T3DB: 2-Aminonaphthalene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (3)XML

Targets (3)

Record Information

Version

2.0

Creation Date

2014-08-29 05:53:29 UTC

Update Date

2014-12-24 20:26:42 UTC

Accession Number

T3D4213

Identification

Common Name

2-Aminonaphthalene

Class

Small Molecule

Description

2-Aminonaphthalene is an aromatic amine. It is used to make azo dyes. It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Aminonaphthalene is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by heating 2-naphthol with ammonium acetate to 270-280 °C. It forms odorless, colorless plates which melt at 111-112 °C. It gives no color with ferric chloride. When reduced by sodium in boiling amyl alcohol solution it forms alicyclic tetrahydro-3-naphthylamine, which has most of the properties of the aliphatic amines; it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO2CC6H4CH2CH2CO2H. Numerous sulfonic acidsderived from 2-aminonaphthalene are known. Of these, the delta-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs. 2-Aminonaphthalene is found in cigarette smoke and suspected to contribute to the development of bladder cancer.

Compound Type

Amine
Cigarette Toxin
Industrial/Workplace Toxin
Metabolite
Organic Compound
Synthetic Compound
Uremic Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
2-Amino-naphthalene
2-Aminonaftalen
2-Naftilamina
2-Naftylamin
2-Naftylamine
2-Naphthalamine
2-Naphthalenamine
2-Naphthylamin
2-Naphthylamine
6-Naphthylamine
beta-Naftalamin
beta-Naftilamina
beta-Naftylamin
beta-Naftyloamina
beta-Naphthylamin
beta-Naphthylamine
BNA
Fast Scarlet Base B
Naphthalen-2-amine
RCRA waste number U168
USAF CB-22

Chemical Formula

C₁₀H₉N

Average Molecular Mass

143.185 g/mol

Monoisotopic Mass

143.073 g/mol

CAS Registry Number

91-59-8

IUPAC Name

naphthalen-2-amine

Traditional Name

β naphthylamine

SMILES

NC1=CC2=CC=CC=C2C=C1

InChI Identifier

InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2

InChI Key

InChIKey=JBIJLHTVPXGSAM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthylamine (CHEBI:27878 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cell surface
Cytosol
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Nucleotide Excision Repair	SMP00478	map03420
Base excision repair	Not Available	map03410

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	113°C
Boiling Point	Not Available
Solubility	0.189 mg/mL at 25°C
LogP	2.28

Predicted Properties

Property	Value	Source
Water Solubility	0.78 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.13	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	4.25	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	0	ChemAxon
Refractivity	47.21 m³·mol⁻¹	ChemAxon
Polarizability	16.06 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-0900000000-ecc6ebe23a5149ac29ab	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
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0006-0900000000-3bf8f62c0092962b9755	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00mo-0900000000-6b5ffaafdf95402a6216	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-0900000000-f2a5e8fa4fb64851b8cb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0006-0900000000-25323b2ac58bb87e247a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0006-0900000000-5915a9d18f20364e4263	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0006-0900000000-f27ef67ece738ba35154	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-a6e33405c02f2304cfbe	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-bd6d778c87db23cece65	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-4900000000-116c74f287b9a1de7adf	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-a3754f2dae00f59bff44	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-a3754f2dae00f59bff44	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1900000000-7f97cf17cf9c604035f9	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-3139ad0a41b8c84bdbc8	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-3139ad0a41b8c84bdbc8	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0900000000-5f22983ec8ec75c4235d	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-e5d0ebf20455b6c0a953	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-e5d0ebf20455b6c0a953	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-5900000000-93808191814dc1b4eacc	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-2900000000-ba05510fe794c267d8ff	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans. (7)

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

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

27878

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D4213.pdf

General References

Armeli G: [Kidney neoplasm in a subject exposed to betanaphthylamine]. Med Lav. 1968 Jun-Jul;59(6):450-4. [5738992 ]
Martynenko AG, Romanenko AM, Kartasheva LA: [Effect of liver functional disorders on the development of betanaphthylamine-induced tumors of the bladder in dogs]. Patol Fiziol Eksp Ter. 1973 May-Jun;17(3):55-6. [4750976 ]
Mancuso TF, el-Attar AA: Cohort study of workers exposed to betanaphthylamine and benzidine. J Occup Med. 1967 Jun;9(6):277-85. [6026374 ]
Ma XH, Sun GQ, Zhao YH, Jia XM: [Study on the properties of a novel glycine amino peptidase from Actinomucor elegans]. Sheng Wu Gong Cheng Xue Bao. 2004 Jul;20(4):578-83. [15968992 ]
Bul'bulian MA: [An epidemiological study of the cancer morbidity in persons having industrial contact with carcinogenic amino compounds]. Vopr Onkol. 1991;37(3):275-9. [2031321 ]
Peluso M, Airoldi L, Armelle M, Martone T, Coda R, Malaveille C, Giacomelli G, Terrone C, Casetta G, Vineis P: White blood cell DNA adducts, smoking, and NAT2 and GSTM1 genotypes in bladder cancer: a case-control study. Cancer Epidemiol Biomarkers Prev. 1998 Apr;7(4):341-6. [9568791 ]
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Neuropeptide Y receptor type 5

General Function:: Peptide yy receptor activity
Specific Function:: Receptor for neuropeptide Y and peptide YY. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity. Seems to be associated with food intake. Could be involved in feeding disorders.
Gene Name:: NPY5R
Uniprot ID:: Q15761
Molecular Weight:: 50725.99 Da

References

McNally JJ, Youngman MA, Lovenberg TW, Nepomuceno D, Wilson S, Dax SL: N-acylated alpha-(3-pyridylmethyl)-beta-aminotetralin antagoinists of the human neuropeptide Y Y5 receptor. Bioorg Med Chem Lett. 2000 Aug 7;10(15):1641-3. [10937714 ]

Target Details

2. Sodium-dependent noradrenaline transporter

General Function:: Norepinephrine:sodium symporter activity
Specific Function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular Weight:: 69331.42 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	5.91 uM	NVS_TR_hNET	Novascreen

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

3. Aryl hydrocarbon receptor

General Function:: Transcription regulatory region dna binding
Specific Function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:: AHR
Uniprot ID:: P35869
Molecular Weight:: 96146.705 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	9.39 uM	Tox21_AhR	Tox21/NCGC

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

2-Aminonaphthalene (T3D4213)

Structure for T3D4213: 2-Aminonaphthalene

Targets

References

Binding/Activity Constants

References

Binding/Activity Constants

References