| 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 |
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| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 3-Methoxy-4-hydroxyphenylethyl amine
- 3-Methoxytyramine
- 3-O-Methyldopamine
- 4-(2-Amino-ethyl)-2-methoxy-phenol
- 4-(2-Aminoethyl)-2-methoxy-Phenol
- 4-(2-Aminoethyl)-2-methoxyphenol
- 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
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| Substituents |
- Alkyl Aryl Ether
- Anisole
- Phenethylamine
- Primary Aliphatic Amine (Alkylamine)
|
| Direct Parent |
Catecholamines and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
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| 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) |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
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| Tissue Location |
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| Pathways |
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| Normal Concentrations |
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| Blood |
Detected and Quantified |
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0.0025 (0.0016-0.0029) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00377 uM |
Not Specified |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0014 +/- 0.0002 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.6 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
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0.014 (0.0052-0.028) umol/mmol creatinine |
Children (1-13 year old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|---|
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| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0005 +/- 0.0003 uM |
Adult (>18 years old) |
Not Specified |
Parkinson's Disease |
Not Available |
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| 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
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| Associated OMIM IDs |
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| External Links |
|---|
| DrugBank 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 |
| KEGG Compound ID |
C05587 |
| BioCyc ID |
Not Available |
| BiGG ID |
46076 |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB00022 |
| Metagene Link |
HMDB00022 |
| METLIN ID |
5094 |
| PubChem Compound |
1669 |
| PDB ID |
Not Available |
| ChEBI ID |
742324 |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Carlsson A, Lindqvist M, Kehr W: Postmortal accumulation of 3-methoxytyramine in brain. Naunyn Schmiedebergs Arch Pharmacol. 1974;284(4):365-72.
Pubmed: 4281061
- 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
- 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
- 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
- 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
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