3-Methoxytyramine

3-Methoxytyramine

3-Methoxytyramine
Skeletal formula of 3-methoxytyramine
Ball-and-stick model of the 3-methoxytyramine molecule
Names
IUPAC name
4-(2-aminoethyl)-2-methoxyphenol
Other names
3-O-methyldopamine
Identifiers
 N
ChemSpider  N
Jmol-3D images Image
MeSH
PubChem
Properties
C9H13NO2
Molar mass 167.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: YesY/N?)

3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a metabolite of the neurotransmitter dopamine formed by the introduction of a methyl group to dopamine by the enzyme catechol-O-methyl transferase (COMT). 3-MT can be further metabolized by the enzyme monoamine oxidase (MAO) to form homovanillic acid (HVA), which is then typically excreted in the urine.

Originally thought to be physiologically inactive, 3-MT has recently been shown to act as an agonist of human TAAR1.[1]

Occurrence

3-Methoxytyramine occurs naturally in the prickly pear cactus (genus Opuntia),[2] and is in general widespread throughout the Cactaceae.[3] It has also been found in crown gall tumors on Nicotiana sp.[4]

See also

References

  1. ^
  2. ^ Retrieved on June 12, 2009 through Google Book Search.
  3. ^ T. A. Smith (1977). "Phenethylamine and related compounds in plants." Phytochem. 16 9-18.
  4. ^ S. D. Mitchell, J. L. Firmin and D. O. Gray (1984). "Enhanced 3-methoxytyramine levels in crown gall tumours and other undifferentiated plant tissues." Biochem J. 221 891-5.