Chemistry:3-Methoxytyramine

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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
MeSH 3-methoxytyramine
UNII
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
Tracking categories (test):

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.

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

Occurrence

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] {{Annotated image 4 | caption = {{{caption|In humans, catecholamines and phenethylaminergic trace amines are derived from the amino acid {{nowrap|L-phenylalanine}}.}}} | header_background = #F0F8FF | header = Biosynthetic pathways for catecholamines and trace amines in the human brain<ref name="Trace amine template 1">Broadley KJ (March 2010). "The vascular effects of trace amines and amphetamines". Pharmacol. Ther. 125 (3): 363–375. doi:10.1016/j.pharmthera.2009.11.005. PMID 19948186. </ref>[6][7] | alt = Graphic of catecholamine and trace amine biosynthesis | image = Catecholamine and trace amine biosynthesis.png | image-width = 580 | image-left = 5 | image-top = 0 | align = left | width = 590 | height = 585 | annot-font-size = 14 | annot-text-align = center | annotations =

{{annotation|50|565|{{if pagename|Adrenaline=Adrenaline|Epinephrine=Epinephrine|Catecholamine=Epinephrine|other=Epinephrine}}}}

{{annotation|245|60|{{if pagename|Phenethylamine=Phenethylamine|Trace amine=Phenethylamine|Neurobiological effects of physical exercise={{highlight|Phenethylamine}}|other=Phenethylamine}}}}

{{annotation|245|565|{{if pagename|Norepinephrine=Norepinephrine|Adrenaline=Noradrenaline|Catecholamine=Norepinephrine|other=Norepinephrine}}}}

{{annotation|440|295|p-Octopamine}}}}

3-Methoxytyramine
primary
pathway
brain
CYP2D6
minor
pathway

See also

References

  1. 1.0 1.1 1.2 "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomed. Pharmacother. 83: 439–449. October 2016. doi:10.1016/j.biopha.2016.07.002. PMID 27424325. 
  2. "The dopamine metabolite 3-methoxytyramine is a neuromodulator". PLOS ONE 5 (10): e13452. 2010. doi:10.1371/journal.pone.0013452. PMID 20976142. Bibcode2010PLoSO...513452S. 
  3. Neuwinger, Hans Dieter (1996). "Cactaceae". African ethnobotany: poisons and drugs: chemistry, pharmacology, toxicology. CRC Press. pp. 271. ISBN 978-3-8261-0077-2. https://books.google.com/books?id=_j8ueEmakD0C&pg=PA271.  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. doi:10.1016/0031-9422(77)83004-5. Bibcode1977PChem..16....9S. 
  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. PMID 6477503. 
  6. "A renaissance in trace amines inspired by a novel GPCR family". Trends Pharmacol. Sci. 26 (5): 274–281. May 2005. doi:10.1016/j.tips.2005.03.007. PMID 15860375. 
  7. "The endogenous substrates of brain CYP2D". Eur. J. Pharmacol. 724: 211–218. February 2014. doi:10.1016/j.ejphar.2013.12.025. PMID 24374199. 

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