Structure via PubChem · Public domain (PubChem)
tyramine
Sign in to saveAlso known as p-tyramine, beta-(4-Hydroxyphenyl)ethylamine, p-hydroxyphenethylamine, 4-Hydroxyphenylethylamine, 4-Hydroxy-beta-phenylethylamine, p-hydroxyphenylethylamine, p-(2-Aminoethyl)phenol, 4-hydroxyphenethylamine
Tyramine ( ) (also spelled tyramin), also known under 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 the use of monoamine oxidase inhibitors (MAOIs).
Chemical data
- Formula
- C8H11NO
- Molecular weight
- 137.18 g/mol
- IUPAC name
- 4-(2-aminoethyl)phenol
- SMILES
- C1=CC(=CC=C1CCN)O
- InChIKey
- DZGWFCGJZKJUFP-UHFFFAOYSA-N
- XLogP
- 1.1
- Polar surface area
- 46.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
11,041 papers- Food sources and biomolecular targets of tyramine.Nutrition reviews · 2019
- Tyramine: from octopamine precursor to neuroactive chemical in insects.General and comparative endocrinology · 2009
- [Tyramine migraine].Revue francaise d'allergologie · 1970
- Dietary tyramine restriction for hospitalized patients on linezolid: an update.Nutrition in clinical practice : official publication of the American Society for Parenteral and Enteral Nutrition · 2010
- Tyramine in food.Lancet (London, England) · 1971
via PubMed
Wikidata facts
- Mass
- 137.084
Show 3 more facts
- chemical formula
- C₈H₁₁NO
- canonical SMILES
- C1=CC(=CC=C1CCN)O
- Commons category
- Tyramine
via Wikidata · CC0
~11 min read
Article
11 sectionsContents
- Occurrence
- In plants
- In animals
- Biological activity
- Biosynthesis
- Chemistry
- Society and culture
- Legal status
- United States
- Notes
- References
Tyramine ( ) (also spelled tyramin), also known under 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 the use of monoamine oxidase inhibitors (MAOIs).
==Occurrence== 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 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.