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
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[edit]

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[edit]

References[edit]

  1. ^ Sotnikova TD, Beaulieu JM, Espinoza S, et al. (2010). "The dopamine metabolite 3-methoxytyramine is a neuromodulator". PLOS ONE. 5 (10): e13452. doi:10.1371/journal.pone.0013452. PMC 2956650free to read. PMID 20976142. 
  2. ^ Neuwinger, Hans Dieter (1996). "Cactaceae". African ethnobotany: poisons and drugs: chemistry, pharmacology, toxicology. CRC Press. p. 271. ISBN 978-3-8261-0077-2.  Retrieved on June 12, 2009 through Google Book Search.
  3. ^ Smith T. A. (1977). "Phenethylamine and related compounds in plants". Phytochem. 16: 9–18. doi:10.1016/0031-9422(77)83004-5. 
  4. ^ Mitchell S. D.; Firmin J. L.; Gray D. O. (1984). "Enhanced 3-methoxytyramine levels in crown gall tumours and other undifferentiated plant tissues". Biochem J. 221: 891–5. doi:10.1042/bj2210891.