Showing Compound Card for m-Aminophenol (CDB005672)

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Record Information
Version1.0
Created at2020-04-27 16:44:08 UTC
Updated at2021-01-04 18:49:07 UTC
CannabisDB IDCDB005672
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namem-Aminophenol
Description3-Aminophenol, also known as m-hydroxyaniline, belongs to the class of organic compounds known as anilines and substituted anilines. These are organic compounds containing an aminobenzene moiety. 3-Aminophenol is also classified as an aromatic amine and an aromatic alcohol. 3-Aminophenol is used in the synthesis of 3-(diethylamino)phenol, a key intermediate for the preparation of several fluorescent dyes (e.g., rhodamine B). Other uses for 3-Aminophenol include hair dye colorants and stabilizers for chlorine-containing thermoplastics. Aminophenols are intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. Inhalation of large amounts of 3-Aminophenol can cause methemoglobinemia and bronchial asthma. Signs and symptoms of methemoglobinemia may include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. In comparison to its isomers, 2-aminophenol and 4-aminophenol, 3-aminophenol is the least effective in forming methemoglobin. 3-Aminophenol may cause contact dermatitis (PMID: 29574799 ). 3-Aminophenol is a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
m-AminophenolChEBI
m-HydroxyanilineChEBI
3-HydroxyanilineKegg
3-Aminophenol monopotassium saltMeSH
3-Aminophenol hydrochlorideMeSH
3-Aminophenol acetateMeSH
3-Aminophenol monosodium saltMeSH
3-Aminophenol sulfateMeSH
Meta-aminophenolMeSH
Chemical FormulaC6H7NO
Average Molecular Weight109.13
Monoisotopic Molecular Weight109.0528
IUPAC Name3-aminophenol
Traditional Namem-aminophenol
CAS Registry Number591-27-5
SMILES
NC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2
InChI KeyCWLKGDAVCFYWJK-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
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-7900000000-6422996aedcba7475ca22014-09-20View Spectrum
Predicted GC-MSm-Aminophenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSm-Aminophenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSm-Aminophenol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSm-Aminophenol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSm-Aminophenol, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSm-Aminophenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-4900000000-a4a9fe19d8204063a0a1Spectrum
Predicted GC-MSm-Aminophenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSm-Aminophenol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSm-Aminophenol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0a4i-1900000000-721604165cf24d59220a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-014i-9000000000-bab101816aea97360a062020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-03di-1900000000-05190e4b13fe2b48bc642020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-03di-1900000000-f6c081468897bdc743a12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-03di-1900000000-d84028ec5ae86688def42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-03di-2900000000-8ddd827b9a2bd3240f6a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-03di-5900000000-8a3580af40459f7d97e92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-03xu-9400000000-75cbe10fa8b47df0df6b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-02tc-9200000000-648483fd6f1d73f805f92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-014l-9100000000-b0b9496fd6b6fbc186002020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-014i-9000000000-685317cd4c77e7cb6fa52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-014i-9000000000-16522bd5184444337e262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-014i-9000000000-c6fbe0407dca71b1bbb82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-014i-9000000000-7f1ace16286d7d01ebde2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-014r-9000000000-786f2d238803501a32b42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-014r-9000000000-8dd83d0e1c328e3936f32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-00kr-9000000000-606b4ab540d5f21542e92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-000i-9000000000-34721f503ff167afb9072020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-2900000000-9b1eee9f0d9a44187ca42020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-e51735a6e5d4a3e5eead2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-09d13b69959de03f7d242016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-6803b31dff294a8f675c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-81db2f962b909ae3bce52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-440dd43ef196996903c02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-f0a2d17e6f8da98a7b0a2016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0245818
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID11080
KEGG Compound IDC05058
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Aminophenol
METLIN IDNot Available
PubChem Compound11568
PDB IDNot Available
ChEBI ID28924
References
General References
  1. Romita P, Foti C, Mascia P, Guida S: Eyebrow allergic contact dermatitis caused by m-aminophenol and toluene-2,5-diamine secondary to a temporary black henna tattoo. Contact Dermatitis. 2018 Jul;79(1):51-52. doi: 10.1111/cod.12987. Epub 2018 Mar 25. [PubMed:29574799 ]