ContaminantDB: 3-Methoxytyramine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:17:02 UTC

Update Date

2026-04-03 01:07:17 UTC

Accession Number

CHEM003259

Identification

Common Name

3-Methoxytyramine

Class

Small 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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

Chemical Formula

C₉H₁₃NO₂

Average Molecular Mass

167.205 g/mol

Monoisotopic Mass

167.095 g/mol

CAS Registry Number

554-52-9

IUPAC Name

Not Available

Traditional Name

methoxytyramine

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

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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:1582 )
methoxybenzene (CHEBI:1582 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Brain
Most Tissues

Pathways

Name	SMPDB Link	KEGG Link
Tyrosine Metabolism	SMP00006	map00350
Aromatic L-Aminoacid Decarboxylase Deficiency	SMP00170	Not Available
Monoamine oxidase-a deficiency (MAO-A)	SMP00533	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.36 g/L	ALOGPS
logP	-0.04	ALOGPS
logP	0.53	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10.39	ChemAxon
pKa (Strongest Basic)	9.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.48 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.73 m³·mol⁻¹	ChemAxon
Polarizability	18.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	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
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0udi-0900000000-eeed4de3e7f5f72519af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-c2bf7cc0e159aec8bc9c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0udi-0900000000-48bfff9436f67210714a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-1900000000-f6ed6533d3bfc4041eda	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9700000000-e166795428a247265de9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-6f72ae33fa2456098759	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-35e2f48ababcd5fd3868	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-fd53e2a3964d0617e0da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9700000000-fdcc846a0eca87296609	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gi0-0900000000-64fba7f95df6be1d30dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-d564daf5d8113bc09867	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0690-9600000000-5ce880a874434cb99139	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-104aad9eca02be4778f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-0900000000-5fb5b2b3ed01da825735	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000022

FooDB ID

FDB021876

Phenol Explorer ID

Not Available

KNApSAcK ID

C00042132

BiGG ID

46076

BioCyc ID

Not Available

METLIN ID

5094

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

M2MDB005085

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.

MSDS

Link

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.