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
ECHA InfoCard
 100.122.789 Edit this at Wikidata
IUPHAR/BPS
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
SMILES
  • 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 ?)

3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a human

catechol-O-methyltransferase (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.

Occurrence

3-Methoxytyramine occurs naturally in the

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]
Graphic of catecholamine and trace amine biosynthesis
The image above contains clickable links
In humans, catecholamines and phenethylaminergic trace amines are derived from the amino acid L-phenylalanine.

Biological activity

Originally thought to be physiologically inactive, 3-MT was subsequently found to act as an

knockout mice.[2][10]

See also

References

  1. ^
    PMID 27424325
    .
  2. ^
    PMID 21073468
    . The data support the hypothesis that TAAR1 inhibits locomotor activity via a down-modulation of dopamine neurotransmission (Lindemann et al. 2008) and that the overruling effect of blocking TAAR1 is a net increase in the firing rate of DA neurons (Bradaia et al. 2009). However, a more recent study by Sotnikova et al. (2010) reports that the major extracellular metabolite of dopamine, 3-methoxytyramine, which is an agonist at rat TAAR1 (Bunzow et al. 2001), can induce mild hyperactivity in normal mice and a complex set of abnormal involuntary movements in normal mice acutely depleted of dopamine, and that these effects were attenuated in TAAR1 knockout mice. These data suggest that TAAR1 activation may stimulate locomotor activity. Collectively, the data illustrate a complexity of TAAR1 neurobiology that is still not fully understood.
  3. Google Book Search
    .
  4. doi:10.1016/0031-9422(77)83004-5
    .
  5. PMID 6477503
    .
  6. PMID 19948186
    .
  7. PMID 15860375
    .
  8. PMID 24374199
    .
  9. PMID 20976142
    .
  10. PMID 20976142
    .
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