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Tyramine
IUPAC name 4-(2-aminoethyl)phenol
Identifiers
CAS number [51-67-2]
PubChem 5610
MeSH Tyramine
SMILES C1=CC(=CC=C1CCN)O
Properties
Molecular formula C8H11NO
Molar mass 137. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component Medical Subject Headings ( MeSH) is a huge Controlled vocabulary (or metadata system for the purpose of indexing journal articles and books A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 179 g/mol[1]
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

In organic chemistry tyramine (4-hydroxy-phenethylamine, para-tyramine, p-tyramine) is a monoamine compound derived from the amino acid tyrosine. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation Chemistry (from Egyptian kēme (chem meaning "earth") is the Science concerned with the composition structure and properties Phenethylamine, or β -phenylethylamine or 2-phenylethylamine is an Alkaloid and Monoamine. Monoamine neurotransmitters are Neurotransmitters and Neuromodulators that contain one Amino group that is connected to an aromatic ring by a A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this Tyrosine (abbreviated as Tyr or Y) or 4-hydroxyphenylalanine, is one of the 20 Amino acids that are used by cells to synthesize [1] Tyramine can cause the release of stored monoamines, such as dopamine, norepinephrine, and epinephrine. Monoamine neurotransmitters are Neurotransmitters and Neuromodulators that contain one Amino group that is connected to an aromatic ring by a

Contents

Occurrence

Tyramine occurs widely in plants and animals and is metabolized by the enzyme monoamine oxidase. Plants are living Organisms belonging to the kingdom Plantae. Enzymes are Biomolecules that catalyze ( ie increase the rates of Chemical reactions Almost all enzymes are Proteins In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Decarboxylation is any Chemical reaction in which a Carboxyl group (-COOH is split off from a compound as Carbon dioxide (CO2 Fermentation in Food processing typically refers to the conversion of Sugar to Alcohol using Yeast under Anaerobic conditions 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, eggplants, figs, red plums, raspberries, peanuts, Brazil nuts, coconuts, processed meat, yeast, and an array of Cactii. Poultry is the category of Domesticated Birds which some humans keep for the purpose of collecting their eggs, or kill for their Meat and/or Beef is the Culinary name for Meat from Bovines especially domestic Cattle (cows Pork' is the Culinary name for Meat from the domestic Pig ( Sus scrofa) often specifically the fresh meat but can be used as an all-inclusive In Food preparation curing refers to various preservation and Flavoring processes especially of Meat or Fish, by the addition of Ham is the Thigh and Rump of Pork, cut from the Haunch of a Pig or Boar. Chocolate ( pronounced or /-ˈələt/ comprises a number of raw and processed foods that are produced from the seed of the tropical Cacao tree Cheese is a Food made from Milk, usually the milk of cows, Buffalo, Goats or sheep, by coagulation. Ricotta (pronounced in Italian) is an Italian Sheep milk Whey cheese. Cottage cheese is a Cheese Curd product with a mild flavor It is drained but not pressed so some Whey remains Cream cheese is a sweet soft mild-tasting white Cheese, defined by the US Department of Agriculture as containing at least 33% Milkfat (as marketed Sour cream is a Dairy product rich in Fats obtained by fermenting a regular Cream by certain kinds of Lactic acid bacteria. Yoghurt, yogurt, yoghourt, youghurt or yogourt (see spelling below is a Shrimp paste or shrimp sauce, is a common ingredient used in Southeast Asian and Southern Chinese cuisine. Soy sauce ( US) soya sauce ( Commonwealth) shoyu ( Japan) or sillao ( Peru) is a fermented Sauce Teriyaki ( Kanji: 照 り 焼 き Hiragana: てりやき is a Cooking technique used in Japanese cuisine in which foods are Tofu, also (the Japanese Romaji spelling doufu (the Chinese Pinyin spelling often used in Chinese recipes or bean curd (the literal Tempeh, or tempe in Javanese, is made by a natural culturing and controlled fermentation process that binds Soybeans into a cake form is a traditional Japanese Soup consisting of a stock called " Dashi " into which is mixed softened Miso paste Sauerkraut ( English:, German:, Yiddish: ˈzɔi̯əʀˌkʀɔi̯t is finely shredded Cabbage that has been fermented by various Vicia faba, the broad bean, fava bean, faba bean, horse bean, field bean, tic bean is a species of Green beans ( American English) or French beans ( British English) also called squeaky beans are the unripe Fruits of any kind of Bean Bean is a common name for large plant Seeds of several genera of the family Fabaceae (formerly Leguminosae used for human food or animal The snow pea ( Pisum sativum var macrocarpon) is a Legume, more specifically a variety of Pea eaten whole in its pod while still unripe The avocado ( Persea americana) (from Nahuatl āhuacatl) also known as aguacate ( Spanish) butter pear or For the fruit see Banana. For other meanings see Banana (disambiguation. The eggplant, aubergine, or brinjal ( Solanum melongena) is a plant of the family Solanaceae (also known as the nightshades Ficus is a Genus of about 850 Species of woody Trees Shrubs Vines Epiphytes and hemi-epiphytes in the family A plum or gage is a stone fruit Tree in the genus Prunus, subgenus Prunus. The raspberry (plural raspberries) is the edible Fruit of a multitude of plant species in the subgenus Idaeobatus of the genus Rubus The peanut, or Groundnut ( Arachis hypogaea) is a species in the Legume family Fabaceae native to South America, Mexico The Brazil nut ( Bertholletia excelsa) is a South American Tree in the family Lecythidaceae, and also the name of the tree's commercially The Coconut Palm ( Cocos nucifera) is a member of the Family Arecaceae (palm family In modern English usage meat most often refers to Animal tissue used as food mostly Skeletal muscle and associated Fat, but it may also refer Yeasts are a growth form of eukaryotic Microorganisms classified in the kingdom Fungi, with about 1500 Species currently described A cactus (plural cacti) is any member of the Spine plant family Cactaceae, native to the Americas

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. Human beings, humans or man (Origin 1590–1600 L homō man OL hemō the earthly one (see Humus Monoamine oxidase inhibitors ( MAOIs) are a class of powerful antidepressant drugs prescribed for the treatment of depression. Hypertension, also referred to as high blood pressure, HTN or HPN, is a medical condition in which the Blood pressure is chronically elevated Dopamine is a Hormone and Neurotransmitter occurring in a wide variety of animals including both vertebrates and invertebrates Norepinephrine ( INN) (abbreviated norepi or NE) or noradrenaline ( BAN) (abbreviated NA or NAd) is a 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. 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

Physical effects and pharmacology

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. Blood pressure is also the title of a short story by Damon Runyan in Guys and Dolls and Other Stories The torr (symbol Torr) is a non- SI unit of Pressure defined as 1/760 of an atmosphere. 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. Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels particularly the large Arteries, Arterioles

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). Octopamine is a Biogenic amine which is closely related to Noradrenaline, and has Noradrenergic and Dopaminergic effects Therefore, after repeated tyramine exposure, these vesicles contain an increased amount of octopamine and a relatively reduced amount of norepinephrine (noradrenaline). When these vesicles are secreted upon tyramine ingestion, there is a decreased pressor response, as less norepinephrine (noradrenaline) is secreted into the synapse, and octopamine does not activate alpha or beta adrenergic receptors. Chemical synapses are specialized junctions through which Neurons signal to each other and to non-neuronal cells such as those in Muscles or Glands The adrenergic receptors (or adrenoceptors) are a class of G protein-coupled receptors that are targets of the Catecholamines Adrenergic receptors

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. See Chemical synapse for an introduction to concepts and terminology used in this article The TA1 receptor is found in the brain as well as peripheral tissues, including the kidney. The brain is the center of the Nervous system in animals All Vertebrates and the majority of Invertebrates have a brain The kidneys are complicated organs that have numerous biological roles 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. Migraine is a neurological Syndrome characterized by altered bodily experiences painful headaches and nausea [2] Reports on the tyramine-migraine link have been both affirmed and denied. A recent review article found that all past studies affirming a migraine-tyramine connection were scientifically inconclusive, and noted several studies showing no connection. Two studies validated as scientifically sound reported no connection in the population evaluated.

References

  1. ^ a b PubChem
  2. ^ Millichap, J. Gordon (Summer 2002), NOHA NEWS XXVII: 3-6, <http://www.nutrition4health.org/nohanews/NNS02DietMigraineHeadaches.htm> 


See also

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

Dictionary

tyramine

-noun

  1. (chemistry) a phenolic amine, 4-hydroxy-phenethylamine, derived from the amino acid tyrosine, found in various foodstuffs and used as a sympathomimetic agent
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