3-Methoxytyramine
Names
4-(2-Aminoethyl)-2-methoxyphenol
3-O-Methyldopamine
Identifiers
Y3D model (JSmol)
NPubChem CID
CompTox Dashboard (EPA)
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
167.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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]
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 metaboliteofdopamine.[1]
Biosynthetic pathways for catecholamines and trace amines in the human brain[6][7][8]
Anabolism
(tyrosine→epinephrine)
Catabolism/
metabolites
norepinephrine:
epinephrine:
anabolism:
catabolism:
Synthetic and natural‡
Agonists‡
Neutral antagonists
Neutral antagonists
Inverse agonists‡
† References for all endogenous human TAAR1 ligands are provided at List of trace amines
‡ References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see TAAR for references.
Stimulants: Phenylethanolamine
Catecholamines
(and close relatives)
Miscellaneous
