Tyramine

Title: Tyramine
CAS Registry Number: 51-67-2
CAS Name: 4-(2-Aminoethyl)phenol
Additional Names: 4-hydroxyphenethylamine; tyrosamine; 2-p-hydroxyphenylethylamine; p-b-aminoethylphenol; a-(4-hydroxyphenyl)-b-aminoethane
Molecular Formula: C8H11NO
Molecular Weight: 137.18
Percent Composition: C 70.04%, H 8.08%, N 10.21%, O 11.66%
Literature References: Decarboxylation product of tyrosine. Found in mistletoes, putrefied animal tissue, ripe cheese, ergot. Synthesis: Barger, J. Chem. Soc. 95, 1127 (1909); Waser, Helv. Chim. Acta 8, 766 (1925); Buck, J. Am. Chem. Soc. 55, 3389 (1933). Crystal and molecular structure: A. Podder et al., Acta Crystallogr. B35, 649 (1979).
Properties: Crystals from benzene or alcohol, mp 164-165°. bp25 205-207°; bp2 166°. Alkaline reaction. One gram dissolves in 95 ml water at 15°; in 10 ml boiling alcohol. Sparingly sol in benzene, xylene.
Melting point: mp 164-165°
Boiling point: bp25 205-207°; bp2 166°
Derivative Type: Hydrochloride
CAS Registry Number: 60-19-5
Trademarks: Mydrial (Winzer)
Molecular Formula: C8H11NO.HCl
Molecular Weight: 173.64
Percent Composition: C 55.34%, H 6.97%, N 8.07%, O 9.21%, Cl 20.42%
Properties: Crystals from alcohol + ether, mp 269°. Sol in water with neutral reaction.
Melting point: mp 269°
Therap-Cat: Adrenergic.
Keywords: a-Adrenergic Agonist.
Tyrocidine Tyropanoate Sodium Tyrosinase Tyrosine Tyrothricin

Tyramine
Identifiers
CAS number 51-67-2 YesY
PubChem 5610
ChemSpider 5408 YesY
UNII X8ZC7V0OX3 YesY
KEGG C00483 YesY
MeSH Tyramine
ChEBI CHEBI:15760 N
ChEMBL CHEMBL11608 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H11NO
Molar mass 137.179 g/mol[1]
Appearance colorless solid
Density 1.20 g/cm 3[2]
Melting point 164-165°C [3]
Boiling point 205-207°C at 25 mm Hg; 166°C at 2 mm Hg [3]
Solubility in water 1 g in 95 mL at 15°C [3]
Acidity (pKa) 9.74 (OH); 10.52 (NH3+) [4]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Tyramine (4-hydroxyphenethylamine; para-tyramine, mydrial or uteramin) is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine.[1] Tyramine acts as a catecholamine releasing agent. Notably, however, it is unable to cross the blood-brain barrier, resulting in only nonpsychoactive peripheral sympathomimetic effects. A hypertensive crisis can result from ingestion of tyramine-rich foods in conjunction with monoamine oxidase inhibitors (MAOIs).