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3-Methoxytyramine

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3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a human trace amine that occurs as a metabolite of the neurotransmitter dopamine.[1] It is 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.

3-Methoxytyramine
Skeletal formula of 3-methoxytyramine
Ball-and-stick model of the 3-methoxytyramine molecule
Names
Preferred IUPAC name
4-(2-Aminoethyl)-2-methoxyphenol
Other names
3-O-Methyldopamine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.122.789 Edit this at Wikidata
MeSH 3-methoxytyramine
UNII
  • InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3 ☒N
    Key: DIVQKHQLANKJQO-UHFFFAOYSA-N ☒N
  • InChI=1/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
    Key: DIVQKHQLANKJQO-UHFFFAOYAB
  • COc1cc(ccc1O)CCN
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 verify (what is checkY☒N ?)

Originally thought to be physiologically inactive, 3-MT has recently been shown to act as an agonist of human TAAR1.[1][2]

Occurrence

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3-Methoxytyramine occurs naturally in the prickly pear cactus (genus Opuntia),[3] and is in general widespread throughout the Cactaceae.[4] It has also been found in crown gall tumors on Nicotiana sp.[5]

In humans, 3-methoxytyramine is a trace amine that occurs as a metabolite of dopamine.[1]

Biosynthetic pathways for catecholamines and trace amines in the human brain[6][7][8]
 
In humans, catecholamines and phenethylaminergic trace amines are derived from the amino acid L-phenylalanine.

See also

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References

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  1. ^ a b c Khan MZ, Nawaz W (October 2016). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomed. Pharmacother. 83: 439–449. doi:10.1016/j.biopha.2016.07.002. PMID 27424325.
  2. ^ Sotnikova TD, Beaulieu JM, Espinoza S, et al. (2010). "The dopamine metabolite 3-methoxytyramine is a neuromodulator". PLOS ONE. 5 (10): e13452. Bibcode:2010PLoSO...513452S. doi:10.1371/journal.pone.0013452. PMC 2956650. PMID 20976142.
  3. ^ Neuwinger HD (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.
  4. ^ Smith T. A. (1977). "Phenethylamine and related compounds in plants". Phytochemistry. 16 (1): 9–18. Bibcode:1977PChem..16....9S. doi:10.1016/0031-9422(77)83004-5.
  5. ^ 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 (3): 891–5. doi:10.1042/bj2210891. PMC 1144120. PMID 6477503.
  6. ^ Broadley KJ (March 2010). "The vascular effects of trace amines and amphetamines". Pharmacology & Therapeutics. 125 (3): 363–375. doi:10.1016/j.pharmthera.2009.11.005. PMID 19948186.
  7. ^ Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends in Pharmacological Sciences. 26 (5): 274–281. doi:10.1016/j.tips.2005.03.007. PMID 15860375.
  8. ^ Wang X, Li J, Dong G, Yue J (February 2014). "The endogenous substrates of brain CYP2D". European Journal of Pharmacology. 724: 211–218. doi:10.1016/j.ejphar.2013.12.025. PMID 24374199.
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