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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:17:06 UTC

HMDB ID

HMDB0004989

Secondary Accession Numbers

HMDB04989

Metabolite Identification

Common Name

m-Tyramine

Description

m-Tyramine belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. m-Tyramine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make m-tyramine a potential biomarker for the consumption of these foods. m-Tyramine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on m-Tyramine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(3-Hydroxyphenyl)ethylamine	ChEBI
3-(2-Aminoethyl)phenol	ChEBI
3-Hydroxyphenethylamine	ChEBI
3-Hydroxyphenylethylamine	ChEBI
3-Tyramine	ChEBI
m-Hydroxyphenethylamine	ChEBI
Meta-tyramine	ChEBI
Metatyramine	HMDB
3-Tyramine hydrobromide	MeSH, HMDB
3-Tyramine hydrochloride	MeSH, HMDB
m-Tyramine	MeSH

Chemical Formula

C₈H₁₁NO

Average Molecular Weight

137.179

Monoisotopic Molecular Weight

137.084063979

IUPAC Name

3-(2-aminoethyl)phenol

Traditional Name

m-tyramine

CAS Registry Number

588-05-6

SMILES

NCCC1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C8H11NO/c9-5-4-7-2-1-3-8(10)6-7/h1-3,6,10H,4-5,9H2

InChI Key

GHFGJTVYMNRGBY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
2-arylethylamine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Amine
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0004989)

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0004989)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0004989)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0004989)
Feces (PMID: 28923537)

Source

Endogenous

Endogenous (HMDB: HMDB0004989)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Hypertension (MarkerDB: MDB00000465)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	164 - 165 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.4 mg/mL at 15 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.82 g/L	ALOGPS
logP	-0.17	ALOGPS
logP	0.64	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.27 m³·mol⁻¹	ChemAxon
Polarizability	15.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	127.964	31661259
DarkChem	[M-H]-	125.229	31661259
DeepCCS	[M+H]+	128.728	30932474
DeepCCS	[M-H]-	125.191	30932474
DeepCCS	[M-2H]-	162.682	30932474
DeepCCS	[M+Na]+	137.767	30932474
AllCCS	[M+H]+	129.6	32859911
AllCCS	[M+H-H2O]+	125.0	32859911
AllCCS	[M+NH4]+	133.9	32859911
AllCCS	[M+Na]+	135.2	32859911
AllCCS	[M-H]-	128.9	32859911
AllCCS	[M+Na-2H]-	130.6	32859911
AllCCS	[M+HCOO]-	132.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
m-Tyramine	NCCC1=CC(O)=CC=C1	2360.0	Standard polar	33892256
m-Tyramine	NCCC1=CC(O)=CC=C1	1516.4	Standard non polar	33892256
m-Tyramine	NCCC1=CC(O)=CC=C1	1433.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
m-Tyramine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(CCN)=C1	1466.4	Semi standard non polar	33892256
m-Tyramine,1TMS,isomer #2	C[Si](C)(C)NCCC1=CC=CC(O)=C1	1640.1	Semi standard non polar	33892256
m-Tyramine,2TMS,isomer #1	C[Si](C)(C)NCCC1=CC=CC(O[Si](C)(C)C)=C1	1610.6	Semi standard non polar	33892256
m-Tyramine,2TMS,isomer #1	C[Si](C)(C)NCCC1=CC=CC(O[Si](C)(C)C)=C1	1650.9	Standard non polar	33892256
m-Tyramine,2TMS,isomer #1	C[Si](C)(C)NCCC1=CC=CC(O[Si](C)(C)C)=C1	1730.2	Standard polar	33892256
m-Tyramine,2TMS,isomer #2	C[Si](C)(C)N(CCC1=CC=CC(O)=C1)[Si](C)(C)C	1840.5	Semi standard non polar	33892256
m-Tyramine,2TMS,isomer #2	C[Si](C)(C)N(CCC1=CC=CC(O)=C1)[Si](C)(C)C	1876.5	Standard non polar	33892256
m-Tyramine,2TMS,isomer #2	C[Si](C)(C)N(CCC1=CC=CC(O)=C1)[Si](C)(C)C	1922.9	Standard polar	33892256
m-Tyramine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=C1	1844.7	Semi standard non polar	33892256
m-Tyramine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=C1	1828.3	Standard non polar	33892256
m-Tyramine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=C1	1732.7	Standard polar	33892256
m-Tyramine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(CCN)=C1	1704.6	Semi standard non polar	33892256
m-Tyramine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC=CC(O)=C1	1855.2	Semi standard non polar	33892256
m-Tyramine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2081.5	Semi standard non polar	33892256
m-Tyramine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2101.2	Standard non polar	33892256
m-Tyramine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2018.6	Standard polar	33892256
m-Tyramine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCC1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C	2237.5	Semi standard non polar	33892256
m-Tyramine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCC1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C	2278.8	Standard non polar	33892256
m-Tyramine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCC1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C	2088.7	Standard polar	33892256
m-Tyramine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2506.6	Semi standard non polar	33892256
m-Tyramine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2417.6	Standard non polar	33892256
m-Tyramine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2094.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - m-Tyramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9700000000-2524df02b3faf73efd51	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Tyramine GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9800000000-6cabd95c9a4e0db447d4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Tyramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 10V, Positive-QTOF	splash10-0079-0900000000-c3561d44b3cf39001019	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 20V, Positive-QTOF	splash10-00di-2900000000-bb8118ca8a5fb8d17068	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 40V, Positive-QTOF	splash10-0umi-9300000000-9e5708dd981cd7611372	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 10V, Negative-QTOF	splash10-000i-0900000000-b71daf1700720243b917	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 20V, Negative-QTOF	splash10-000i-0900000000-bcc3c69fabeaccd757c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 40V, Negative-QTOF	splash10-014l-8900000000-bfeab516e28533c7ad32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 10V, Positive-QTOF	splash10-00di-3900000000-553a205c92c0389a6c00	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 20V, Positive-QTOF	splash10-00di-4900000000-82ab7f079ab031119fb0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 40V, Positive-QTOF	splash10-0fbc-9200000000-0916ad3241c3c271e7d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 10V, Negative-QTOF	splash10-000i-0900000000-fe28cc44ee8cb00ea1f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 20V, Negative-QTOF	splash10-00kr-0900000000-35a08102bf4ee84d0300	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Tyramine 40V, Negative-QTOF	splash10-014l-9600000000-e470744697c9068bac56	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000038 +/- 0.000011 uM	Adult (>18 years old)	Not Specified	Normal	8232728	details
Urine	Detected and Quantified	0.280 (0.152-0.408) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	8255370	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00034 +/- 0.0000875 uM	Adult (>18 years old)	Both	Hypertension	8255371	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Metastatic melanoma	28923537	details

Associated Disorders and Diseases

Disease References

Hypertension
Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. [PubMed:8255371 ]
Metastatic melanoma
Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]

Associated OMIM IDs

145500 (Hypertension)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023573

KNApSAcK ID

Not Available

Chemspider ID

11008

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Meta-Tyramine

METLIN ID

7240

PubChem Compound

11492

PDB ID

Not Available

ChEBI ID

89626

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000465

Good Scents ID

Not Available

References

Synthesis Reference

Falck, B.; Hillarp, N. A.; Thieme, G.; Torp, A. Fluorescence of catecholamines and related compounds condensed with formaldehyde. Brain Research Bulletin (1982), 9(1-6), xi-xv.

Material Safety Data Sheet (MSDS)

Not Available

General References

Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. [PubMed:8255370 ]
Durden DA, Davis BA: Determination of regional distributions of phenylethylamine and meta- and para-tyramine in rat brain regions and presence in human and dog plasma by an ultra-sensitive negative chemical ion gas chromatography-mass spectrometric (NCI-GC-MS) method. Neurochem Res. 1993 Sep;18(9):995-1002. [PubMed:8232728 ]
Boulton AA, Huebert ND: Biosynthesis of some urinary trace amines in the rat and the human. Res Commun Chem Pathol Pharmacol. 1981 Nov;34(2):295-310. [PubMed:7335956 ]

Showing metabocard for m-Tyramine (HMDB0004989)

MOL for HMDB0004989 (m-Tyramine)

3D MOL for HMDB0004989 (m-Tyramine)

3D SDF for HMDB0004989 (m-Tyramine)

3D-SDF for HMDB0004989 (m-Tyramine)

PDB for HMDB0004989 (m-Tyramine)

3D PDB for HMDB0004989 (m-Tyramine)

SMILES for HMDB0004989 (m-Tyramine)

INCHI for HMDB0004989 (m-Tyramine)

Structure for HMDB0004989 (m-Tyramine)

3D Structure for HMDB0004989 (m-Tyramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra