 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 |
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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 |
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| CAS Number | |
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| 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).
- ^ Cruickshank L, Kennedy AR, Shankland N (2013). "Tautomeric and ionisation forms of dopamine and tyramine in the solid state". J. Mol. Struct. 1051: 132–136. Bibcode:2013JMoSt1051..132C. doi:10.1016/j.molstruc.2013.08.002.
- ^ SciFinder, Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2021 ACD/Labs)
- ^ a b The Merck Index, 10th Ed. (1983), p. 1405, Rahway: Merck & Co.
- ^ "tyramine | C8H11NO". PubChem. Retrieved 8 April 2017.
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