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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:46 UTC
HMDB IDHMDB00022
Secondary Accession Numbers
  • HMDB06022
Metabolite Identification
Common Name3-Methoxytyramine
DescriptionThe O-methylated derivative of dopamine. Dopamine is methylated by catechol-O-methyltransferase (COMT) to make 3-Methoxytyramine. This compound can be broken down to homovanillic acid by monoamine oxidase and aldehyde dehydrogenase. Elevated concentrations of this compound are indicated for a variety of brain and carcinoid tumors as well as certain mental disorders.
Structure
Thumb
Synonyms
  1. 3-Methoxy-4-hydroxyphenylethyl amine
  2. 3-Methoxytyramine
  3. 3-O-Methyldopamine
  4. 4-(2-Amino-ethyl)-2-methoxy-phenol
  5. 4-(2-Aminoethyl)-2-methoxy-Phenol
  6. 4-(2-Aminoethyl)-2-methoxyphenol
  7. 5-(2-Aminoethyl)guaiacol
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name4-(2-aminoethyl)-2-methoxyphenol
Traditional IUPAC NameO-methyldopamine
CAS Registry Number554-52-9
SMILES
COC1=C(O)C=CC(CCN)=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
InChI KeyDIVQKHQLANKJQO-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassBenzenediols
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Methoxyphenols and Derivatives
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Phenethylamine
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentCatecholamines and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.08SANGSTER (1994)
Predicted Properties
PropertyValueSource
water solubility5.36 g/LALOGPS
logP-0.04ALOGPS
logP0.53ChemAxon
logS-1.5ALOGPS
pKa (strongest acidic)10.39ChemAxon
pKa (strongest basic)9.64ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area55.48ChemAxon
rotatable bond count3ChemAxon
refractivity47.73ChemAxon
polarizability18.21ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Most Tissues
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006map00350
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0025 (0.0016-0.0029) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00377 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0014 +/- 0.0002 uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.014 (0.0052-0.028) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0005 +/- 0.0003 uMAdult (>18 years old)Not SpecifiedParkinson's Disease details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. Loeffler DA, LeWitt PA, DeMaggio AJ, Juneau PL, Milbury PE, Matson WR: Markers of dopamine depletion and compensatory response in striatum and cerebrospinal fluid. J Neural Transm Park Dis Dement Sect. 1995;9(1):45-53. Pubmed: 7605589
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021876
KNApSAcK IDNot Available
Chemspider ID1606
KEGG Compound IDC05587
BioCyc IDNot Available
BiGG ID46076
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00022
Metagene LinkHMDB00022
METLIN ID5094
PubChem Compound1669
PDB IDNot Available
ChEBI ID742324
References
Synthesis ReferenceKametani, Tetsuji; Takano, Seiichi; Karibe, Etsuo. Syntheses of heterocyclic compounds. LXXXVII. Simplified synthesis of 3-methoxy-4-hydroxy- and 3-methoxy-4-tosyloxyphenethylamine. Yakugaku Zasshi (1963), 83(11), 1035-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Leysen JE, Wynants J, Eens A, Janssen PA: Ketanserin reduces a particular monoamine pool in peripheral tissues. Mol Pharmacol. 1989 Mar;35(3):375-80. Pubmed: 2927387
  2. Faraj BA, Lawson DH, Nixon DW, Murray DR, Camp VM, Ali FM, Black M, Stacciarini W, Tarcan Y: Melanoma detection by enzyme-radioimmunoassay of L-dopa, dopamine, and 3-O-methyldopamine in urine. Clin Chem. 1981 Jan;27(1):108-12. Pubmed: 7004664
  3. Muskiet FA, Thomasson CG, Gerding AM, Fremouw-Ottevangers DC, Nagel GT, Wolthers BG: Determination of catecholamines and their 3-O-methylated metabolites in urine by mass fragmentography with use of deuterated internal standards. Clin Chem. 1979 Mar;25(3):453-60. Pubmed: 262188
  4. Sparks DL, Hunsaker JC 3rd, Slevin JT: Postmortem accumulation of 3-methoxytyramine in the brain. N Engl J Med. 1984 Aug 23;311(8):540. Pubmed: 6749220
  5. Peterson ZD, Collins DC, Bowerbank CR, Lee ML, Graves SW: Determination of catecholamines and metanephrines in urine by capillary electrophoresis-electrospray ionization-time-of-flight mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 5;776(2):221-9. Pubmed: 12138004
  6. Beck O, Faull KF: Extractive acylation and mass spectrometric assay of 3-methoxytyramine, normetanephrine, and metanephrine in cerebrospinal fluid. Anal Biochem. 1985 Sep;149(2):492-500. Pubmed: 4073504
  7. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. Pubmed: 12649306
  8. Oeltmann T, Carson R, Shannon JR, Ketch T, Robertson D: Assessment of O-methylated catecholamine levels in plasma and urine for diagnosis of autonomic disorders. Auton Neurosci. 2004 Nov 30;116(1-2):1-10. Pubmed: 15556832
  9. Yui K, Ikemoto S, Goto K: Factors for susceptibility to episode recurrence in spontaneous recurrence of methamphetamine psychosis. Ann N Y Acad Sci. 2002 Jun;965:292-304. Pubmed: 12105105
  10. Uchikura K, Horikawa R, Tanimura T, Kabasawa Y: Determination of catecholamines by radioenzymatic assay using ion-pair liquid chromatography. J Chromatogr. 1981 Apr 10;223(1):41-50. Pubmed: 7251775
  11. Carlsson A, Lindqvist M, Kehr W: Postmortal accumulation of 3-methoxytyramine in brain. Naunyn Schmiedebergs Arch Pharmacol. 1974;284(4):365-72. Pubmed: 4281061
  12. Shoup RE, Kissinger PT: Determination of urinary normetanephrine, metanephrine, and 3-methoxytyramine by liquid chromatography, with amperometric detection. Clin Chem. 1977 Jul;23(7):1268-74. Pubmed: 872373
  13. Wester P, Puu G, Reiz S, Winblad B, Wester PO: Increased monoamine metabolite concentrations and cholinesterase activities in cerebrospinal fluid of patients with acute stroke. Acta Neurol Scand. 1987 Dec;76(6):473-9. Pubmed: 3434205
  14. Yui K, Goto K, Ikemoto S: The role of noradrenergic and dopaminergic hyperactivity in the development of spontaneous recurrence of methamphetamine psychosis and susceptibility to episode recurrence. Ann N Y Acad Sci. 2004 Oct;1025:296-306. Pubmed: 15542730
  15. Rajput AH, Fenton ME, Di Paolo T, Sitte H, Pifl C, Hornykiewicz O: Human brain dopamine metabolism in levodopa-induced dyskinesia and wearing-off. Parkinsonism Relat Disord. 2004 Jun;10(4):221-6. Pubmed: 15120096

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
3-Methoxytyramine + Water + Oxygen → Homovanillin + Hydrogen peroxide + Ammoniadetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
3-Methoxytyramine + Water + Oxygen → Homovanillin + Hydrogen peroxide + Ammoniadetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + Dopamine → S-Adenosylhomocysteine + 3-Methoxytyraminedetails