Meta-Tyramine

meta-Tyramine, also known as m-tyramine and 3-tyramine, as well as 3-hydroxyphenethylamine, is an endogenous trace amine neuromodulator and a structural analog of phenethylamine.^[1][2][3] It is a positional isomer of para-tyramine, and similarly to it, has effects on the adrenergic and dopaminergic systems.^[4][5]

meta-Tyramine

Names
Preferred IUPAC name 3-(2-Aminoethyl)phenol
Other names m-Tyramine; 3-Tyramine; 3-Hydroxyphenethylamine; 3-Hydroxyphenylethylamine; 3-OH-PEA
Identifiers
CAS Number	588-05-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:89626
ChemSpider	11008
ECHA InfoCard	100.197.155
PubChem CID	11492
UNII	K1OA38R0EZ Y
CompTox Dashboard (EPA)	DTXSID50207522
InChI InChI=1S/C8H11NO/c9-5-4-7-2-1-3-8(10)6-7/h1-3,6,10H,4-5,9H2
SMILES Oc1cc(ccc1)CCN
Properties
Chemical formula	C8H11NO
Molar mass	137.182 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

meta-Tyramine is produced in humans via aromatic amino acid decarboxylase-mediated metabolism of meta-tyrosine.^[6] meta-Tyramine can be metabolized into dopamine via peripheral or brain CYP2D6 enzymes in humans.^[7]

See also

• para-Tyramine
• 3-Methoxytyramine
• 3-Hydroxy-N,N-dimethylphenethylamine (LSM-6)