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Identification
NameAniline
Accession NumberDB06728
TypeSmall Molecule
GroupsExperimental
DescriptionAniline, 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 Identifiers
  • Caswell No. 051C
  • RCRA waste no. U012
  • RCRA waste number U012
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Aniline hydrobromide
542-11-0
Thumb
  • InChI Key: KBPWECBBZZNAIE-UHFFFAOYSA-N
  • Monoisotopic Mass: 172.984012
  • Average Mass: 174.041
DBSALT001862
Categories
UNIISIR7XX2F1K
CAS number62-53-3
WeightAverage: 93.1265
Monoisotopic: 93.057849229
Chemical FormulaC6H7N
InChI KeyInChIKey=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
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
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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 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 )
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
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-a23bad3a5415210b8e58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-129ed2147aba87164399View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-9000000000-9e60a29bae11a3beb396View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kf-9000000000-8e5e6fec72fd720bd3bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0006-9000000000-e04550d3cafee77e6192View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-4a2ea8998eab06e3b7faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-002f-9000000000-041fc0d729e6308b36ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-004i-9000000000-c0f67277e0af76d5d6e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0fb9-9000000000-35b2093eb2c81ba07d17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-15d86b7cf94658003a7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-9000000000-fc34fd188d386065c4f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03dl-9000000000-fbed3991af3afeea3a79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-0bea53746f5bc30ab770View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0007-9000000000-971619ea8bd73637ba14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-2001822055db683e8999View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-9000000000-a5bc25b5010f2044b435View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0006-9000000000-8ab282b725391b0d9923View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kf-9000000000-4ba5d22a406245826ca0View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

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

US6121492
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 92:02.00*
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (49.7 KB)
Interactions
Drug Interactions
Drug
ClotrimazoleThe metabolism of Aniline can be decreased when combined with Clotrimazole.
Cyproterone acetateThe serum concentration of Aniline can be decreased when it is combined with Cyproterone acetate.
DisulfiramThe metabolism of Aniline can be decreased when combined with Disulfiram.
IsoniazidThe metabolism of Aniline can be decreased when combined with Isoniazid.
NicotineThe metabolism of Aniline can be decreased when combined with Nicotine.
TiclopidineThe metabolism of Aniline can be decreased when combined with Ticlopidine.
Food InteractionsNot Available

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 or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Comments
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Drug created on August 18, 2010 14:11 / Updated on August 17, 2016 12:24