Tyramine

Tyramine
Skeletal formula of tyramine
Ball-and-stick model of the neutral (non-zwitterionic) form of tyramine found in the crystal structure[1]
Clinical data
Pronunciation/ˈtrəmn/ TY-rə-meen
Other namesTyramin; 4-Hydroxyphenethylamine; para-Tyramine; p-Tyramine; 4-Tyramine; Mydrial; Uteramin
ATC code
  • none
Pharmacokinetic data
MetabolismCYP2D6, flavin-containing monooxygenase 3, monoamine oxidase A, monoamine oxidase B, phenylethanolamine N-methyltransferase, dopamine β-hydroxylase, others
Metabolites4-Hydroxyphenylacetaldehyde, dopamine, N-methyltyramine, octopamine
Identifiers
  • 4-(2-aminoethyl)phenol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.106 Edit this at Wikidata
Chemical and physical data
FormulaC8H11NO
Molar mass137.182 g·mol−1
3D model (JSmol)
Density1.103 g/cm3 predicted[2]
Melting point164.5 °C (328.1 °F) [3]
Boiling point206 °C (403 °F) at 25 mmHg; 166 °C at 2 mmHg[3]
  • Oc1ccc(cc1)CCN
  • InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2 checkY
  • Key:DZGWFCGJZKJUFP-UHFFFAOYSA-N checkY

Tyramine (/ˈtrəmn/ 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).

  1. ^ 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.
  2. ^ SciFinder, Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2021 ACD/Labs)
  3. ^ a b The Merck Index, 10th Ed. (1983), p. 1405, Rahway: Merck & Co.
  4. ^ "tyramine | C8H11NO". PubChem. Retrieved 8 April 2017.


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