Milk Composition Database: Showing metabocard for Tyramine (BMDB0000306)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:28:09 UTC

Update Date

2020-05-21 16:28:47 UTC

MCDB ID

BMDB0000306

Secondary Accession Numbers

BMDB00306

Metabolite Identification

Common Name

Tyramine

Description

Tyramine, also known as para-tyramine or systogene, 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. Tyramine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Tyramine exists in all living species, ranging from bacteria to humans. Tyramine participates in a number of enzymatic reactions, within cattle. In particular, Tyramine can be biosynthesized from L-tyrosine; which is catalyzed by the enzyme aromatic-L-amino-acid decarboxylase. In addition, Tyramine can be converted into dopamine; which is mediated by the enzyme tyrosinase. In cattle, tyramine is involved in the metabolic pathway called the tyrosine metabolism pathway. Tyramine is a potentially toxic compound. Tyramine has been found to be associated with several diseases known as brunner syndrome, ulcerative colitis, crohn's disease, and eosinophilic esophagitis; also tyramine has been linked to the inborn metabolic disorders including celiac disease.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(p-Hydroxyphenyl)ethylamine	ChEBI
4-Hydroxy-beta-phenylethylamine	ChEBI
4-Hydroxyphenethylamine	ChEBI
4-Hydroxyphenylethylamine	ChEBI
beta-(4-Hydroxyphenyl)ethylamine	ChEBI
p-(2-Aminoethyl)phenol	ChEBI
p-Hydroxyphenethylamine	ChEBI
p-Hydroxyphenylethylamine	ChEBI
p-Tyramine	ChEBI
Tyramin	ChEBI
4-Hydroxy-b-phenylethylamine	Generator
4-Hydroxy-β-phenylethylamine	Generator
b-(4-Hydroxyphenyl)ethylamine	Generator
Β-(4-hydroxyphenyl)ethylamine	Generator
2-(4'-Hydroxyphenyl)ethylamine	HMDB
2-(4-Hydroxyphenyl)ethylamine	HMDB
4-(2-Aminoethyl)-phenol	HMDB
4-(2-Aminoethyl)-phenol(thyramin)	HMDB
4-(2-Aminoethyl)phenol	HMDB
4-Hydroxy-benzeneethanamine	HMDB
a-(4-Hydroxyphenyl)-b-aminoethane	HMDB
alpha-(4-Hydroxyphenyl)-beta-aminoethane	HMDB
p-(2-Aminoethyl)-phenol	HMDB
p-beta-Aminoethylphenol	HMDB
p-Hydroxy-b-phenethylamine	HMDB
p-Hydroxy-b-phenylethylamine	HMDB
p-Hydroxy-beta-phenethylamine	HMDB
p-Hydroxy-beta-phenylethylamine	HMDB
Systogene	HMDB
Tenosin-wirkstoff	HMDB
Tocosine	HMDB
Tyramine base	HMDB
Tyrosamine	HMDB
Uteramine	HMDB
Para-tyramine	HMDB
4 Hydroxyphenethylamine	HMDB
2-(4-Hydroxyphenyl)ethanamine	HMDB
2-(4’-hydroxyphenyl)ethylamine	HMDB
p-Hydroxy-β-phenylethylamine	HMDB
p-Β-aminoethylphenol	HMDB
Α-(4-hydroxyphenyl)-β-aminoethane	HMDB

Chemical Formula

C₈H₁₁NO

Average Molecular Weight

137.179

Monoisotopic Molecular Weight

137.084063979

IUPAC Name

4-(2-aminoethyl)phenol

Traditional Name

tyramine

CAS Registry Number

51-67-2

SMILES

NCCC1=CC=C(O)C=C1

InChI Identifier

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

InChI Key

DZGWFCGJZKJUFP-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-2-unsubstituted benzenoid
Aralkylamine
Phenol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monoamine molecular messenger (CHEBI:15760 )
primary amino compound (CHEBI:15760 )
tyramines (CHEBI:15760 )
Biogenic amines (C00483 )
Tyramine derivatives (C00483 )

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.14	ALOGPS
logP	0.68	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.41	ChemAxon
pKa (Strongest Basic)	9.66	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	15.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-2900000000-273503edc6a220e152b6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-2900000000-80980d19fa83d4b86f91	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9700000000-78d2ae48da1eee18358e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9200000000-50c21473a7d48011358c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-1900000000-9b1000a8978b57919c35	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-273503edc6a220e152b6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-80980d19fa83d4b86f91	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-78d2ae48da1eee18358e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-69892c95ab2778a208b3	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9600000000-1d5276a762318a00832d	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-7900000000-8f3b164f36bc5a4df4d7	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-0900000000-066947a256844eb6cbdc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-0900000000-4b0f190d7304f2cec82d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-2feedb2abf4fe5413452	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-052r-0900000000-e67940e0a4f0f1b565c4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00lr-9400000000-47a2e802a22167ed8a63	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-3229081a448a277191a2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004l-9300000000-e2fc12d41e4c40a9a296	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-92f0b12d0a64443cede8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-001i-9200000000-50c21473a7d48011358c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-d7e9a8705227b4504c5c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-3f02b334907c40a8315c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-e98b3afc6fad78d45d38	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-54239e66d89de3096ca8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0079-0902000000-f09759fc06ef461f3aa5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-9ffe6ee0ce68182216f7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-020a5decfb44fc4f97df	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0930000000-32ccc375e75dbab3195c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-51c6cc08017f1672b791	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-1900000000-55c25dd64462c06c5316	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0f96-9500000000-83a70aec6da00b51a6df	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-004i-9100000000-5f044e831c0d2db255fa	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-99edae3913507430bf9f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-8944003750ac547c2024	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-00e85becc8cfc59bdb10	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-58e8539844dcdbc977cc	2017-09-14	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-053r-9500000000-6deb2b5d214f768ca448	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 29291809	details

External Links

HMDB ID

HMDB0000306

DrugBank ID

DB08841

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

5610

PDB ID

Not Available

ChEBI ID

15760

References

Synthesis Reference

Wang, Yalou; Xie, Dongmei. Improved synthesis method of tyramine. Zhongguo Yaowu Huaxue Zazhi (1994), 4(2), 128-9.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Showing metabocard for Tyramine (BMDB0000306)

Structure for BMDB0000306 (Tyramine)