You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2013-06-15 17:22:58 UTC
Update Date2016-02-11 08:08:55 UTC
HMDB IDHMDB60592
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Hydroxynorephedrine
Description4-Hydroxynorephedrine 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
SynonymsNot Available
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name4-[(1S,2R)-2-amino-1-hydroxypropyl]phenol
Traditional Name4-[(1S,2R)-2-amino-1-hydroxypropyl]phenol
CAS Registry NumberNot Available
SMILES
C[C@@H](N)[C@@H](O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-6(10)9(12)7-2-4-8(11)5-3-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m1/s1
InChI KeyInChIKey=JAYBQRKXEFDRER-HZGVNTEJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aralkylamine
  • Phenol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • 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 Solubility11.9 mg/mLALOGPS
logP-0.47ALOGPS
logP-0.05ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.74ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.89 m3·mol-1ChemAxon
Polarizability17.98 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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET01018
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 LinkHMDB60592
Metagene LinkHMDB60592
METLIN IDNot Available
PubChem Compound6931150
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available