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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:50 UTC

HMDB ID

HMDB0000022

Secondary Accession Numbers

HMDB00022
HMDB0006022
HMDB06022

Metabolite Identification

Common Name

3-Methoxytyramine

Description

3-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-Methoxytyramine.mol                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  N   UNK     0       4.668  -1.540   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.334   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.334  -1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.668  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4                                                       
CONECT   11   12    6                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

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 Weight

167.205

Monoisotopic Molecular Weight

167.094628665

IUPAC Name

4-(2-aminoethyl)-2-methoxyphenol

Traditional Name

methoxytyramine

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

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)
Cerebrospinal Fluid (CSF) (PMID: 7605589)
Cerebrospinal fluid (HMDB: HMDB0000022)

Organ

Brain (HMDB: HMDB0000022)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)

Cellular substructure

Cytoplasm (HMDB: HMDB0000022)
Extracellular (HMDB: HMDB0000022)

Tissue

All Tissues (HMDB: HMDB0000022)

Source

Endogenous

Endogenous (HMDB: HMDB0000022)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (HMDB: HMDB0000022)
Tyrosine Metabolism (HMDB: HMDB0000022)

Disease pathway

Aromatic L-Aminoacid Decarboxylase Deficiency (HMDB: HMDB0000022)
Monoamine Oxidase-A Deficiency (MAO-A) (HMDB: HMDB0000022)
Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)

Drug action pathway

Disulfiram Action Pathway (HMDB: HMDB0000022)
Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Industrial application

Pharmaceutical industry

Biomarker

Parkinson's disease (MarkerDB: MDB00000011)

Physical Properties

State

Solid

Experimental Molecular 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)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	147.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002188

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.457	31661259
DarkChem	[M-H]-	134.548	31661259
AllCCS	[M+H]+	136.963	32859911
AllCCS	[M-H]-	136.997	32859911
DeepCCS	[M+H]+	137.286	30932474
DeepCCS	[M-H]-	133.458	30932474
DeepCCS	[M-2H]-	171.002	30932474
DeepCCS	[M+Na]+	146.541	30932474
AllCCS	[M+H]+	137.0	32859911
AllCCS	[M+H-H2O]+	132.6	32859911
AllCCS	[M+NH4]+	141.0	32859911
AllCCS	[M+Na]+	142.2	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	138.2	32859911
AllCCS	[M+HCOO]-	139.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxytyramine	COC1=C(O)C=CC(CCN)=C1	2467.0	Standard polar	33892256
3-Methoxytyramine	COC1=C(O)C=CC(CCN)=C1	1657.5	Standard non polar	33892256
3-Methoxytyramine	COC1=C(O)C=CC(CCN)=C1	1568.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxytyramine,1TMS,isomer #1	COC1=CC(CCN)=CC=C1O[Si](C)(C)C	1618.6	Semi standard non polar	33892256
3-Methoxytyramine,1TMS,isomer #2	COC1=CC(CCN[Si](C)(C)C)=CC=C1O	1721.4	Semi standard non polar	33892256
3-Methoxytyramine,2TMS,isomer #1	COC1=CC(CCN[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1770.7	Semi standard non polar	33892256
3-Methoxytyramine,2TMS,isomer #1	COC1=CC(CCN[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1846.2	Standard non polar	33892256
3-Methoxytyramine,2TMS,isomer #1	COC1=CC(CCN[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2000.9	Standard polar	33892256
3-Methoxytyramine,2TMS,isomer #2	COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	1938.6	Semi standard non polar	33892256
3-Methoxytyramine,2TMS,isomer #2	COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2026.4	Standard non polar	33892256
3-Methoxytyramine,2TMS,isomer #2	COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2278.3	Standard polar	33892256
3-Methoxytyramine,3TMS,isomer #1	COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1998.6	Semi standard non polar	33892256
3-Methoxytyramine,3TMS,isomer #1	COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2003.7	Standard non polar	33892256
3-Methoxytyramine,3TMS,isomer #1	COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1980.9	Standard polar	33892256
3-Methoxytyramine,1TBDMS,isomer #1	COC1=CC(CCN)=CC=C1O[Si](C)(C)C(C)(C)C	1883.4	Semi standard non polar	33892256
3-Methoxytyramine,1TBDMS,isomer #2	COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC=C1O	1992.1	Semi standard non polar	33892256
3-Methoxytyramine,2TBDMS,isomer #1	COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2258.4	Semi standard non polar	33892256
3-Methoxytyramine,2TBDMS,isomer #1	COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2294.7	Standard non polar	33892256
3-Methoxytyramine,2TBDMS,isomer #1	COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2258.3	Standard polar	33892256
3-Methoxytyramine,2TBDMS,isomer #2	COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2372.1	Semi standard non polar	33892256
3-Methoxytyramine,2TBDMS,isomer #2	COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2431.0	Standard non polar	33892256
3-Methoxytyramine,2TBDMS,isomer #2	COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2398.2	Standard polar	33892256
3-Methoxytyramine,3TBDMS,isomer #1	COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2677.9	Semi standard non polar	33892256
3-Methoxytyramine,3TBDMS,isomer #1	COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2600.1	Standard non polar	33892256
3-Methoxytyramine,3TBDMS,isomer #1	COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2327.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Methoxytyramine GC-MS (3 TMS)	splash10-00dr-2900000000-57b1653ec21d5aed99ae	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Methoxytyramine GC-MS (Non-derivatized)	splash10-00dr-2900000000-57b1653ec21d5aed99ae	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6900000000-d04baf61f1b9c22278b3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9550000000-cf6955d311ff0f030176	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyramine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-4e9a34f44fa20fd4d805	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9200000000-78e8a8758da00cc24c66	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014l-9000000000-146285917801bb44d792	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine , negative-QTOF	splash10-00di-0900000000-74c2d306bf6eb6a07be2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine , positive-QTOF	splash10-0udi-0900000000-d1ca0694bd5e8bd36f69	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine 35V, Positive-QTOF	splash10-0udi-0900000000-eeed4de3e7f5f72519af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Positive-QTOF	splash10-0udi-1900000000-c2bf7cc0e159aec8bc9c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine 35V, Positive-QTOF	splash10-0udi-0900000000-48bfff9436f67210714a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine 6V, Positive-QTOF	splash10-0udi-1900000000-f6ed6533d3bfc4041eda	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Positive-QTOF	splash10-0006-9700000000-e166795428a247265de9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine 40V, Positive-QTOF	splash10-014l-9000000000-6f72ae33fa2456098759	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine 40V, Positive-QTOF	splash10-014l-9000000000-35e2f48ababcd5fd3868	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Positive-QTOF	splash10-0udi-1900000000-fd53e2a3964d0617e0da	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Positive-QTOF	splash10-00kf-9700000000-fdcc846a0eca87296609	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Positive-QTOF	splash10-0gb9-0900000000-cb0f2ccb662476519dde	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Positive-QTOF	splash10-0uxr-0900000000-ef5b01d09a8667741704	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 40V, Positive-QTOF	splash10-0uy1-9600000000-4ac4df62e408ef8fd47c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Negative-QTOF	splash10-014i-0900000000-2f9cbc34c2bce5dc77ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Negative-QTOF	splash10-014i-0900000000-55720e7caeb2db7b0bc1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 40V, Negative-QTOF	splash10-006x-6900000000-6902b729d46692ea6897	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Positive-QTOF	splash10-0gi0-0900000000-64fba7f95df6be1d30dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Positive-QTOF	splash10-014i-0900000000-d564daf5d8113bc09867	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 40V, Positive-QTOF	splash10-0690-9600000000-5ce880a874434cb99139	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 10V, Negative-QTOF	splash10-014i-0900000000-104aad9eca02be4778f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyramine 20V, Negative-QTOF	splash10-02t9-0900000000-5fb5b2b3ed01da825735	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Brain

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.0025 (0.0016-0.0029) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00377 uM	Not Specified	Not Specified	Normal	4073504	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0014 +/- 0.0002 uM	Adult (>18 years old)	Not Specified	Normal	7605589	details
Urine	Detected and Quantified	0.31-0.55 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	0.6 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	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	0.09 (0.07-0.14) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.29-0.54 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	0.0370-0.118 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	8503438	details
Urine	Detected and Quantified	0.0130-0.0290 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	8503438	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0005 +/- 0.0003 uM	Adult (>18 years old)	Not Specified	Parkinson's Disease	7605589	details
Urine	Detected and Quantified	0.217-0.318 umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	8503438	details
Urine	Detected and Quantified	0.0140-0.0340 umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	8503438	details

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 ]
Brunner Syndrome
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

168600 (Parkinson's disease)
300615 (Brunner Syndrome)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

742324

Food Biomarker Ontology

Not Available

VMH ID

3MOXTYR

MarkerDB ID

MDB00000011

Good Scents ID

Not Available

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)

Not Available

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 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

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 + Ammonia	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

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 + Ammonia	details

Enzyme Details

3. Catechol O-methyltransferase

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-Methoxytyramine	details

Showing metabocard for 3-Methoxytyramine (HMDB0000022)

MOL for HMDB0000022 (3-Methoxytyramine)

3D MOL for HMDB0000022 (3-Methoxytyramine)

3D SDF for HMDB0000022 (3-Methoxytyramine)

3D-SDF for HMDB0000022 (3-Methoxytyramine)

PDB for HMDB0000022 (3-Methoxytyramine)

3D PDB for HMDB0000022 (3-Methoxytyramine)

SMILES for HMDB0000022 (3-Methoxytyramine)

INCHI for HMDB0000022 (3-Methoxytyramine)

Structure for HMDB0000022 (3-Methoxytyramine)

3D Structure for HMDB0000022 (3-Methoxytyramine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions