T3DB: 4-Aminobiphenyl

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2009-03-06 18:58:20 UTC

Update Date

2014-12-24 20:21:23 UTC

Accession Number

T3D0232

Identification

Common Name

4-Aminobiphenyl

Class

Small Molecule

Description

4-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

MOL SDF PDB SMILES InChI

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 Formula

C₁₂H₁₁N

Average Molecular Mass

169.222 g/mol

Monoisotopic Mass

169.089 g/mol

CAS Registry Number

92-67-1

IUPAC Name

[1,1'-biphenyl]-4-amine

Traditional Name

4-aminobiphenyl

SMILES

NC1=CC=C(C=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2

InChI Key

InChIKey=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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aminobiphenyl (CHEBI:1784 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

carcinogenic agent

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	53.5°C
Boiling Point	Not Available
Solubility	Not Available
LogP	2.86

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.89	ALOGPS
logP	2.79	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	4.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	55.89 m³·mol⁻¹	ChemAxon
Polarizability	19.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-6900000000-485d158d46307e7e68a3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-6900000000-485d158d46307e7e68a3	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1900000000-7cc97adc9c729451bd04	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-ea4ddfd09aa02c5ce68d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-bf153c3905690bdc5b59	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-3900000000-2b96b507b444a3cfbeff	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-8b7346091e37cac9abd9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-8b7346091e37cac9abd9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2900000000-c5ddef1d7d563f1bb3d7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-f04809ed8d3ffdb9e395	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-f04809ed8d3ffdb9e395	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-0900000000-b4d0aef74055dd87486f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-c8884063706b25aca801	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-c8884063706b25aca801	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-0e190a36e93b266cb602	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-5900000000-2d12ae7fb469d0456cac	2014-09-20	View Spectrum

Toxicity Profile

Route of Exposure

Oral (8) ; inhalation (8) ; dermal (8)

Mechanism of Toxicity

4-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)

Metabolism

4-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 Values

LD50: 205 mg/kg (Oral, Mouse) (7)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans. (9)

Uses/Sources

4-Aminobiphenyl is used to manufacture azo dyes and is also found in tobacco smoke. (10, 2)

Minimum Risk Level

Not Available

Health Effects

4-Aminobiphenyl is a known human carcinogen. It may also cause methemoglobinemia. (9, 8)

Symptoms

Symptoms of 4-aminobiphenyl may include dyspnea, headache, dizziness, lethargy, and ataxia. (8)

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

1784

BioCyc ID

N-HYDROXY-4-AMINOBIPHENYL

CTD ID

C006757

Stitch ID

4-Aminobiphenyl

PDB ID

Not Available

ACToR ID

Wikipedia Link

4-Aminobiphenyl

References

Synthesis Reference

Not Available

MSDS

T3D0232.pdf

General References

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 ]
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 ]
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 ]
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 ]
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 ]
Wiencke JK: DNA adduct burden and tobacco carcinogenesis. Oncogene. 2002 Oct 21;21(48):7376-91. [12379880 ]
Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Wikipedia. 4-Aminobiphenyl. Last Updated 18 April 2009. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Gene	Gene Symbol	Gene ID	Interaction	Chromosome	Details

Targets

Target Details

1. Fas-binding factor 1

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

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

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 ]
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 ]
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 ]
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 ]

4-Aminobiphenyl (T3D0232)

Structure for T3D0232: 4-Aminobiphenyl

Targets

References

References