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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:58:09 UTC
Update Date2021-09-14 15:02:27 UTC
HMDB IDHMDB0060765
Secondary Accession Numbers
  • HMDB60765
Metabolite Identification
Common Name4-Hydroxyamphetamine
Description4-Hydroxyamphetamine is a metabolite of methamphetamine. Methamphetamine, also known as methamfetamine, meth, N-methylamphetamine, methylamphetamine, and desoxyephedrine, is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs. Methamphetamine increases alertness, concentration, energy, and in high doses, can induce euphoria, enhance self-esteem and increase libido. (Wikipedia )
Structure
Data?1563866102
Synonyms
ValueSource
HYDROXYAMFETAMINEHMDB
Hydrobromide, hydroxyamphetamineHMDB
HydroxyamphetaminHMDB
Hydroxyamphetamine hydrobromideHMDB
NorpholedrinHMDB
OxyamphetamineHMDB
p-HydroxyamphetamineHMDB
Para hydroxyamphetamineHMDB
HydroxyphenylisopropylamineHMDB
ParedrineHMDB
p HydroxyamphetamineHMDB
Para-hydroxyamphetamineHMDB
MethyltyramineHMDB
HydroxyamphetamineHMDB
Chemical FormulaC9H13NO
Average Molecular Weight151.2056
Monoisotopic Molecular Weight151.099714043
IUPAC Name4-(2-aminopropyl)phenol
Traditional Namep-hydroxyamphetamine
CAS Registry NumberNot Available
SMILES
CC(N)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3
InChI KeyGIKNHHRFLCDOEU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.13 g/LALOGPS
logP10(0.58) g/LALOGPS
logP10(1) g/LChemAxon
logS10(-1.7) g/LALOGPS
pKa (Strongest Acidic)10.48ChemAxon
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.69 m³·mol⁻¹ChemAxon
Polarizability17.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxyamphetamineCC(N)CC1=CC=C(O)C=C12607.9Standard polar33892256
4-HydroxyamphetamineCC(N)CC1=CC=C(O)C=C11410.6Standard non polar33892256
4-HydroxyamphetamineCC(N)CC1=CC=C(O)C=C11475.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyamphetamine,1TMS,isomer #1CC(N)CC1=CC=C(O[Si](C)(C)C)C=C11500.5Semi standard non polar33892256
4-Hydroxyamphetamine,1TMS,isomer #2CC(CC1=CC=C(O)C=C1)N[Si](C)(C)C1665.3Semi standard non polar33892256
4-Hydroxyamphetamine,2TMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N[Si](C)(C)C1629.4Semi standard non polar33892256
4-Hydroxyamphetamine,2TMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N[Si](C)(C)C1629.4Standard non polar33892256
4-Hydroxyamphetamine,2TMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N[Si](C)(C)C1768.6Standard polar33892256
4-Hydroxyamphetamine,2TMS,isomer #2CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C1817.4Semi standard non polar33892256
4-Hydroxyamphetamine,2TMS,isomer #2CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C1876.1Standard non polar33892256
4-Hydroxyamphetamine,2TMS,isomer #2CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C1972.4Standard polar33892256
4-Hydroxyamphetamine,3TMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C1867.0Semi standard non polar33892256
4-Hydroxyamphetamine,3TMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C1791.0Standard non polar33892256
4-Hydroxyamphetamine,3TMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C1786.5Standard polar33892256
4-Hydroxyamphetamine,1TBDMS,isomer #1CC(N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11723.5Semi standard non polar33892256
4-Hydroxyamphetamine,1TBDMS,isomer #2CC(CC1=CC=C(O)C=C1)N[Si](C)(C)C(C)(C)C1877.3Semi standard non polar33892256
4-Hydroxyamphetamine,2TBDMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N[Si](C)(C)C(C)(C)C2127.5Semi standard non polar33892256
4-Hydroxyamphetamine,2TBDMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N[Si](C)(C)C(C)(C)C2086.7Standard non polar33892256
4-Hydroxyamphetamine,2TBDMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N[Si](C)(C)C(C)(C)C2058.7Standard polar33892256
4-Hydroxyamphetamine,2TBDMS,isomer #2CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2250.8Semi standard non polar33892256
4-Hydroxyamphetamine,2TBDMS,isomer #2CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2315.1Standard non polar33892256
4-Hydroxyamphetamine,2TBDMS,isomer #2CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2135.8Standard polar33892256
4-Hydroxyamphetamine,3TBDMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2567.9Semi standard non polar33892256
4-Hydroxyamphetamine,3TBDMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2414.1Standard non polar33892256
4-Hydroxyamphetamine,3TBDMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2132.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9800000000-be314d40e4f3eec02c642017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9520000000-27b26e501065c88f2e442017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Positive-QTOFsplash10-0udr-0900000000-ce983c3333043fa751382017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Positive-QTOFsplash10-0f79-1900000000-a25d07320a871a151c902017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Positive-QTOFsplash10-0670-8900000000-01eef85998096c783c892017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Negative-QTOFsplash10-0udi-0900000000-9127f6d37951111e3ca52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Negative-QTOFsplash10-0udi-0900000000-63b9d3f1a2d2019491a42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Negative-QTOFsplash10-001i-3900000000-82c27ad632334acd666f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Negative-QTOFsplash10-0zfr-0900000000-82f62a52cf320914dd1e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Negative-QTOFsplash10-0pb9-0900000000-a9f0104927f0505bdb7e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Negative-QTOFsplash10-0006-9400000000-c422ecbb2ca5cb2ab89d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Positive-QTOFsplash10-0f79-0900000000-1559527532c5eafbb7ee2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Positive-QTOFsplash10-0a4i-3900000000-a43fa60f8dfe5ea4df1f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Positive-QTOFsplash10-004i-9100000000-5033c3c68adccf158b052021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09352
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3525
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxyamphetamine
METLIN IDNot Available
PubChem Compound3651
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available