Tyramine

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Tyramine
Tyramine.svg
Tyramine-3d-CPK.png
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]
Appearance colorless solid
Density 1.20 g/cm 3[2]
Melting point 164 to 165 °C (327 to 329 °F; 437 to 438 K)[3]
Boiling point 205 to 207 °C (401 to 405 °F; 478 to 480 K) at 25 mmHg; 166 °C at 2 mmHg[3]
Solubility in water 1 g in 95 mL at 15 °C[3]
Acidity (pKa) 9.74 (OH); 10.52 (NH3+) [4]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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 releasing agent. Notably, however, it is unable to cross the blood-brain barrier, resulting in only nonpsychoactive peripheral sympathomimetic effects. A hypertensive crisis can result from ingestion of tyramine-rich foods in conjunction with monoamine oxidase inhibitors (MAOIs).

Occurrence[edit]

Tyramine occurs widely in plants[5] 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, cream and Neufchâtel cheeses), sour cream, yogurt, shrimp paste, soy sauce, soybean condiments, teriyaki sauce, tempeh, miso soup, sauerkraut, kimchi, 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[edit]

Evidence for the presence of tyramine in the human brain has been confirmed by postmortem analysis.[6] Additionally, 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 TAAR1.[7][8] The TAAR1 receptor is found in the brain, as well as peripheral tissues, including the kidneys.[9]

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 also displace stored monoamines, such as dopamine, norepinephrine and epinephrine, from pre-synaptic vesicles. 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.[10] For this reason, the crisis is still called the "cheese effect" or "cheese crisis", though other foods can cause the same problem.[11]:30–31 Most processed cheeses do not contain enough tyramine to cause hypertensive effects, although some aged cheeses (such as Stilton) do.[12][13]

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.[medical citation needed]

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)[citation needed]. 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.[medical citation needed]

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.[medical citation needed]

Research reveals a possible link between migraine and elevated levels of tyramine. A 2007 review published in Neurological Sciences[14] 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[edit]

Biochemically, tyramine is produced by the decarboxylation of tyrosine via the action of the enzyme tyrosine decarboxylase.[15] Tyramine can, in turn, be converted to methylated alkaloid derivatives N-methyltyramine, N,N-dimethyltyramine (hordenine), and N,N,N-trimethyltyramine (candicine).

Chemistry[edit]

In the laboratory, tyramine can be synthesized in various ways, in particular by the decarboxylation of tyrosine.[16][17][18]

Tyramine synthesis.png

Legal Status[edit]

United States[edit]

Tyramine is not scheduled at the federal level in the United States and is therefore legal to buy, sell, or possess.[19]

US State of Florida[edit]

Tyramine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess. [20]

See also[edit]

References[edit]

  1. ^ a b PubChem
  2. ^ A. M. Andersen (1977). "The crystal and molecular structure of tyramine hydrochloride." Acta Chem. Scandinavica B 31 162-166.
  3. ^ a b c The Merck Index, 10th Ed. (1983), p.1405, Rahway: Merck & Co.
  4. ^ Kappe, T. (1965). Journal of Medicinal Chemistry 8: 368–374. doi:10.1021/jm00327a018 
  5. ^ T. A. Smith (1977) Phytochem. 16 9-18.
  6. ^ Philips, Rozdilsky, Boulton (Feb 1978). "Evidence for the presence of m-tyramine, p-tyramine, tryptamine, and phenylethylamine in the rat brain and several areas of the human brain.". Biological Psychiatry,. 13(1) (1): 51–57. PMID 623853. 
  7. ^ Navarro, Gilmour, Lewin (July 10, 2006). "A Rapid Functional Assay for the Human Trace Amine-Associated Receptor 1 Based on the Mobilization of Internal Calcium". J Biomol Screen 11: 668–693. doi:10.1177/1087057106289891. PMID 16831861. 
  8. ^ Liberles, Buck (August 10, 2006). "A second class of chemosensory receptors in the olfactory epithelium". Nature 441 (7103): 645–650. doi:10.1038/nature05066. PMID 16878137. 
  9. ^ Xie, Westmoreland, Miller (May 2008). "Modulation of monoamine transporters by common biogenic amines via trace amine-associated receptor 1 and monoamine autoreceptors in human embryonic kidney 293 cells and brain synaptosomes.". J. Pharm. 441: 629–640. doi:10.1124/jpet.107.135079. PMID 18310473. 
  10. ^ Sathyanarayana Rao TS and Vikram K. Yeragani VK (2009) Hypertensive crisis and cheese Indian J Psychiatry. 51(1): 65–66.
  11. ^ E. Siobhan Mitchell Antidepressants, chapter in Drugs, the Straight Facts, edited by David J. Triggle. 2004, Chelsea House Publishers
  12. ^ 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. 
  13. ^ Tyramine-restricted Diet 1998, W.B. Saunders Company.
  14. ^ 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 
  15. ^ Tyrosine metabolism - Reference pathway, Kyoto Encyclopedia of Genes and Genomes (KEGG)
  16. ^ G. Barger (1909). J. Chem. Soc. 95: 1123. 
  17. ^ 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. 
  18. ^ Buck, Johannes S. (1933). Journal of the American Chemical Society 55 (8): 3388. doi:10.1021/ja01335a058. 
  19. ^ §1308.11 Schedule I.
  20. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL