Human Metabolome Database Version 3.5

Showing metabocard for 3-Methoxytyramine (HMDB00022)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:46 -0700
HMDB ID HMDB00022
Secondary Accession Numbers
  • HMDB06022
Metabolite Identification
Common Name 3-Methoxytyramine
Description The 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H13NO2
Average Molecular Weight 167.205
Monoisotopic Molecular Weight 167.094628665
IUPAC Name 4-(2-aminoethyl)-2-methoxyphenol
Traditional IUPAC Name O-methyldopamine
CAS Registry Number 554-52-9
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 Key DIVQKHQLANKJQO-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Benzenediols
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Methoxyphenols and Derivatives
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Phenethylamine
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Catecholamines and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -0.08 SANGSTER (1994)
Predicted Properties
Property Value Source
Water Solubility 5.36 g/L ALOGPS
LogP -0.04 ALOGPS
LogP 0.53 ChemAxon
LogS -1.49 ALOGPS
pKa (strongest acidic) 10.39 ChemAxon
pKa (strongest basic) 9.64 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 55.48 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 47.73 ChemAxon
Polarizability 18.21 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Most Tissues
  • Brain
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0025 (0.0016-0.0029) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.00377 uM Not Specified Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0014 +/- 0.0002 uM Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
0.6 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.014 (0.0052-0.028) umol/mmol creatinine Children (1-13 year old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0005 +/- 0.0003 uM Adult (>18 years old) Not Specified Parkinson's Disease
Associated Disorders and Diseases
Disease References
Parkinson's disease
  • 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 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB021876
      KNApSAcK ID Not Available
      Chemspider ID 1606 Link_out
      KEGG Compound ID C05587 Link_out
      BioCyc ID Not Available
      BiGG ID 46076 Link_out
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00022 Link_out
      Metagene Link HMDB00022 Link_out
      METLIN ID 5094 Link_out
      PubChem Compound 1669 Link_out
      PDB ID Not Available
      ChEBI ID 742324 Link_out
      References
      Synthesis Reference Kametani, 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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: Amine oxidase [flavin-containing] B
      Reactions:
      3-Methoxytyramine + Water + Oxygen unknown Homovanillin + Hydrogen peroxide + Ammonia details
      Gene Name: MAOB
      Uniprot ID: P27338 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Amine oxidase [flavin-containing] A
      Reactions:
      3-Methoxytyramine + Water + Oxygen unknown Homovanillin + Hydrogen peroxide + Ammonia details
      Gene Name: MAOA
      Uniprot ID: P21397 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Catechol O-methyltransferase
      Reactions:
      S-Adenosylmethionine + Dopamine unknown S-Adenosylhomocysteine + 3-Methoxytyramine details
      Gene Name: COMT
      Uniprot ID: P21964 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA