3-Methoxytyramine
Chemical compound
From Wikipedia, the free encyclopedia
3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a human trace amine and the major metabolite of the monoamine neurotransmitter dopamine.[1][2] It is formed by the introduction of a methyl group to dopamine by the enzyme 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.
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| Names | |
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| Preferred IUPAC name
4-(2-Aminoethyl)-2-methoxyphenol | |
| Other names
3-O-Methyldopamine | |
| Identifiers | |
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| ECHA InfoCard | 100.122.789 |
| MeSH | 3-methoxytyramine |
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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).
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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]
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Biological activity
Originally thought to be physiologically inactive, 3-MT was subsequently found to act as an agonist of the rodent and human TAAR1.[1][9][2] 3-MT can induce weak hyperlocomotion in mice and this effect is partially attenuated in TAAR1 knockout mice.[2][10]