FComEx: Tyramine (PC000038)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:37 UTC

Update date

2017-01-19 02:36:10 UTC

FoodComEx ID

PC000038

FoodDB Record

FDB000433

Chemical Information

Name

Tyramine

Description

Tyramine is a monoamine compound derived from the amino acid tyrosine. It is a very strong basic compound (based on its pKa). Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish (herring), chocolate, alcoholic beverages, cheese, yogurt, soy sauce, sauerkraut, and processed meat. Tyramine in the blood or urine is often considered as a biomarker for the consumption of cheese. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more and induce migraine headaches (PMID: 27424325). The tyramine connection to hypertensive episodes was discovered by a British pharmacist whose wife was taking an monoamine oxidase inhibitors (MAOI). He noticed that every time they had a meal with cheese, she would get a severe headache (PMID: 19742203). Tyramine acts as a neurotransmitter via a G protein-coupled receptor called TA1, which has a high affinity for tyramine. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. As an indirect sympathomimetic compound, tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase, so it prolongs the actions of adrenergic transmitters. Tyramine also provokes transmitter release from adrenergic terminals.

CAS Number

51-67-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-(4-Hydroxyphenyl)ethylamine	biospider
2-(4'-Hydroxyphenyl)ethylamine	HMDB
2-(p-Hydroxyphenyl)ethylamine	db_source
4- (2-Aminoethyl)-phenol	HMDB
4-(2-Aminoethyl)-phenol	HMDB
4-(2-Aminoethyl)-phenol(thyramin)	HMDB
4-(2-Aminoethyl)phenol	HMDB
4-(2-Aminoethyl)phenol, 9CI	db_source
4-Hydroxy-b-phenylethylamine	biospider
4-hydroxy-Benzeneethanamine	biospider
4-Hydroxy-beta-phenylethylamine	biospider
4-Hydroxy-β-phenylethylamine	Generator
4-Hydroxyphenethylamine	ChEBI
4-Hydroxyphenylethylamine	biospider
a-(4-Hydroxyphenyl)-b-aminoethane	biospider
AEF	biospider
alpha-(4-Hydroxyphenyl)-beta-aminoethane	biospider
Alpha.-(4-hydroxyphenyl)-beta-aminoethane	HMDB
b-(4-Hydroxyphenyl)ethylamine	biospider
beta-(4-Hydroxyphenyl)ethylamine	biospider
Beta-hydroxyphenylethylamine	biospider
L-tyramine	biospider
p-(2-aminoethyl)-Phenol	biospider
p-(2-Aminoethyl)phenol	biospider
P-beta-aminoethylphenol	biospider
P-hydroxy-b-phenethylamine	biospider
P-hydroxy-b-phenylethylamine	biospider
P-hydroxy-beta-phenethylamine	biospider
P-hydroxy-beta-phenylethylamine	biospider
P-hydroxyphenethylamine	biospider
P-hydroxyphenylethylamine	biospider
P-tyramine	biospider
Para-tyramine	biospider
Systogene	biospider
Tenosin-wirkstoff	biospider
Tocosine	biospider
Tyramin	biospider
Tyramine	db_source
Tyramine base	HMDB
Tyrosamine	db_source
Uteramine	biospider
β-(4-hydroxyphenyl)ethylamine	Generator

Chemical Formula

C8H11NO

IUPAC name

4-(2-aminoethyl)phenol

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

Isomeric SMILES

NCCC1=CC=C(O)C=C1

Average Molecular Weight

137.179

Monoisotopic Molecular Weight

137.084063979

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 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	Not Available
Experimental Water Solubility	10.4 mg/mL at 15 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 164-164.5° (161°)	DFC

Foods of Origin