Tyramine

Tyramine
Clinical data


ATC code	none
Pharmacokinetic data
Metabolism	CYP2D6, FMO3, MAO-A, MAO-B, PNMT, DBH, others
Metabolites	4-hydroxyphenylacetaldehyde, dopamine, N-methyltyramine, octopamine
Identifiers
IUPAC name 4-(2-aminoethyl)phenol
CAS Number	51-67-2^Y
PubChem CID	5610
IUPHAR/BPS	2150
ChemSpider	5408^Y
UNII	X8ZC7V0OX3
KEGG	C00483^Y
ChEBI	CHEBI:15760^Y
ChEMBL	CHEMBL11608^Y
ECHA InfoCard	100.000.106
Chemical and physical data
Formula	C₈H₁₁NO
Molar mass	137.179
3D model (Jmol)	Interactive image
Melting point	164.5 °C (328.1 °F)
Boiling point	206 °C (403 °F) at 25 mmHg; 166 °C at 2 mmHg
SMILES Oc1ccc(cc1)CCN
InChI InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2^Y Key:DZGWFCGJZKJUFP-UHFFFAOYSA-N^Y

Tyramine (also spelled tyramin) (/ˈtaɪrəmin/ TY-rə-meen), also known by several other names, is a naturally occurring trace amine derived from the amino acid tyrosine. 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 monoamine oxidase inhibitors (MAOIs).

Tyramine occurs widely in plants and animals, and is metabolized by various enzymes, including monoamine oxidases. In foods, it often is 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). Other foods containing considerable amounts of tyramine are 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, edamame, avocados, bananas, pineapple, eggplants, figs, red plums, raspberries, peanuts, Brazil nuts, coconuts, processed meat, yeast, an array of cacti and the holiday plant mistletoe.