Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:58:14 UTC
Update Date2023-02-21 17:30:14 UTC
HMDB IDHMDB0060767
Secondary Accession Numbers
  • HMDB60767
Metabolite Identification
Common Name4-Hydroxymethamphetamine
Description4-Hydroxymethamphetamine 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?1677000614
Synonyms
ValueSource
4-HydroxymethamphetamineMeSH
Pholedrin-longo-isisMeSH, HMDB
Pholedrin liquidumMeSH, HMDB
Pholedrine sulfate (1:1)MeSH, HMDB
Pholedrine, sulfate (1:1), (+-)-isomerMeSH, HMDB
Pholedrine, sulfate (2:1), (+-)-isomerMeSH, HMDB
VeritolMeSH, HMDB
4-Hydroxy-N-methylamphetamineMeSH, HMDB
P-HydroxymethamphetamineMeSH, HMDB
Pholedrine sulfate (2:1)MeSH, HMDB
PulsotylMeSH, HMDB
Chemical FormulaC10H15NO
Average Molecular Weight165.2322
Monoisotopic Molecular Weight165.115364107
IUPAC Name4-[2-(methylamino)propyl]phenol
Traditional Namepholedrine sulfate
CAS Registry NumberNot Available
SMILES
CNC(C)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C10H15NO/c1-8(11-2)7-9-3-5-10(12)6-4-9/h3-6,8,11-12H,7H2,1-2H3
InChI KeySBUQZKJEOOQSBV-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
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP1.12ALOGPS
logP1.33ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.86ChemAxon
pKa (Strongest Basic)10.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.46 m³·mol⁻¹ChemAxon
Polarizability19.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.48831661259
DarkChem[M-H]-136.94231661259
DeepCCS[M+H]+140.8930932474
DeepCCS[M-H]-137.06230932474
DeepCCS[M-2H]-174.75530932474
DeepCCS[M+Na]+150.29330932474
AllCCS[M+H]+137.532859911
AllCCS[M+H-H2O]+133.232859911
AllCCS[M+NH4]+141.632859911
AllCCS[M+Na]+142.832859911
AllCCS[M-H]-139.832859911
AllCCS[M+Na-2H]-141.132859911
AllCCS[M+HCOO]-142.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxymethamphetamineCNC(C)CC1=CC=C(O)C=C12440.3Standard polar33892256
4-HydroxymethamphetamineCNC(C)CC1=CC=C(O)C=C11489.5Standard non polar33892256
4-HydroxymethamphetamineCNC(C)CC1=CC=C(O)C=C11523.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxymethamphetamine,1TMS,isomer #1CNC(C)CC1=CC=C(O[Si](C)(C)C)C=C11524.8Semi standard non polar33892256
4-Hydroxymethamphetamine,1TMS,isomer #2CC(CC1=CC=C(O)C=C1)N(C)[Si](C)(C)C1686.2Semi standard non polar33892256
4-Hydroxymethamphetamine,2TMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)[Si](C)(C)C1728.6Semi standard non polar33892256
4-Hydroxymethamphetamine,2TMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)[Si](C)(C)C1695.5Standard non polar33892256
4-Hydroxymethamphetamine,2TMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)[Si](C)(C)C1767.8Standard polar33892256
4-Hydroxymethamphetamine,1TBDMS,isomer #1CNC(C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11783.0Semi standard non polar33892256
4-Hydroxymethamphetamine,1TBDMS,isomer #2CC(CC1=CC=C(O)C=C1)N(C)[Si](C)(C)C(C)(C)C1911.9Semi standard non polar33892256
4-Hydroxymethamphetamine,2TBDMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)[Si](C)(C)C(C)(C)C2223.0Semi standard non polar33892256
4-Hydroxymethamphetamine,2TBDMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)[Si](C)(C)C(C)(C)C2159.4Standard non polar33892256
4-Hydroxymethamphetamine,2TBDMS,isomer #1CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)[Si](C)(C)C(C)(C)C2052.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-aa543cec4c62e49e3a102017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9220000000-88f9572807ab2592aec32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxymethamphetamine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 10V, Positive-QTOFsplash10-014i-0900000000-12d562392b32df6e6d472017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 20V, Positive-QTOFsplash10-014r-2900000000-1ba90d221eae21d719312017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 40V, Positive-QTOFsplash10-0aor-9400000000-03e2b554733bbe0d58d72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 10V, Negative-QTOFsplash10-03di-0900000000-56e2c9c0b6c095935e832017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 20V, Negative-QTOFsplash10-03di-0900000000-2a9fa588ebc52ed933752017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 40V, Negative-QTOFsplash10-0a4i-9800000000-0d6a3777120f6f83ba522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 10V, Positive-QTOFsplash10-014i-0900000000-b87e49223bf28f5d7b512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 20V, Positive-QTOFsplash10-0a4i-4900000000-1ee2a1a917fc6ab5fc0c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 40V, Positive-QTOFsplash10-004l-9200000000-cfce27a45900b9663c4e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 10V, Negative-QTOFsplash10-03di-0900000000-5a67776f4d9f6897ce742021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 20V, Negative-QTOFsplash10-03e9-0900000000-e799217bdcf4792f91002021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxymethamphetamine 40V, Negative-QTOFsplash10-066u-6900000000-7f72cd1b15aa20abbe042021-10-12Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4494
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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