Tyramine

from Wikipedia, the free encyclopedia
Structural formula
Structure of tyramine
General
Surname Tyramine
other names

4-hydroxyphenylethylamine

Molecular formula C 8 H 11 NO
Brief description

beige solid

External identifiers / databases
CAS number 51-67-2
EC number 200-115-8
ECHA InfoCard 100,000,106
PubChem 5610
ChemSpider 5408
DrugBank DB08841
Wikidata Q165930
properties
Molar mass 137.2 g mol −1
Physical state

firmly

Melting point

158-163 ° C

solubility

moderate in water (11 g l −1 at 15 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tyramine is a biogenic amine . It is formed from the amino acid tyrosine by decarboxylation .

Occurrence

Tyramine resulting from the decomposition of proteins and is often naturally accompanying substance of food to the manufacturing steps such as fermentation or fermentation include, such. B. many types of cheese , red wines , meat or chocolate . It is also an ingredient of bananas and mistletoe - in the berries of the latter even in toxic concentrations.

Medicinal effect

Tyramine acts as an indirect sympathomimetic , but is quickly broken down by monoamine oxidases , so that normally no circulatory effects can be observed after oral intake. If medication with unselective MAO inhibitors is present at the same time , ingestion in the course of the inhibition of its degradation can lead to an accumulation of tyramine with possibly pronounced circulatory effects up to a hypertensive crisis , possibly with fatal consequences. One then speaks of the so-called "cheese effect". Tyramine is a non-specific substrate for monoamine oxidases.

Furthermore, like other biogenic amines (including histamine in strawberries , in shellfish and crustaceans ; serotonin in bananas and nuts ) , tyramine can trigger a food allergy . In addition, the consumption of foods rich in tyramine and histamine can be a trigger factor for migraines . Tyramine acts as a mydriatic .

Tyramine dissolves poorly in tetrahydrofuran and moderately in water, but is readily soluble in dimethyl sulfoxide (approx. 100 g / l).

literature

Entry to tyramine. In: Römpp Online . Georg Thieme Verlag, accessed on May 26, 2014.

Individual evidence

  1. a b c Tyramine data sheet (PDF) from Carl Roth , accessed on December 14, 2010.
  2. a b Tyramine data sheet from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).