2-Aminophenol (T3D3599)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (9)XML
Targets (9)
Record Information
Version2.0
Creation Date2009-11-11 22:17:57 UTC
Update Date2014-12-24 20:26:12 UTC
Accession NumberT3D3599
Identification
Common Name2-Aminophenol
ClassSmall Molecule
Description2-Aminophenol is an amphoteric molecule and a reducing agent. It is a useful reagent for the synthesis of dyes and heterocyclic compounds. As it is used synthesis of dyes, it can often be found in cosmetic products such as hair dyes. (5)
Compound Type
  • Amine
  • Aromatic Hydrocarbon
  • Cosmetic Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1-Amino-2-hydroxybenzene
1-Hydroxy-2-aminobenzene
2-Amino-1-hydroxybenzene
2-Amino-phenole
2-Aminobenzenol
2-AMINOPHENOL
2-Hydroxyanaline
2-Hydroxyaniline
Benzofur GG
Fouramine op
Nako Yellow 3GA
Nako yellow ga
O-aminophenol
O-hydroxyaniline
O-hydroxyphenylamine
Orsin
Ortho-aminophenol
Paradone olive green b
Pelagol 3GA
Pelagol grey GG
Questiomycin b
Chemical FormulaC6H7NO
Average Molecular Mass109.126 g/mol
Monoisotopic Mass109.053 g/mol
CAS Registry Number95-55-6
IUPAC Name2-aminophenol
Traditional Name2-aminophenol
SMILESNC1=CC=CC=C1O
InChI IdentifierInChI=1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2
InChI KeyInChIKey=CDAWCLOXVUBKRW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • O-aminophenol
  • Aniline or substituted anilines
  • Aminophenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite crystals. (5)
Experimental Properties
PropertyValue
Melting Point174°C
Boiling PointNot Available
Solubility20 mg/mL at 20°C
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility116 g/LALOGPS
logP0.35ALOGPS
logP0.84ChemAxon
logS0.02ALOGPS
pKa (Strongest Acidic)10.35ChemAxon
pKa (Strongest Basic)4.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability11.16 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-2940000000-25ee431a814318b5cd432014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-1391000000-c7b790c4abd26562c5152014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9500000000-64a0083db1618cc2d0302017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0930000000-dca6cf7ac4a910fdb0602017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0491000000-cee860404b79a1d6aa742017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-a46bd7617baf2869204e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03fr-9700000000-bb6fb8e53538176fc3a72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03dl-9600000000-a6223641aa5dc0380c022017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-9000000000-9a3dae6cbb045cbf75c32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9000000000-9bb70b310c6146ff4a8a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-db35f1e1ead0bce0ccea2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-2900000000-58d470a79c69d94741812017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-3900000000-b3cb0ba9cdf9ed8d746d2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-e58857d4114340490af92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-7900000000-6a7bea3115d2f232655f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9000000000-9088e18b362fd96700132016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-37cb1b0b0fd8587850302016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-40c5580a05dd723236472016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-5a42eb6db939ab0337f72016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-7900000000-518eb832be87964ec0c62014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4)
Mechanism of Toxicity2-Aminophenol interacts with both adult and fetal hemoglobin, forming methemoglobin. In comparison to its isomers, 3-aminophenol and 4-aminophenol, 2-aminophenol is the most effective in forming methemoglobin. Since methemoglobin cannot bind oxygen like hemoglobin can, elevated levels of methemoglobin cause a condition called methemoglobinemia, which can result in tissue hypoxia. (6, 1)
MetabolismNot Available
Toxicity ValuesLD50: 1250 mg/kg (Oral, Mouse) (2) LD50: 37 mg/kg (Subcutaneous), Rat) (2) LD50: 200 mg/kg (Intrapertioneal, Mouse) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAs a reducing agent, 2-Aminophenol is marketed under the names of Atomal and Ortol and used to develop black and white photographs. 2-Aminophenol is also an intermediate in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. (5)
Minimum Risk LevelNot Available
Health Effects2-Aminophenol may act as a skin sensitizer and cause contact dermatitis. In addition, inhalation of large amounts can cause methemoglobinemia and bronchial asthma. (3)
Symptoms2-Aminophenol may cause contact dermatitis. Signs and symptoms of methemoglobinemia may include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. Severe methemoglobinemia can result in dysrhythmias, seizures, coma, and death. (3, 6)
TreatmentMethemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution administered intravenously slowly over five minutes followed by IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (6)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01726
HMDB IDNot Available
PubChem Compound ID5801
ChEMBL IDCHEMBL28319
ChemSpider ID5596
KEGG IDC01987
UniProt IDNot Available
OMIM ID
ChEBI ID18112
BioCyc ID2-AMINOPHENOL
CTD IDC027667
Stitch IDo-aminophenol
PDB IDNot Available
ACToR ID375837
Wikipedia Link2-Aminophenol
References
Synthesis Reference

Theodor Papenfuhs, “Process for the preparation of 5-hydroxyethylsulfonyl-2-aminophenol (ethers).” U.S. Patent US4613704, issued February, 1979.

MSDST3D3599.pdf
General References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  3. Clayton GD and Clayton FE (eds) (1993-1994). Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc.
  4. HSDB: Hazardous Substances Data Bank. National Library of Medicine (2001). [Link]
  5. Wikipedia. 2-Aminophenol. Last Updated 12 June 2009. [Link]
  6. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

Target Details
1. Hemoglobin subunit alpha
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
2. Hemoglobin subunit beta
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:
HBB
Uniprot ID:
P68871
Molecular Weight:
15998.34 Da
References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
3. Hemoglobin subunit delta
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBD
Uniprot ID:
P02042
Molecular Weight:
16055.41 Da
References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
4. Hemoglobin subunit epsilon
General Function:
Oxygen transporter activity
Specific Function:
The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
Gene Name:
HBE1
Uniprot ID:
P02100
Molecular Weight:
16202.71 Da
References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
5. Hemoglobin subunit gamma-1
General Function:
Oxygen transporter activity
Specific Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Gene Name:
HBG1
Uniprot ID:
P69891
Molecular Weight:
16140.37 Da
References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
6. Hemoglobin subunit gamma-2
General Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Specific Function:
Heme binding
Gene Name:
HBG2
Uniprot ID:
P69892
Molecular Weight:
16126.35 Da
References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
7. Hemoglobin subunit mu
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBM
Uniprot ID:
Q6B0K9
Molecular Weight:
15617.97 Da
References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
8. Hemoglobin subunit theta-1
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBQ1
Uniprot ID:
P09105
Molecular Weight:
15507.575 Da
References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
9. Hemoglobin subunit zeta
General Function:
Oxygen transporter activity
Specific Function:
The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
Gene Name:
HBZ
Uniprot ID:
P02008
Molecular Weight:
15636.845 Da
References
  1. Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]