Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:20 UTC
Update Date2014-12-24 20:21:23 UTC
Accession NumberT3D0232
Identification
Common Name4-Aminobiphenyl
ClassSmall Molecule
Description4-Aminobiphenyl is an amine derivative of biphenyl. It is used to manufacture azo dyes. It is a known human carcinogen and so it has been largely replaced by less toxic compounds. It is similar to benzidine.
Compound Type
  • Amine
  • Aromatic Hydrocarbon
  • Cigarette Toxin
  • Food Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(1,1'-Biphenyl)-4-amine
(4-phenyl-phenyl)-amine
4-Amino-1,1'-biphenyl
4-Aminodiphenyl
4-Biphenylamine
4-Biphenylamine hydrochloride
4-Biphenylylamine
4-Phenylaniline
Aminobiphenyl
Biphenyl-4-amine
Biphenyl-4-ylamine
Biphenylamine
p-Aminobiphenyl
p-Aminodiphenyl
p-Biphenylamine
p-Phenylaniline
p-Xenylamine
Paraaminodiphenyl
Xenylamine
[1,1'-Biphenyl]-4-amine
[1,1'-biphenyl]-4-ylamine
{[1,1'-Biphenyl]-4-amine}
Chemical FormulaC12H11N
Average Molecular Mass169.222 g/mol
Monoisotopic Mass169.089 g/mol
CAS Registry Number92-67-1
IUPAC Name4-phenylaniline
Traditional Name4-aminobiphenyl
SMILESNC1=CC=C(C=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2
InChI KeyInChIKey=DMVOXQPQNTYEKQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point53.5°C
Boiling PointNot Available
SolubilityNot Available
LogP2.86
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.89ALOGPS
logP2.79ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)4.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity55.89 m³·mol⁻¹ChemAxon
Polarizability19.49 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-6900000000-485d158d46307e7e68a3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-6900000000-485d158d46307e7e68a3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1900000000-7cc97adc9c729451bd04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ea4ddfd09aa02c5ce68dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-bf153c3905690bdc5b59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-3900000000-2b96b507b444a3cfbeffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-8b7346091e37cac9abd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-8b7346091e37cac9abd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-c5ddef1d7d563f1bb3d7View in MoNA
MSMass Spectrum (Electron Ionization)splash10-014i-5900000000-2d12ae7fb469d0456cacView in MoNA
Toxicity Profile
Route of ExposureOral (8) ; inhalation (8) ; dermal (8)
Mechanism of Toxicity4-Aminobiphenyl requires metabolic activation in order to exert its toxicity. This is catalyzed by N-hydroxylation via cytochrome P450 1A2, then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The metabolites of 4-aminobiphenyl may form adducts with DNA, inducing mutations. 4-Aminobiphenyl and its metabolites may also cross the placenta and have fetal effects. (1, 2, 3, 4)
Metabolism4-Aminobiphenyl exposure can be assayed by measuring the extent of adduct formation with hemoglobin. 4-Aminobiphenyl metabolism is catalyzed by N-hydroxylation via cytochrome P450 1A2. It is then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The urinary metabolites of 4-aminobiphenyl include 4-acetylaminobiphenyl, 4'-hydroxy-4-aminobiphenyl, 2'-hydroxy-4-acetylaminobiphenyl, 4'-hydroxy-4-acetylaminobiphenyl, 3'-hydroxy, 4'-methoxy-4-acetylaminobiphenyl, 4'-hydroxy, 3'-methoxy-4-acetylaminobiphenyl, and 3',4'-dihydroxy-4-acetylaminobiphenyl. (8, 4)
Toxicity ValuesLD50: 205 mg/kg (Oral, Mouse) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (9)
Uses/Sources4-Aminobiphenyl is used to manufacture azo dyes and is also found in tobacco smoke. (10, 2)
Minimum Risk LevelNot Available
Health Effects4-Aminobiphenyl is a known human carcinogen. It may also cause methemoglobinemia. (9, 8)
SymptomsSymptoms of 4-aminobiphenyl may include dyspnea, headache, dizziness, lethargy, and ataxia. (8)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB13195
PubChem Compound ID7102
ChEMBL IDCHEMBL44201
ChemSpider ID6835
KEGG IDC10998
UniProt IDNot Available
OMIM ID
ChEBI ID1784
BioCyc IDN-HYDROXY-4-AMINOBIPHENYL
CTD IDC006757
Stitch ID4-Aminobiphenyl
PDB IDNot Available
ACToR ID70
Wikipedia Link4-Aminobiphenyl
References
Synthesis ReferenceNot Available
MSDST3D0232.pdf
General References
  1. Coghlin J, Gann PH, Hammond SK, Skipper PL, Taghizadeh K, Paul M, Tannenbaum SR: 4-Aminobiphenyl hemoglobin adducts in fetuses exposed to the tobacco smoke carcinogen in utero. J Natl Cancer Inst. 1991 Feb 20;83(4):274-80. [1994056 ]
  2. Jiang X, Yuan JM, Skipper PL, Tannenbaum SR, Yu MC: Environmental tobacco smoke and bladder cancer risk in never smokers of Los Angeles County. Cancer Res. 2007 Aug 1;67(15):7540-5. [17671226 ]
  3. Landi MT, Zocchetti C, Bernucci I, Kadlubar FF, Tannenbaum S, Skipper P, Bartsch H, Malaveille C, Shields P, Caporaso NE, Vineis P: Cytochrome P4501A2: enzyme induction and genetic control in determining 4-aminobiphenyl-hemoglobin adduct levels. Cancer Epidemiol Biomarkers Prev. 1996 Sep;5(9):693-8. [8877060 ]
  4. Ozawa S, Katoh T, Inatomi H, Imai H, Kuroda Y, Ichiba M, Ohno Y: Association of genotypes of carcinogen-activating enzymes, phenol sulfotransferase SULT1A1 (ST1A3) and arylamine N-acetyltransferase NAT2, with urothelial cancer in a Japanese population. Int J Cancer. 2002 Dec 1;102(4):418-21. [12402313 ]
  5. Nakanishi H, Takeuchi S, Kato K, Shimizu S, Kobayashi K, Tatematsu M, Shirai T: Establishment and characterization of three androgen-independent, metastatic carcinoma cell lines from 3,2'-dimethyl-4-aminobiphenyl-induced prostatic tumors in F344 rats. Jpn J Cancer Res. 1996 Dec;87(12):1218-26. [9045956 ]
  6. Wiencke JK: DNA adduct burden and tobacco carcinogenesis. Oncogene. 2002 Oct 21;21(48):7376-91. [12379880 ]
  7. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  8. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  9. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  10. Wikipedia. 4-Aminobiphenyl. Last Updated 18 April 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

General Function:
Not Available
Specific Function:
Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
Gene Name:
FBF1
Uniprot ID:
Q8TES7
Molecular Weight:
125445.19 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. [11697451 ]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Coghlin J, Gann PH, Hammond SK, Skipper PL, Taghizadeh K, Paul M, Tannenbaum SR: 4-Aminobiphenyl hemoglobin adducts in fetuses exposed to the tobacco smoke carcinogen in utero. J Natl Cancer Inst. 1991 Feb 20;83(4):274-80. [1994056 ]
  2. Jiang X, Yuan JM, Skipper PL, Tannenbaum SR, Yu MC: Environmental tobacco smoke and bladder cancer risk in never smokers of Los Angeles County. Cancer Res. 2007 Aug 1;67(15):7540-5. [17671226 ]
  3. Landi MT, Zocchetti C, Bernucci I, Kadlubar FF, Tannenbaum S, Skipper P, Bartsch H, Malaveille C, Shields P, Caporaso NE, Vineis P: Cytochrome P4501A2: enzyme induction and genetic control in determining 4-aminobiphenyl-hemoglobin adduct levels. Cancer Epidemiol Biomarkers Prev. 1996 Sep;5(9):693-8. [8877060 ]
  4. Ozawa S, Katoh T, Inatomi H, Imai H, Kuroda Y, Ichiba M, Ohno Y: Association of genotypes of carcinogen-activating enzymes, phenol sulfotransferase SULT1A1 (ST1A3) and arylamine N-acetyltransferase NAT2, with urothelial cancer in a Japanese population. Int J Cancer. 2002 Dec 1;102(4):418-21. [12402313 ]