Tyramine
Structural formula | ||||||||||||||||||||||
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General | ||||||||||||||||||||||
Surname | Tyramine | |||||||||||||||||||||
other names |
4-hydroxyphenylethylamine |
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Molecular formula | C 8 H 11 NO | |||||||||||||||||||||
Brief description |
beige solid |
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External identifiers / databases | ||||||||||||||||||||||
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properties | ||||||||||||||||||||||
Molar mass | 137.2 g mol −1 | |||||||||||||||||||||
Physical state |
firmly |
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Melting point |
158-163 ° C |
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solubility |
moderate in water (11 g l −1 at 15 ° C) |
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safety instructions | ||||||||||||||||||||||
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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.