![]() Skeletal formula of tyramine | |
![]() Ball-and-stick model of the neutral (non-zwitterionic) form of tyramine found in the crystal structure[1] | |
Clinical data | |
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Pronunciation | /ˈtaɪrəmiːn/ TY-rə-meen |
Other names | Tyramin; 4-Hydroxyphenethylamine; para-Tyramine; p-Tyramine; 4-Tyramine; Mydrial; Uteramin |
ATC code |
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Pharmacokinetic data | |
Metabolism | CYP2D6, flavin-containing monooxygenase 3, monoamine oxidase A, monoamine oxidase B, phenylethanolamine N-methyltransferase, dopamine β-hydroxylase, others |
Metabolites | 4-Hydroxyphenylacetaldehyde, dopamine, N-methyltyramine, octopamine |
Identifiers | |
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CAS Number | |
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IUPHAR/BPS | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.000.106 |
Chemical and physical data | |
Formula | C8H11NO |
Molar mass | 137.182 g·mol−1 |
3D model (JSmol) | |
Density | 1.103 g/cm3 predicted[2] |
Melting point | 164.5 °C (328.1 °F) [3] |
Boiling point | 206 °C (403 °F) at 25 mmHg; 166 °C at 2 mmHg[3] |
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Tyramine (/ˈtaɪrəmiːn/ TY-rə-meen) (also spelled tyramin), also known under several other names,[note 1] is a naturally occurring trace amine derived from the amino acid tyrosine.[4] 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).
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