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Record Information
Version2.0
Creation Date2014-08-29 05:53:29 UTC
Update Date2014-12-24 20:26:42 UTC
Accession NumberT3D4213
Identification
Common Name2-Aminonaphthalene
ClassSmall Molecule
Description2-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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Aminonaphthalene is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative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
Thumb
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 FormulaC10H9N
Average Molecular Mass143.185 g/mol
Monoisotopic Mass143.073 g/mol
CAS Registry Number91-59-8
IUPAC Namenaphthalen-2-amine
Traditional Nameβ naphthylamine
SMILESNC1=CC2=CC=CC=C2C=C1
InChI IdentifierInChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2
InChI KeyInChIKey=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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell surface
  • Cytosol
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Nucleotide Excision RepairSMP00478 map03420
Base excision repairNot Availablemap03410
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point113°C
Boiling PointNot Available
Solubility0.189 mg/mL at 25°C
LogP2.28
Predicted Properties
PropertyValueSource
Water Solubility0.78 g/LALOGPS
logP2.3ALOGPS
logP2.13ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)4.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.21 m³·mol⁻¹ChemAxon
Polarizability16.06 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0900000000-ecc6ebe23a5149ac29abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-a6e33405c02f2304cfbeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-bd6d778c87db23cece65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-4900000000-116c74f287b9a1de7adfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-a3754f2dae00f59bff44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-a3754f2dae00f59bff44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-7f97cf17cf9c604035f9JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-2900000000-ba05510fe794c267d8ffJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (7)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB41802
PubChem Compound ID7057
ChEMBL IDCHEMBL278164
ChemSpider ID6790
KEGG IDC02227
UniProt IDNot Available
OMIM ID
ChEBI ID27878
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4213.pdf
General References
  1. Armeli G: [Kidney neoplasm in a subject exposed to betanaphthylamine]. Med Lav. 1968 Jun-Jul;59(6):450-4. [5738992 ]
  2. 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 ]
  3. Mancuso TF, el-Attar AA: Cohort study of workers exposed to betanaphthylamine and benzidine. J Occup Med. 1967 Jun;9(6):277-85. [6026374 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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
  1. 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 ]
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
TypeValueAssay TypeAssay Source
AC505.91 uMNVS_TR_hNETNovascreen
References
  1. 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 ]
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
TypeValueAssay TypeAssay Source
AC509.39 uMTox21_AhRTox21/NCGC
References
  1. 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 ]