Tyramine

4-hydroxy -phenylethylamine

Beige solid

Fixed

158-163 ° C

Poorly in water ( 11 g · l-1 at 15 ° C)

Attention

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

Occurrence

Tyramine is formed in the decomposition of proteins, and is often naturally accompanying material of food, for their production include steps such as fermentation or fermentation, for example, many types of cheese, chocolate or red. It is further ingredient of bananas and mistletoe - berries in the latter even at toxic levels.

Medical effects

Tyramine acts as an indirect sympathomimetic, but is rapidly degraded by monoamine oxidases, so that, normally, when taken orally no cycle effect can be observed. In a concomitant medication with non-selective MAO inhibitors may ingestion during the inhibition of its degradation to an accumulation of tyramine with possibly very pronounced circulation effect up to hypertensive crisis, possibly with fatal consequences result. One then speaks of the so-called "cheese effect". Tyramine is a non-specific substrate of monoamine oxidases.

Furthermore, tyramine, like other biogenic amines ( histamine, inter alia, in strawberries, in shells and crustaceans; serotonin in bananas and nuts) be the trigger for a food allergy. In addition, the consumption tyramine and histamine- rich foods represent a triggering factor for migraine. Tyramine acts as a mydriatic.

Tyramine in tetrahydrofuran bad, in dimethyl sulfoxide soluble (about 100 g / l).