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Record Information
Version3.6
Creation Date2013-07-04 18:58:14 UTC
Update Date2017-03-02 22:05:23 UTC
HMDB IDHMDB60767
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
4-HydroxymethamphetamineMeSH
Pholedrin-longo-isisMeSH
Pholedrin liquidumMeSH
Pholedrine sulfate (1:1)MeSH
Pholedrine, sulfate (1:1), (+-)-isomerMeSH
Pholedrine, sulfate (2:1), (+-)-isomerMeSH
VeritolMeSH
4-Hydroxy-N-methylamphetamineMeSH
P-HydroxymethamphetamineMeSH
Pholedrine sulfate (2:1)MeSH
PulsotylMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
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
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
Water Solubility1.44 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.46 m3·mol-1ChemAxon
Polarizability19.15 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00735
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60767
      Metagene LinkHMDB60767
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available