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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-11-09 23:11:37 UTC |
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HMDB ID | HMDB0000022 |
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Secondary Accession Numbers | - HMDB00022
- HMDB0006022
- HMDB06022
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Metabolite Identification |
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Common Name | 3-Methoxytyramine |
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Description | 3-Methoxytyramine, also known as 3-O-methyldopamine, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is formed by the introduction of a methyl group to dopamine by the enzyme catechol-O-methyl transferase (COMT). 3-Methoxytyramine is a very strong basic compound (based on its pKa). 3-Methoxytyramine exists in all living organisms, ranging from bacteria to humans. Within humans, 3-methoxytyramine participates in a number of enzymatic reactions. In particular, 3-methoxytyramine can be converted into homovanillin; which is mediated by the enzyme amine oxidase [flavin-containing] a. In addition, 3-methoxytyramine and pyrocatechol can be biosynthesized from dopamine and guaiacol through the action of the enzyme catechol O-methyltransferase. Originally thought to be physiologically inactive, 3-MT has recently been shown to act as an agonist of human TAAR1.3-Methoxytyramine occurs naturally in the prickly pear cactus (genus Opuntia), and is in general widespread throughout the Cactaceae. It has also been found in crown gall tumors on Nicotiana sp. 3-MT can be further metabolized by the enzyme monoamine oxidase (MAO) to form homovanillic acid (HVA), which is then typically excreted in the urine. In humans, 3-methoxytyramine is a trace amine that occurs as a metabolite of dopamine. In humans, 3-methoxytyramine is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. 3-Methoxytyramine is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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3-Methoxy-4-hydroxyphenylethyl amine | HMDB | 3-O-Methyldopamine | HMDB | 4-(2-Amino-ethyl)-2-methoxy-phenol | HMDB | 4-(2-Aminoethyl)-2-methoxy-phenol | HMDB | 4-(2-Aminoethyl)-2-methoxyphenol | HMDB | 5-(2-Aminoethyl)guaiacol | HMDB | Methoxytyramine | HMDB | 3-Methoxytyramine hydrochloride | HMDB |
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Chemical Formula | C9H13NO2 |
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Average Molecular Weight | 167.205 |
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Monoisotopic Molecular Weight | 167.094628665 |
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IUPAC Name | 4-(2-aminoethyl)-2-methoxyphenol |
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Traditional Name | methoxytyramine |
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CAS Registry Number | 554-52-9 |
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SMILES | COC1=C(O)C=CC(CCN)=C1 |
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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 |
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InChI Key | DIVQKHQLANKJQO-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | Methoxyphenols |
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Direct Parent | Methoxyphenols |
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Alternative Parents | |
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Substituents | - Methoxyphenol
- Phenethylamine
- Anisole
- Phenoxy compound
- Phenol ether
- Methoxybenzene
- 2-arylethylamine
- Aralkylamine
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Ether
- Primary amine
- Amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-00dr-2900000000-57b1653ec21d5aed99ae | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00dr-2900000000-57b1653ec21d5aed99ae | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-6900000000-d04baf61f1b9c22278b3 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00e9-9550000000-cf6955d311ff0f030176 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0900000000-4e9a34f44fa20fd4d805 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9200000000-78e8a8758da00cc24c66 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014l-9000000000-146285917801bb44d792 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-00di-0900000000-74c2d306bf6eb6a07be2 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0udi-0900000000-d1ca0694bd5e8bd36f69 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0gb9-0900000000-cb0f2ccb662476519dde | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0uxr-0900000000-ef5b01d09a8667741704 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uy1-9600000000-4ac4df62e408ef8fd47c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-2f9cbc34c2bce5dc77ad | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-55720e7caeb2db7b0bc1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-006x-6900000000-6902b729d46692ea6897 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Urine
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.0025 (0.0016-0.0029) uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.00377 uM | Not Specified | Not Specified | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.0014 +/- 0.0002 uM | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.31-0.55 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.6 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.014 (0.0052-0.028) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | Urine | Detected and Quantified | 0.29-0.54 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.0370-0.118 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.0130-0.0290 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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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 | | details | Urine | Detected and Quantified | 0.217-0.318 umol/mmol creatinine | Adult (>18 years old) | Male | Brunner Syndrome | | details | Urine | Detected and Quantified | 0.0140-0.0340 umol/mmol creatinine | Adult (>18 years old) | Male | Brunner Syndrome | | details |
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Associated Disorders and Diseases |
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Disease References | Parkinson's disease |
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- 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 ]
| Brunner Syndrome |
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- Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021876 |
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KNApSAcK ID | C00042132 |
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Chemspider ID | 1606 |
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KEGG Compound ID | C05587 |
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BioCyc ID | Not Available |
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BiGG ID | 46076 |
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Wikipedia Link | 3-Methoxytyramine |
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METLIN ID | 5094 |
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PubChem Compound | 1669 |
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PDB ID | Not Available |
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ChEBI ID | 742324 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000011 |
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References |
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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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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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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