3-Methoxytyramine

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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
554-52-9 N
ChemSpider 1606 N
6642
Jmol 3D model Interactive image
MeSH 3-methoxytyramine
PubChem 1669
Properties
C9H13NO2
Molar mass 167.21 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  2. Neuwinger, Hans Dieter (1996). "Cactaceae". African ethnobotany: poisons and drugs: chemistry, pharmacology, toxicology. CRC Press. p. 271. ISBN 978-3-8261-0077-2.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles> 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.