Tyramine

Source: Wikipedia, the free encyclopedia.
Not to be confused with thyramine.

Tyramine
N-methyltyramine, octopamine
Identifiers
  • 4-(2-aminoethyl)phenol
JSmol)
Density1.103 g/cm3 predicted[2]
Melting point164.5 °C (328.1 °F) [3]
Boiling point206 °C (403 °F) at 25 mmHg; 166 °C at 2 mmHg[3]
  • Oc1ccc(cc1)CCN
  • InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2 checkY
  • Key:DZGWFCGJZKJUFP-UHFFFAOYSA-N checkY

Tyramine (/ˈtaɪrəmiːn/ TY-rə-meen) (also spelled tyramin), also known under several other names,[note 1] is a naturally occurring trace amine derived from the amino acid tyrosine.[4] Tyramine acts as a catecholamine releasing agent. Notably, it is unable to cross the blood-brain barrier, resulting in only non-psychoactive peripheral sympathomimetic effects following ingestion. A hypertensive crisis can result, however, from ingestion of tyramine-rich foods in conjunction with the use of monoamine oxidase inhibitors (MAOIs).

Occurrence

Tyramine occurs widely in

fermentation or decay
. Foods that are fermented, cured, pickled, aged, or spoiled have high amounts of tyramine. Tyramine levels go up when foods are at room temperature or go past their freshness date.

Specific foods containing considerable amounts of tyramine include:[6][7]

  • strong or aged cheeses: cheddar, Swiss, Parmesan, Stilton, Gorgonzola or blue cheeses, Camembert, feta, Muenster
  • meats that are cured, smoked, or processed, such as salami, pepperoni, dry sausages, hot dogs, bologna, bacon, corned beef, pickled or smoked fish, caviar, aged chicken livers, soups or gravies made from meat extract
  • pickled or fermented foods: sauerkraut, kimchi, tofu (especially stinky tofu), pickles, miso soup, bean curd, tempeh, sourdough breads
  • condiments: soy, shrimp, fish, miso, teriyaki, and bouillon-based sauces
  • drinks: beer (especially tap or home-brewed), vermouth, red wine, sherry, liqueurs
  • beans, vegetables, and fruits: fermented or pickled vegetables, overripe fruits
  • chocolate[8]

Scientists more and more consider tyramine in food as an aspect of safety.[9] They propose projects of regulations aimed to enact control of biogenic amines in food by various strategies, including usage of proper fermentation starters, or preventing their decarboxylase activity.[10] Some authors wrote that this has already given positive results, and tyramine content in food is now lower than it has been in the past.[11]

In plants

Mistletoe (toxic and not used by humans as a food, but historically used as a medicine).[12]

In animals

Tyramine also plays a role in animals including: In

Phormia, Papilio, Bombyx, Chilo, Heliothis, Mamestra, Agrotis, and Anopheles.[15]

Physical effects and pharmacology

Evidence for the presence of tyramine in the human brain has been confirmed by postmortem analysis.

neuromodulator was revealed by the discovery of a G protein-coupled receptor with high affinity for tyramine, called TAAR1.[17][18] The TAAR1 receptor is found in the brain, as well as peripheral tissues, including the kidneys.[19] Tyramine binds to TAAR1 as an agonist in humans.[20]

Tyramine is physiologically metabolized by

synaptic vesicles. Tyramine is considered a "false neurotransmitter
", as it enters noradrenergic nerve terminals and displaces large amounts of norepinephrine, which enters the blood stream and causes vasoconstriction.

Additionally, cocaine has been found to block blood pressure rise that is originally attributed to tyramine, which is explained by the blocking of adrenaline by cocaine from reabsorption to the brain.[27]

The first signs of this effect were discovered by a British pharmacist who noticed that his wife, who at the time was on MAOI medication, had severe headaches when eating cheese.[28] For this reason, it is still called the "cheese reaction" or "cheese crisis", although other foods can cause the same problem.[29]

Most processed cheeses do not contain enough tyramine to cause hypertensive effects, although some aged cheeses (such as Stilton) do.[30][31]

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

adrenergic crisis can occur.[medical citation needed] Although the mechanism is unclear, tyramine ingestion also triggers migraine attacks in sensitive individuals and can even lead to stroke.[32] Vasodilation, dopamine, and circulatory factors are all implicated in the migraines. Double-blind trials suggest that the effects of tyramine on migraine may be adrenergic.[33]

Research reveals a possible link between

neuromodulators (including tyramine, octopamine, and synephrine) in the hypothalamus, amygdala, and dopaminergic system. People with migraine are over-represented among those with inadequate natural monoamine oxidase, resulting in similar problems to individuals taking MAO inhibitors. Many migraine attack triggers are high in tyramine.[35]

If one has had repeated exposure to tyramine, however, there is a decreased pressor response; tyramine is degraded to octopamine, which is subsequently packaged in synaptic vesicles with norepinephrine (noradrenaline).[

adrenergic receptors.[medical citation needed
]

When using a MAO inhibitor (MAOI), an 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.[36]

Biosynthesis

Biochemically, tyramine is produced by the decarboxylation of tyrosine via the action of the enzyme tyrosine decarboxylase.[37] Tyramine can, in turn, be converted to methylated alkaloid derivatives N-methyltyramine, N,N-dimethyltyramine (hordenine), and N,N,N-trimethyltyramine (candicine).

  • Tyramine
    Tyramine
  • N-Methyltyramine
    N-Methyltyramine
  • N,N-Dimethyltyramine (hordenine)
    N,N-Dimethyltyramine (hordenine)
  • N,N,N-Trimethyltyramine (candicine)
    N,N,N-Trimethyltyramine (candicine)

In humans, tyramine is produced from tyrosine, as shown in the following diagram.

Biosynthetic pathways for catecholamines and trace amines in the human brain[23][24][25]
The image above contains clickable links
In humans, catecholamines and phenethylaminergic trace amines are derived from the amino acid L-phenylalanine.

Chemistry

In the laboratory, tyramine can be synthesized in various ways, in particular by the decarboxylation of tyrosine.[38][39][40]

Tyrosine decarboxylation

Legal status

United States

Tyramine is a Schedule I

isomers, including optical, positional, or geometric isomers, and salts of isomers, if the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation."[41]

This ban is likely the product of lawmakers overly eager to ban

meta-tyramine and phenylethanolamine, a substance found in every living human body, and other common, non-hallucinogenic substances are also illegal to buy, sell, or possess in Florida.[41] Given that tyramine occurs naturally in many foods and drinks (most commonly as a by-product of bacterial fermentation), e.g. wine, cheese, and chocolate, Florida's total ban on the substance may prove difficult to enforce.[42]

Notes

  1. ^ Synonyms and alternative names include: 4-hydroxyphenethylamine, para-tyramine, mydrial, and uteramin; the latter two names are not commonly used. The IUPAC name is 4-(2-aminoethyl)phenol.

References

  1. doi:10.1016/j.molstruc.2013.08.002
    .
  2. ^ SciFinder, Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2021 ACD/Labs)
  3. ^ a b The Merck Index, 10th Ed. (1983), p. 1405, Rahway: Merck & Co.
  4. ^ "tyramine | C8H11NO". PubChem. Retrieved 8 April 2017.
  5. ^ T. A. Smith (1977) Phytochemistry 16 9–18.
  6. ^ Hall-Flavin DK (18 December 2018). "Avoid the combination of high-tyramine foods and MAOIs". Mayo Clinic.
  7. ^ Robinson J (21 June 2020). "Tyramine-Rich Foods As A Migraine Trigger & Low Tyramine Diet". WebMD.
  8. ^ "Tyramine". pubchem.ncbi.nlm.nih.gov.
  9. PMID 33418895
    .
  10. doi:10.2903/j.efsa.2011.2393
    .
  11. PMID 21971008
    .
  12. ^ "Tyramine". American Chemical Society. 19 December 2005.
  13. S2CID 14914393
    .
  14. S2CID 2056338
    .
  15. S2CID 80723865
    .
  16. PMID 623853
    .
  17. PMID 16831861
    .
  18. S2CID 2864195
    .
  19. S2CID 178180
    .
  20. PMID 27424325
    .
  21. ^ "Trimethylamine monooxygenase (Homo sapiens)". BRENDA. Technische Universität Braunschweig. July 2016. Retrieved 18 September 2016.
  22. PMID 15922018.
    Table 5: N-containing drugs and xenobiotics oxygenated by FMO
  23. ^
    PMID 19948186
    .
  24. ^
    PMID 15860375
    .
  25. ^
    PMID 24374199
    .
  26. ^ "4-Hydroxyphenylacetaldehyde". Human Metabolome Database – Version 4.0. University of Alberta. 23 July 2019. Retrieved 8 August 2019.
  27. ProQuest 1346292101
    .
  28. PMID 19742203
    .
  29. Chelsea House Publishers. pp. 30–31. Archived from the original
    (PDF) on 14 February 2017. Retrieved 6 October 2022.
  30. S2CID 6118722
    .
  31. ^ "Tyramine-restricted Diet" (PDF). W.B. Saunders Company. 1998. Archived from the original (PDF) on 13 May 2014.
  32. ^ "Tyramine". Biochemistry. Encyclopedia Britannica. Retrieved 12 November 2021.
  33. PMID 324566
    .
  34. S2CID 1548732
    .
  35. ^ "Headache Sufferer's Diet | National Headache Foundation". National Headache Foundation. Archived from the original on 2 July 2017. Retrieved 8 April 2017.
  36. S2CID 902921
    .
  37. ^ "Tyrosine metabolism - Reference pathway". Kyoto Encyclopedia of Genes and Genomes (KEGG). Archived from the original on 26 July 2019. Retrieved 3 October 2011.
  38. doi:10.1039/ct9099501123
    .
  39. doi:10.1002/hlca.192500801106
    .
  40. doi:10.1021/ja01335a058
    .
  41. ^ a b "Statutes & Constitution :View Statutes : Online Sunshine". leg.state.fl.us. Retrieved 3 April 2019.
  42. PMID 26042107
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Tyramine&oldid=1215135039"