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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:11:37 UTC
HMDB IDHMDB0000022
Secondary Accession Numbers
  • HMDB00022
  • HMDB0006022
  • HMDB06022
Metabolite Identification
Common Name3-Methoxytyramine
Description3-methoxytyramine, also known as 4-(2-amino-Ethyl)-2-methoxy-phenol or 3-O-Methyldopamine, is classified as a member of the Methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-methoxytyramine is considered to be slightly soluble (in water) and acidic. 3-methoxytyramine can be found primarily in human brain and most tissues tissues; and in blood, cerebrospinal fluid (csf) or urine. Within a cell, 3-methoxytyramine is primarily located in the cytoplasm
Structure
Data?1582752108
Synonyms
ValueSource
3-Methoxy-4-hydroxyphenylethyl amineHMDB
3-O-MethyldopamineHMDB
4-(2-Amino-ethyl)-2-methoxy-phenolHMDB
4-(2-Aminoethyl)-2-methoxy-phenolHMDB
4-(2-Aminoethyl)-2-methoxyphenolHMDB
5-(2-Aminoethyl)guaiacolHMDB
MethoxytyramineHMDB
3-Methoxytyramine hydrochlorideHMDB
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name4-(2-aminoethyl)-2-methoxyphenol
Traditional Namemethoxytyramine
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
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.
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
  • 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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.08SANGSTER (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available147.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00002188
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.36 g/LALOGPS
logP10(-0.04) g/LALOGPS
logP10(0.53) g/LChemAxon
logS10(-1.5) g/LALOGPS
pKa (Strongest Acidic)10.39ChemAxon
pKa (Strongest Basic)9.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.73 m³·mol⁻¹ChemAxon
Polarizability18.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.45731661259
DarkChem[M-H]-134.54831661259
AllCCS[M+H]+136.96332859911
AllCCS[M-H]-136.99732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-MethoxytyramineCOC1=C(O)C=CC(CCN)=C12467.0Standard polar33892256
3-MethoxytyramineCOC1=C(O)C=CC(CCN)=C11657.5Standard non polar33892256
3-MethoxytyramineCOC1=C(O)C=CC(CCN)=C11568.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methoxytyramine,1TMS,isomer #1COC1=CC(CCN)=CC=C1O[Si](C)(C)C1618.6Semi standard non polar33892256
3-Methoxytyramine,1TMS,isomer #2COC1=CC(CCN[Si](C)(C)C)=CC=C1O1721.4Semi standard non polar33892256
3-Methoxytyramine,2TMS,isomer #1COC1=CC(CCN[Si](C)(C)C)=CC=C1O[Si](C)(C)C1770.7Semi standard non polar33892256
3-Methoxytyramine,2TMS,isomer #1COC1=CC(CCN[Si](C)(C)C)=CC=C1O[Si](C)(C)C1846.2Standard non polar33892256
3-Methoxytyramine,2TMS,isomer #1COC1=CC(CCN[Si](C)(C)C)=CC=C1O[Si](C)(C)C2000.9Standard polar33892256
3-Methoxytyramine,2TMS,isomer #2COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O1938.6Semi standard non polar33892256
3-Methoxytyramine,2TMS,isomer #2COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O2026.4Standard non polar33892256
3-Methoxytyramine,2TMS,isomer #2COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O2278.3Standard polar33892256
3-Methoxytyramine,3TMS,isomer #1COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C1998.6Semi standard non polar33892256
3-Methoxytyramine,3TMS,isomer #1COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2003.7Standard non polar33892256
3-Methoxytyramine,3TMS,isomer #1COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C1980.9Standard polar33892256
3-Methoxytyramine,1TBDMS,isomer #1COC1=CC(CCN)=CC=C1O[Si](C)(C)C(C)(C)C1883.4Semi standard non polar33892256
3-Methoxytyramine,1TBDMS,isomer #2COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC=C1O1992.1Semi standard non polar33892256
3-Methoxytyramine,2TBDMS,isomer #1COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2258.4Semi standard non polar33892256
3-Methoxytyramine,2TBDMS,isomer #1COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2294.7Standard non polar33892256
3-Methoxytyramine,2TBDMS,isomer #1COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2258.3Standard polar33892256
3-Methoxytyramine,2TBDMS,isomer #2COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2372.1Semi standard non polar33892256
3-Methoxytyramine,2TBDMS,isomer #2COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2431.0Standard non polar33892256
3-Methoxytyramine,2TBDMS,isomer #2COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2398.2Standard polar33892256
3-Methoxytyramine,3TBDMS,isomer #1COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2677.9Semi standard non polar33892256
3-Methoxytyramine,3TBDMS,isomer #1COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2600.1Standard non polar33892256
3-Methoxytyramine,3TBDMS,isomer #1COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2327.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Methoxytyramine GC-MS (3 TMS)splash10-00dr-2900000000-57b1653ec21d5aed99ae2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methoxytyramine GC-MS (Non-derivatized)splash10-00dr-2900000000-57b1653ec21d5aed99ae2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-d04baf61f1b9c22278b32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9550000000-cf6955d311ff0f0301762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0udi-0900000000-4e9a34f44fa20fd4d8052012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0006-9200000000-78e8a8758da00cc24c662012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014l-9000000000-146285917801bb44d7922012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine , negative-QTOFsplash10-00di-0900000000-74c2d306bf6eb6a07be22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine , positive-QTOFsplash10-0udi-0900000000-d1ca0694bd5e8bd36f692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine 35V, Positive-QTOFsplash10-0udi-0900000000-eeed4de3e7f5f72519af2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine 10V, Positive-QTOFsplash10-0udi-1900000000-c2bf7cc0e159aec8bc9c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine 35V, Positive-QTOFsplash10-0udi-0900000000-48bfff9436f67210714a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine 6V, Positive-QTOFsplash10-0udi-1900000000-f6ed6533d3bfc4041eda2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine 20V, Positive-QTOFsplash10-0006-9700000000-e166795428a247265de92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine 40V, Positive-QTOFsplash10-014l-9000000000-6f72ae33fa24560987592021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine 40V, Positive-QTOFsplash10-014l-9000000000-35e2f48ababcd5fd38682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine 10V, Positive-QTOFsplash10-0udi-1900000000-fd53e2a3964d0617e0da2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxytyramine 20V, Positive-QTOFsplash10-00kf-9700000000-fdcc846a0eca872966092021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Positive-QTOFsplash10-0gb9-0900000000-cb0f2ccb662476519dde2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Positive-QTOFsplash10-0uxr-0900000000-ef5b01d09a86677417042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 40V, Positive-QTOFsplash10-0uy1-9600000000-4ac4df62e408ef8fd47c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Negative-QTOFsplash10-014i-0900000000-2f9cbc34c2bce5dc77ad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Negative-QTOFsplash10-014i-0900000000-55720e7caeb2db7b0bc12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 40V, Negative-QTOFsplash10-006x-6900000000-6902b729d46692ea68972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Positive-QTOFsplash10-0gi0-0900000000-64fba7f95df6be1d30dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Positive-QTOFsplash10-014i-0900000000-d564daf5d8113bc098672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 40V, Positive-QTOFsplash10-0690-9600000000-5ce880a874434cb991392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Negative-QTOFsplash10-014i-0900000000-104aad9eca02be4778f82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Negative-QTOFsplash10-02t9-0900000000-5fb5b2b3ed01da8257352021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
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 Quantified0.31-0.55 umol/mmol creatinineAdult (>18 years old)FemaleNormal 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
UrineDetected and Quantified0.29-0.54 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0370-0.118 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0130-0.0290 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0005 +/- 0.0003 uMAdult (>18 years old)Not SpecifiedParkinson's Disease details
UrineDetected and Quantified0.217-0.318 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome details
UrineDetected and Quantified0.0140-0.0340 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome 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 ]
Brunner Syndrome
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021876
KNApSAcK IDC00042132
Chemspider ID1606
KEGG Compound IDC05587
BioCyc IDNot Available
BiGG ID46076
Wikipedia Link3-Methoxytyramine
METLIN ID5094
PubChem Compound1669
PDB IDNot Available
ChEBI ID742324
Food Biomarker OntologyNot Available
VMH ID3MOXTYR
MarkerDB IDMDB00000011
Good Scents IDNot Available
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