849229
Chemical FormulaC6H7N
InChI KeyPAYRUJLWNCNPSJ-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilines
Direct ParentAnilines
Alternative Parents
Substituents
  • Aniline
  • Primary aromatic amine
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.7538
CYP450 2D6 substrateNon-inhibitor0.889
CYP450 2C19 substrateNon-inhibitor0.615
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point-6 °CPhysProp
boiling point184.1 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS/MSLC-MSMS1D NMR2D NMR
References
Synthesis Reference

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

US6121492
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 92:02.00*
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (49.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

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Drug created on August 18, 2010 14:11 / Updated on September 16, 2013 18:04