3-Methoxytyramine (CHEM003259)

Record Information
Version1.0
Creation Date2014-08-29 06:17:02 UTC
Update Date2026-04-03 01:07:17 UTC
Accession NumberCHEM003259
Identification
Common Name3-Methoxytyramine
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Ether
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
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 Mass167.205 g/mol
Monoisotopic Mass167.095 g/mol
CAS Registry Number554-52-9
IUPAC Name4-(2-aminoethyl)-2-methoxyphenol
Traditional Namemethoxytyramine
SMILESCOC1=C(O)C=CC(CCN)=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Brain
  • Most Tissues
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
Aromatic L-Aminoacid Decarboxylase DeficiencySMP00170 Not Available
Monoamine oxidase-a deficiency (MAO-A)SMP00533 Not Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 Area55.48 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
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0000022
FooDB IDFDB021876
Phenol Explorer IDNot Available
KNApSAcK IDC00042132
BiGG ID46076
BioCyc IDNot Available
METLIN ID5094
PDB IDNot Available
Wikipedia Link3-Methoxytyramine
Chemspider ID1606
ChEBI ID742324
PubChem Compound ID1669
Kegg Compound IDC05587
YMDB IDNot Available
ECMDB IDM2MDB005085
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.
MSDSLink
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. Carlsson A, Lindqvist M, Kehr W: Postmortal accumulation of 3-methoxytyramine in brain. Naunyn Schmiedebergs Arch Pharmacol. 1974;284(4):365-72.
13. 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.
14. 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.
15. 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.
16. 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.