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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-04-06 16:20:15 UTC
Update Date2019-07-23 05:57:29 UTC
HMDB IDHMDB0012162
Secondary Accession Numbers
  • HMDB12162
Metabolite Identification
Common Name4-Methoxytyramine
Description4-Methoxytyramine is a catecholamine derivative. Catecholamines are important components of the central nervous system. A number of diseases are characterized by abnormal levels of catecholamines. For example, patients with Parkinson's disease have lower levels of dopamine than normal. L-3,4-Dihydroxyphennylalanune (L-Dopa), a catechol a-amino acid, is widely used in the treatment of Parkinson's disease. When L-Dopa is given orally to patients, the most prominent metabolite is 3-methoxy-4-hydroxyphenylalanine. However, a part of L-Dopa is methylated to 3-hydroxy-4-methylphenylalanine and to 3-hydroxy-4-methoxyphenethylamine. It has been reported that 4-O-methylation of catecholamines is implicated in some neuropsychiatric disorders and thus 3-hydroxy-4-methoxyphenethylamine appears to be the endogenous "toxin" in Parkinson's disease. Consequently, the determination of plasma levels of 3-hydroxy-4-methoxyphenethylamine is important following oral L-Dopa therapy (PMID: 6518609 ).
Structure
Data?1563861449
Synonyms
ValueSource
3-Hydroxy-4-methoxy-benzeneethanamineHMDB
3-Hydroxy-4-methoxyphenethylamineHMDB
4-(2-Aminoethyl)guaiacol hydrochlorideHMDB
4-Methoxy-3-hydroxyphenethylamine hydrochlorideHMDB
4-O-MethyldopamineHMDB
5-(2-Aminoethyl)-2-methoxyphenolHMDB
5-Hydroxy-4-methoxy-benzeneethanamineHMDB
Lopac-H-3132HMDB
3-Hydroxy-4-methoxyphenethylamine hydrochlorideMeSH
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name5-(2-aminoethyl)-2-methoxyphenol
Traditional Name5-(2-aminoethyl)-2-methoxyphenol
CAS Registry Number3213-30-7
SMILES
COC1=C(O)C=C(CCN)C=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-12-9-3-2-7(4-5-10)6-8(9)11/h2-3,6,11H,4-5,10H2,1H3
InChI KeyWJXQFVMTIGJBFX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenethylamine
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 2-arylethylamine
  • Aralkylamine
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Hydrocarbon derivative
  • Primary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.68 g/LALOGPS
logP-0.06ALOGPS
logP0.45ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)10.24ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.73 m³·mol⁻¹ChemAxon
Polarizability18.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-04f173662830730ff7b7JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9830000000-566fa08a0eace6a43306JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0900000000-cb0f2ccb662476519ddeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-249e196fc14d685f1468JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy0-9600000000-7665f4c41242de21beeeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-6a246c6614040c50b45fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-960e238c3ffc12d3e76fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-6900000000-1863ab44a6327bc1600eJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.022 +/- 0.015 uMAdult (>18 years old)Not Specified
Parkinson's disease
details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. Ishimitsu T, Hirose S, Asahara K, Imaizumi M: The formation of 3-hydroxy-4-methoxyphenylalanine and 3-hydroxy-4-methoxyphenethylamine in plasma during L-DOPA therapy in patients with Parkinson's disease. Chem Pharm Bull (Tokyo). 1984 Aug;32(8):3320-2. [PubMed:6518609 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028818
KNApSAcK IDNot Available
Chemspider ID1685
KEGG Compound IDNot Available
BioCyc IDCPD-7665
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1748
PDB IDNot Available
ChEBI ID89641
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ishimitsu T, Hirose S, Asahara K, Imaizumi M: The formation of 3-hydroxy-4-methoxyphenylalanine and 3-hydroxy-4-methoxyphenethylamine in plasma during L-DOPA therapy in patients with Parkinson's disease. Chem Pharm Bull (Tokyo). 1984 Aug;32(8):3320-2. [PubMed:6518609 ]