Names | |
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Preferred IUPAC name
4-(2-Aminoethyl)-2-methoxyphenol | |
Other names
3-O-Methyldopamine | |
Identifiers | |
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3D model (JSmol) |
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ChEBI | |
ChemSpider |
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ECHA InfoCard | 100.122.789 |
MeSH | 3-methoxytyramine |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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). |
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]
3-Methoxytyramine
primary
pathway
brain
CYP2D6
minor
In humans, catecholamines and phenethylaminergic trace amines are derived from the amino acid L-phenylalanine.
pathway |
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catecholamines |
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tryptophan→serotonin |
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serotonin→melatonin |
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TAAR1 |
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TAAR2 |
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TAAR5 |
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‹See TfM›† 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.
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Phenethylamines |
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Amphetamines |
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Phentermines |
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Cathinones |
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Phenylisobutylamines |
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Phenylalkylpyrrolidines |
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Catecholamines (and close relatives) |
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Miscellaneous |
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