Tyramine
|
Identifiers
CAS number : 51-67-2
PubChem : 5610
MeSH Tyramine : C1=CC(=CC=C1CCN)O
Molecular formula : C8H11NO
Molar Weight : 137.179 g/mol |
Tyramineis a naturally-occurring
monoamine compound and trace amine derived from the amino acid
tyrosine.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
ingested unintentionally from certain foods in conjunction with a
monoamine oxidase inhibitor (MAOI), tyramine is responsible for the
so-called "cheese effect" often 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), 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, Chinese (snow) pea pods, avocados, bananas, pineapple,
eggplants, figs, red plums, raspberries, peanuts, Brazil nuts, coconuts,
processed meat, yeast, and an array of cacti.
Metabolism
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,
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 syndrome," even though other foods can cause the same
problem.
Foods containing tyramine
This is a list of foods containing tyramine. Tyramine is an amine which
causes elevated blood pressure and tachycardia by displacing
norepinephrine from storage vesicles. Tyramine is generally produced by
decarboxylation of the amino acid tyrosine during fermentation of food
products. All protein-rich foods which have been matured will contain
more tyramine depending on the temperature and how long they have been
stored. Properly refrigerated foods will not be affected.
The amount required to cause a 30 mmHg (4.0 kPa) increase in systolic
blood pressure is referred to as TYR30, and generally averages around
500 mg in an unmedicated, healthy individual. A class of antidepressants
called MAOIs (monoamine oxidase inhibitors), and particularly MAOIs that
inhibit the isozyme MAO-A, can increase the sensitivity to tyramine if
taken orally. If sufficient quantities of tyramine are ingested after
MAO-A inhibition, hypertensive crises may occur, potentially causing
stroke or cardiac arrhythmia. There is significant evidence that
tyramine may trigger migraines in sensitive individuals.
This list is for informational purposes only; it is neither
all-inclusive nor does it go into any particular depth. If you plan to
avoid tyramine in your diet, you are urged to seek professional
guidance. Note that the exact increase in sensitivity will depend on the
MAOI used, and its dose.
* 1 Cheeses
* 2 Fruit
* 3 Processed foods
* 4 Meat and fish
* 5 Soy
* 6 Nuts and chocolate
Tyramine is a vaso-active amino acid found in foods. It precipitates
headaches in some sufferers. It is an intermediate product in the
conversion of tyrosine (an amino acid present in many proteins) to
epinephrine (an active hormone produced by the inner portion of the
adrenal gland).
Foods that contain tyramine may trigger headaches in migraineurs by
facilitating a chain reaction which results in selective cerebral
vasoconstriction followed by rebound dilation of the cranial vessels
(the most common cause of the throbbing headache pain). This sequence of
events is implicated in migraine headache.
Some of the foods containing tyramine are aged cheese, nuts, herring,
and chicken livers. A more complete diet listing is available to members
of the Foundation. Foods with high concentration of tyramine are
contraindicated with MAO1-type antidepressants.
Antidepressant tyramine
Tyramine is know to interact with monoamine oxidase inhibitors leading
to dangerous effects. Tyramine is also thought to trigger cluster
headaches. Tyramine is ordinarily harmless. But for people taking MAO
inhibitor drugs such as the antidepressant medications Nardil and
Parnate, it poses a severe threat. When combined with these drugs, it
can cause a sudden, dangerous spike in blood pressure.
Note:
These API/ chemicals are designated as
those that are used in the manufacture of the controlled substances and
are important to the manufacture of the substances. For any (Control
Substance) products Import and Export *** subjected to your country
government laws /control substance ACT.
Note /Government Notification:
N/A
|
|