3-Methoxytyramine

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 ?)

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]

  1. ^ a b 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.