Tyramine: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
biosynthesis
Citation bot (talk | contribs)
Bots
4,911,275 edits
m [394]Add: postscript, title, year, last1, first1, journal, volume, pages, issue. Tweak: journal, title, year, first1, volume, pages, issue. | Edgar181
Line 55: Line 55:


== Physical effects and pharmacology ==
== Physical effects and pharmacology ==
Tyramine is physiologically metabolized by MAO<sub>A</sub>. In [[human]]s, if monoamine metabolism is compromised by the use of [[monoamine oxidase inhibitor]]s (MAOIs) and foods high in tyramine are ingested, a [[Hypertensive emergency|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|date=August 2009}}. Most processed cheeses do not contain high enough tyramine to cause hypertensive effects, although some aged cheeses (such as [[Stilton cheese]]) do. <ref name=>{{cite journal | author=Stahl SM, Felker A | title=Monoamine oxidase inhibitors: a modern guide to an unrequited class of antidepressants | journal=CNS SPECTRUMS | volume=13 | issue=10 | year=2008 | pages=855–870 | url = http://www.cnsspectrums.com/aspx/articledetail.aspx?articleid=1791 | id= | pmid=18955941}}</ref>
Tyramine is physiologically metabolized by MAO<sub>A</sub>. In [[human]]s, if monoamine metabolism is compromised by the use of [[monoamine oxidase inhibitor]]s (MAOIs) and foods high in tyramine are ingested, a [[Hypertensive emergency|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|date=August 2009}}. Most processed cheeses do not contain high enough tyramine to cause hypertensive effects, although some aged cheeses (such as [[Stilton cheese]]) do. <ref name=>{{cite journal | author=Stahl SM, Felker A | title=Monoamine oxidase inhibitors: a modern guide to an unrequited class of antidepressants | journal=Cns Spectrums | volume=13 | issue=10 | year=2008 | pages=855–870 | url = http://www.cnsspectrums.com/aspx/articledetail.aspx?articleid=1791 | id= | pmid=18955941}}</ref>


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.
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.
Line 65: Line 65:
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 [[Trace amine-associated receptor|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.
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 [[Trace amine-associated receptor|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.<ref>{{Citation
Dietary tyramine intake has also been associated with [[migraine]] in select populations, leading many sufferers to restrict foods high in tyramine.<ref>{{Cite journal
| last = Millichap
| last = Millichap
| first = J. Gordon
| first = J. Gordon
Line 74: Line 74:
| url = http://www.nutrition4health.org/nohanews/NNS02DietMigraineHeadaches.htm
| url = http://www.nutrition4health.org/nohanews/NNS02DietMigraineHeadaches.htm
| year = 2002
| year = 2002
| postscript = <!-- Bot inserted parameter. Either remove it; or change its value to "." for the cite to end in a ".", as necessary. -->{{inconsistent citations}}
}} {{dead link|date=July 2010}}</ref>
}} {{dead link|date=July 2010}}</ref>
Reports on the tyramine-migraine link have been both affirmed and denied. A 2007 review published in Neurological Sciences<ref>{{Citation
Reports on the tyramine-migraine link have been both affirmed and denied. A 2007 review published in Neurological Sciences<ref>{{Cite journal
| last = D'Andrea
| last = D'Andrea
| journal = Neurological Sciences
| journal = Neurological Sciences
Line 94: Line 95:
| first4 = G
| first4 = G
| last5 = Granella
| last5 = Granella
| first5 = F }}</ref>
| first5 = F
| postscript = <!-- Bot inserted parameter. Either remove it; or change its value to "." for the cite to end in a ".", as necessary. -->{{inconsistent citations}} }}</ref>
presented data showing migraine and cluster headaches are characterised by an increase
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.
of circulating neurotransmitters and neuromodulators (including tyramine, octopamine and synephrine) in the hypothalamus, amygdala and dopaminergic system.
Line 108: Line 110:


==Chemistry==
==Chemistry==
In the laboratory, tyramine can be synthesized in various ways, in particular by the decarboxylation of tyrosine.<ref>{{cite journal | author = G. Barger | journal = J. Chem. Soc. | volume = 95 | pages = 1123 | year = 1909}}</ref><ref>{{Cite journal | doi = 10.1002/hlca.192500801106}}</ref><ref>{{Cite journal | doi = 10.1021/ja01335a058}}</ref>
In the laboratory, tyramine can be synthesized in various ways, in particular by the decarboxylation of tyrosine.<ref>{{cite journal | author = G. Barger | journal = J. Chem. Soc. | volume = 95 | pages = 1123 | year = 1909}}</ref><ref>{{Cite journal | doi = 10.1002/hlca.192500801106 | title = Untersuchungen in der Phenylalanin-Reihe VI. Decarboxylierung des Tyrosins und des Leucins | year = 1925 | last1 = Waser | first1 = Ernst | journal = Helvetica Chimica Acta | volume = 8 | pages = 758}}</ref><ref>{{Cite journal | doi = 10.1021/ja01335a058 | year = 1933 | last1 = Buck | first1 = Johannes S. | journal = Journal of the American Chemical Society | volume = 55 | issue = 8 | pages = 3388}}</ref>
[[File:Tyramine synthesis.png|500px|center]]
[[File:Tyramine synthesis.png|500px|center]]


Revision as of 13:41, 3 October 2011

Tyramine
Names
IUPAC name
4-(2-aminoethyl)phenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.106 Edit this at Wikidata
KEGG
MeSH Tyramine
UNII
  • 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
  • InChI=1/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
    Key: DZGWFCGJZKJUFP-UHFFFAOYAB
  • Oc1ccc(cc1)CCN
Properties
C8H11NO
Molar mass 137.179 g/mol[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 nonpsychoactive 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.

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 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)

Chemistry

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


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.
  3. ^ Millichap, J. Gordon (Summer 2002). Noha News. XXVII: 3–6 http://www.nutrition4health.org/nohanews/NNS02DietMigraineHeadaches.htmTemplate:Inconsistent citations {{cite journal}}: Missing or empty |title= (help)CS1 maint: date and year (link) CS1 maint: postscript (link) [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 17508188Template:Inconsistent citations{{cite journal}}: CS1 maint: date and year (link) CS1 maint: postscript (link)
  5. ^ Tyrosine metabolism - Reference pathway, Kyoto Encyclopedia of Genes and Genomes (KEGG)
  6. ^ G. Barger (1909). J. Chem. Soc. 95: 1123. {{cite journal}}: Missing or empty |title= (help)
  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. {{cite journal}}: Missing or empty |title= (help)
Retrieved from "https://en.wikipedia.org/w/index.php?title=Tyramine&oldid=453697597"