Tyramine

Tyramine
	Skeletal formula of tyramine
	Ball-and-stick model of the neutral (non-zwitterionic) form of tyramine found in the crystal structure
Clinical data
Pronunciation	/ˈtaɪrəmiːn/ TY-rə-meen
Other names	Tyramin; 4-Hydroxyphenethylamine; para-Tyramine; p-Tyramine; 4-Tyramine; Mydrial; Uteramin
ATC code	none;
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
	IUPAC name 4-(2-aminoethyl)phenol;
CAS Number	51-67-2 ;
PubChem CID	5610;
IUPHAR/BPS	2150;
ChemSpider	5408 ;
UNII	X8ZC7V0OX3;
KEGG	C00483 ;
ChEBI	CHEBI:15760 ;
ChEMBL	ChEMBL11608 ;
CompTox Dashboard (EPA)	DTXSID2043874 ;
ECHA InfoCard	100.000.106
Chemical and physical data
Formula	C8H11NO
Molar mass	137.182 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.103 g/cm3 predicted
Melting point	164.5 °C (328.1 °F)
Boiling point	206 °C (403 °F) at 25 mmHg; 166 °C at 2 mmHg
	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 ; Key:DZGWFCGJZKJUFP-UHFFFAOYSA-N ;

Tyramine (/ˈtaɪrəmiːn/ TY-rə-meen) (also spelled tyramin), also known under several other names, is a naturally occurring trace amine derived from the amino acid tyrosine. 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).