Tyramine


Tyramine
Tyramine
Identifiers
CAS number 51-67-2 YesY
PubChem 5610
ChemSpider 5408 YesY
UNII X8ZC7V0OX3 YesY
KEGG C00483 YesY
MeSH Tyramine
ChEBI CHEBI:15760 N
ChEMBL CHEMBL11608 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H11NO
Molar mass 137.179 g/mol[1]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Tyramine (4-Hydroxyphenethylamine; para-tyramine, Mydrial or Uteramin) is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine.[1] Tyramine acts as a catecholamine (dopamine, norepinephrine (noradrenaline), epinephrine (adrenaline)) releasing agent. Notably, however, it is unable to cross the blood-brain-barrier (BBB), resulting in only non-psychoactive peripheral sympathomimetic effects. When tyramine-rich foods are ingested in conjunction with a monoamine oxidase inhibitor (MAOI), tyramine is responsible for the so-called "cheese effect" sometimes seen with their use.

Contents

Occurrence

Tyramine occurs widely in plants and animals, and 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 meats that are potentially spoiled or pickled, aged, smoked, fermented, or marinated (some fish, poultry, and beef); most pork (except cured ham); chocolate; alcoholic beverages; and fermented foods, such as most cheeses (except ricotta, cottage cheese, cream cheese and neufchatel cheese), sour cream, yogurt, shrimp paste, soy sauce, soy bean condiments, teriyaki sauce, tofu, tempeh, miso soup, sauerkraut, broad (fava) beans, green bean pods, Italian flat (Romano) beans, snow peas, avocados, bananas, pineapple, eggplants, figs, red plums, raspberries, peanuts, Brazil nuts, coconuts, processed meat, yeast, and an array of cacti.

Physical effects and pharmacology

Tyramine is physiologically metabolized by MAOA. In humans, if monoamine metabolism is compromised by the use of monoamine oxidase inhibitors (MAOIs) and foods high in tyramine are ingested, a hypertensive crisis can result, as tyramine can cause the release of stored monoamines, such as dopamine, norepinephrine and epinephrine. The first signs of this were discovered by a neurologist who noticed his wife, who at the time was on MAOI medication, had severe headaches when eating cheese. For this reason, the crisis is still called the "cheese effect", though other foods can cause the same problem.[citation needed]. Most processed cheeses do not contain high enough tyramine to cause hypertensive effects, although some aged cheeses (such as Stilton cheese) do. [2]

A large dietary intake of tyramine (or a dietary intake of tyramine while taking MAO inhibitors) can cause the tyramine pressor response, which is defined as an increase in systolic blood pressure of 30 mmHg or more. The displacement of norepinephrine (noradrenaline) from neuronal storage vesicles by acute tyramine ingestion is thought to cause the vasoconstriction and increased heart rate and blood pressure of the pressor response. In severe cases, adrenergic crisis can occur.

However, if one has had repeated exposure to tyramine, there is a decreased pressor response; tyramine is degraded to octopamine, which is subsequently packaged in synaptic vesicles with norepinephrine (noradrenaline). Therefore, after repeated tyramine exposure, these vesicles contain an increased amount of octopamine and a relatively reduced amount of norepinephrine. When these vesicles are secreted upon tyramine ingestion, there is a decreased pressor response, as less norepinephrine is secreted into the synapse, and octopamine does not activate alpha or beta adrenergic receptors.

When using a MAO inhibitor (MAOI), the intake of approximately 10 to 25 mg of tyramine is required for a severe reaction compared to 6 to 10 mg for a mild reaction.

The possibility that tyramine acts directly as a neurotransmitter was revealed by the discovery of a G protein-coupled receptor with high affinity for tyramine, called TA1. The TA1 receptor is found in the brain as well as peripheral tissues, including the kidney. The existence of a receptor with high affinity for tyramine supports the hypothesis that tyramine may also act directly to affect blood pressure regulation.

Dietary tyramine intake has also been associated with migraine in select populations, leading many sufferers to restrict foods high in tyramine.[3] Reports on the tyramine-migraine link have been both affirmed and denied. A 2007 review published in Neurological Sciences[4] presented data showing migraine and cluster headaches are characterised by an increase of circulating neurotransmitters and neuromodulators (including tyramine, octopamine and synephrine) in the hypothalamus, amygdala and dopaminergic system.

Biosynthesis

Biochemically, tyramine is produced by the decarboxylation of tyrosine via the action of the enzyme tyrosine decarboxylase.[5] Tyramine can in turn be converted to methylated alkaloid derivatives N-methyltyramine, N,N-dimethyltyramine (hordenine), and

Tyramine

  • N-Methyltyramine

  • N,N-Dimethyltyramine (hordenine)

  • N,N,N-Trimethyltyramine (candicine)

  • Chemistry

    In the laboratory, tyramine can be synthesized in various ways, in particular by the decarboxylation of tyrosine.[6][7][8]

    Tyramine synthesis.png


    See also

    References

    1. ^ a b PubChem
    2. ^ Stahl SM, Felker A (2008). "Monoamine oxidase inhibitors: a modern guide to an unrequited class of antidepressants". Cns Spectrums 13 (10): 855–870. PMID 18955941. http://www.cnsspectrums.com/aspx/articledetail.aspx?articleid=1791. 
    3. ^ Millichap, J. Gordon (Summer 2002). Noha News XXVII: 3–6. http://www.nutrition4health.org/nohanews/NNS02DietMigraineHeadaches.htm [dead link]
    4. ^ D'Andrea, G; Nordera, GP; Perini, F; Allais, G; Granella, F (May 2007). "Biochemistry of neuromodulation in primary headaches: focus on anomalies of tyrosine metabolism". Neurological Sciences 28, Supplement 2: S94–S96. doi:10.1007/s10072-007-0758-4. PMID 17508188. http://www.springerlink.com/content/p745300778x24553/ 
    5. ^ Tyrosine metabolism - Reference pathway, Kyoto Encyclopedia of Genes and Genomes (KEGG)
    6. ^ G. Barger (1909). J. Chem. Soc. 95: 1123. 
    7. ^ Waser, Ernst (1925). "Untersuchungen in der Phenylalanin-Reihe VI. Decarboxylierung des Tyrosins und des Leucins". Helvetica Chimica Acta 8: 758. doi:10.1002/hlca.192500801106. 
    8. ^ Buck, Johannes S. (1933). Journal of the American Chemical Society 55 (8): 3388. doi:10.1021/ja01335a058. 

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    Look at other dictionaries:

    • Tyramine — Structure de la tyramine Général Nom IUPAC 4 hydroxy phényléthylamine …   Wikipédia en Français

    • tyramine — [ tiramin ] n. f. • 1945; de tyr(o) , du gr. turos « fromage », et amine ♦ Biochim. Amine résultant de la décarboxylation de la tyrosine et utilisée dans le traitement de l hypertension. tyramine [tiʀamin] n. f. ÉTYM. 1945, in D. D. L.; …   Encyclopédie Universelle

    • tyramine — [tī′rə mēn΄, tī′rəmin] n. [ TYR(OSINE) + AMINE] a crystalline amine, C8H11NO, found in ergot, cheeses, mistletoe, etc., and formerly used in the treatment of hypotension …   English World dictionary

    • tyramine — tiraminas statusas T sritis chemija formulė HOC₆H₄CH₂CH₂NH₂ atitikmenys: angl. tyramine rus. тирамин ryšiai: sinonimas – 4 (2 aminoetil)fenolis …   Chemijos terminų aiškinamasis žodynas

    • tyramine — noun amino acid derived from tyrosine; has a sympathomimetic action; found in chocolate and cola drinks and ripe cheese and beer patients taking MAOIs should avoid foods containing tyramine • Hypernyms: ↑amino acid, ↑aminoalkanoic acid …   Useful english dictionary

    • tyramine — noun Etymology: International Scientific Vocabulary tyrosine + amine Date: 1910 a phenolic amine C8H11NO found in various foods and beverages (as cheese and red wine) that has a sympathomimetic action and is derived from tyrosine …   New Collegiate Dictionary

    • tyramine — /tuy reuh meen /, n. Biochem. an amine, C8H11NO, abundant in ripe cheese as a breakdown product of tyrosine by removal of the carboxyl group (COOH). * * * …   Universalium

    • tyramine — noun a phenolic amine, 4 hydroxy phenethylamine, derived from the amino acid tyrosine, found in various foodstuffs and used as a sympathomimetic agent …   Wiktionary

    • tyramine — Decarboxylated tyrosine, a sympathomimetic amine having an action in some respects resembling that of epinephrine; present in ergot, mistletoe, ripe cheese, beers, red wines, and putrefied animal matter; elevated in individuals with tyrosinemia …   Medical dictionary

    • tyramine — [ tʌɪrəmi:n] noun Biochemistry a compound in cheese and other foods which in some circumstances can cause high blood pressure. Origin early 20th cent.: from tyr(osine) + amine …   English new terms dictionary