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Tyramine information


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
ATC code
  • none
Pharmacokinetic data
MetabolismCYP2D6, flavin-containing monooxygenase 3, monoamine oxidase A, monoamine oxidase B, phenylethanolamine N-methyltransferase, DBH, others
Metabolites4-hydroxyphenylacetaldehyde, dopamine, N-methyltyramine, octopamine
Identifiers
IUPAC name
  • 4-(2-aminoethyl)phenol
CAS Number
  • 51-67-2 checkY
PubChem CID
  • 5610
IUPHAR/BPS
  • 2150
ChemSpider
  • 5408 checkY
UNII
  • X8ZC7V0OX3
KEGG
  • C00483 checkY
ChEBI
  • CHEBI:15760 checkY
ChEMBL
  • ChEMBL11608 checkY
CompTox Dashboard (EPA)
  • DTXSID2043874 Edit this at Wikidata
ECHA InfoCard100.000.106 Edit this at Wikidata
Chemical and physical data
FormulaC8H11NO
Molar mass137.182 g·mol−1
3D model (JSmol)
  • Interactive image
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]
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 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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neurotransmitters, and many trace amines (e.g., dopamine, norepinephrine, adrenaline, tyramine, and others) – are substituted phenethylamines. Dopamine is simply phenethylamine...

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stimulants, especially cocaine or methamphetamine, or eating foods high in tyramine while taking monoamine oxidase inhibitors. A subarachnoid hemorrhage can...

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enzyme was discovered in 1928 by Mary Bernheim in the liver and was named tyramine oxidase. The MAOs belong to the protein family of flavin-containing amine...

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Tyrosine decarboxylase

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⇌{\displaystyle \rightleftharpoons } tyramine + CO2 Hence, this enzyme has one substrate, L-tyrosine, and two products, tyramine and carbon dioxide. This enzyme...

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norepinephrine, tyramine and octopamine receptor signaling. However, due to partial overlapping in their signalling functionality tyramine and octopamine...

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include tryptamine, phenethylamine (PEA), N-methylphenethylamine, p-tyramine, m-tyramine, N-methyltyramine, p-octopamine, m-octopamine, and synephrine. These...

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blood pressure occurs when moclobemide is combined with amines such as tyramine-containing foods or pressor amine drugs, unlike with the older irreversible...

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Minor: L-Phenylalanine → L-Tyrosine → p-Tyramine → Dopamine Minor: L-Phenylalanine → m-Tyrosine → m-Tyramine → Dopamine The direct precursor of dopamine...

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substances, such as hydroxytryptamines, neurosteroids, and both m-tyramine and p-tyramine which CYP2D6 metabolizes into dopamine in the brain and liver....

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chili peppers, bell peppers, and herbs. Because of its low content of tyramine, an organic compound thought to be associated with headaches, Monterey...

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N-Methylphenethylamine (endogenous amphetamine isomer) Phenylethanolamine m-Tyramine p-Tyramine 3-Methoxytyramine N-Methyltyramine m-Octopamine p-Octopamine Synephrine...

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Synephrine

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pathway: tyrosine → tyramine → N-methyltyramine → synephrine, involving the enzymes tyrosine decarboxylase in the first step, tyramine N-methyltransferase...

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Chlorpromazine

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receptor α, intermediate for Bm tyramine receptors 1 & 2, weak for Drosophila octopamine receptor β, high for Drosophila tyramine receptor 1, intermediate for...

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Atypical depression

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C8H11NO

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