Tmic
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Record Information
Version2.0
Creation Date2009-11-11 22:22:53 UTC
Update Date2014-12-24 20:26:12 UTC
Accession NumberT3D3601
Identification
Common Name3-Aminophenol
ClassSmall Molecule
Description3-Aminophenol is an amphoteric molecule and a reducing agent. Aminophenols are intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. (6)
Compound Type
  • Amine
  • Aromatic Hydrocarbon
  • Cosmetic Toxin
  • Household Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
-hydroxybenzenamine
1-Amino-3-hydroxybenzene
3-Amino-1-hydroxybenzene
3-Hydroxyaniline
3-Hydroxyanilinel AC
3-Hydroxybenzenamine
Basf ursol eg
Fouramine eg
Fourrine 65
Fourrine eg
Furro eg
Futramine eg
M-aminofenol
M-aminophenol
M-hydroxyaminobenzene
M-hydroxyaniline
M-hydroxyphenylamine
Nako teg
Pelagol eg
Renal eg
Rodinal
Tertral eg
Ursol eg
Chemical FormulaC6H7NO
Average Molecular Mass109.126 g/mol
Monoisotopic Mass109.053 g/mol
CAS Registry Number591-27-5
IUPAC Name3-aminophenol
Traditional Namem-aminophenol
SMILESNC1=CC=CC(O)=C1
InChI IdentifierInChI=1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2
InChI KeyInChIKey=CWLKGDAVCFYWJK-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
  • M-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 RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point123°C
Boiling PointNot Available
Solubility27 mg/mL at 20°C
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility98.3 g/LALOGPS
logP0.43ALOGPS
logP0.84ChemAxon
logS-0.05ALOGPS
pKa (Strongest Acidic)9.82ChemAxon
pKa (Strongest Basic)4.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability11.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-e51735a6e5d4a3e5eeadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-09d13b69959de03f7d24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-6803b31dff294a8f675cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-81db2f962b909ae3bce5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-440dd43ef196996903c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-f0a2d17e6f8da98a7b0aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-7900000000-6422996aedcba7475ca2View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4)
Mechanism of Toxicity3-Aminophenol interacts with both adult and fetal hemoglobin, forming methemoglobin. In comparison to its isomers, 2-aminophenol and 4-aminophenol, 3-aminophenol is the least 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. (5, 1)
MetabolismNot Available
Toxicity ValuesLD50: 150 mg/kg (Intraperitoneal, Mouse) (2) LD50: 750 mg/kg (Oral, Quail) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAminophenols are also intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. (6)
Minimum Risk LevelNot Available
Health Effects3-Aminophenol may act as a skin sensitizer and cause contact dermatitis. In addition, inhalation of large amounts can cause methemoglobinemia and bronchial asthma. (3)
Symptoms3-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, 5)
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. (5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID11568
ChEMBL IDCHEMBL269755
ChemSpider ID11080
KEGG IDC05058
UniProt IDNot Available
OMIM ID
ChEBI ID28924
BioCyc IDCPD-10489
CTD IDC055528
Stitch IDm-aminophenol
PDB IDNot Available
ACToR ID219691
Wikipedia Link3-Aminophenol
References
Synthesis ReferenceNot Available
MSDST3D3601.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. Methemoglobinemia. Last Updated 22 July 2009. [Link]
  6. Wikipedia. 2-Aminophenol. Last Updated 12 June 2009. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

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]
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]
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]
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]
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]
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]
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]
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]
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]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular Weight:
28870.0 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory4.9 uMNot AvailableBindingDB 50428384
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA12
Uniprot ID:
O43570
Molecular Weight:
39450.615 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory7.7 uMNot AvailableBindingDB 50428384
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
General Function:
Metal ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA14
Uniprot ID:
Q9ULX7
Molecular Weight:
37667.37 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory7.2 uMNot AvailableBindingDB 50428384
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
General Function:
Zinc ion binding
Specific Function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular Weight:
29245.895 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory4.7 uMNot AvailableBindingDB 50428384
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA7
Uniprot ID:
P43166
Molecular Weight:
29658.235 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory5.9 uMNot AvailableBindingDB 50428384
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
Gene Name:
CA9
Uniprot ID:
Q16790
Molecular Weight:
49697.36 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory4.9 uMNot AvailableBindingDB 50428384
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]