N-methyltyramine
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| Names | |
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IUPAC name
4-[2-(Methylamino)ethyl]phenol
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| Other names
Methyl-4-tyramine; 4-Hydroxy-N-methylphenethylamine; p-(2-Methylaminoethyl)phenol
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
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| ECHA InfoCard | 100.006.120 |
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PubChem CID
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| Properties | |
| C9H13NO | |
| Molar mass | 151.21 g·mol−1 |
| Appearance | colorless crystalline solid |
| Density | 1.03 g/mL |
| Melting point | 130 to 131 °C (266 to 268 °F; 403 to 404 K) |
| Boiling point | 271 °C (520 °F; 544 K) (183-185 °C at 9mm; 135 °C at 0.05 mm) |
| moderately soluble in water | |
| Hazards | |
| Flash point | 120 °C (248 °F; 393 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
N-Methyltyramine (NMT), also known as 4-hydroxy-N-methylphenethylamine, is a human trace amine and natural phenethylamine alkaloid found in a variety of plants. As the name implies, it is the N-methyl analog of tyramine, which is a well-known biogenic trace amine with which NMT shares many pharmacological properties. Biosynthetically, NMT is produced by the N-methylation of tyramine via the action of the enzyme phenylethanolamine N-methyltransferase in humans and tyramine N-methyltransferase in plants.
N-methyltyramine seems to be quite widely distributed in plants.
NMT was isolated as a natural product for the first time, from germinating barley roots, by Kirkwood and Marion in 1950. These chemists found that 600 g of barley, after germination and 10-day growth, yielded 168 mg of N-methyltyramine. Since barley, via its conversion to malt, is used extensively in the production of beer, beer and malt have been examined by several groups of investigators for the presence of NMT. Citing a 1965 study by McFarlane, Poocharoen reported that beer contained ~ 5–8 mg/L of NMT. The NMT content of various malts and malt fractions was extensively studied by Poocharoen himself, who also provided a good coverage of related literature up to 1983. This researcher found a mean concentration of NMT in raw barley of ~ 5 μg/g; in green malts (i.e. barley that had been soaked in water for 2 days then germinated for 4 days), the mean concentration was ~ 21 μg/g, and in kilned malts (i.e. green malts that had been heated in a kiln for 1–2 days) the mean concentration was ~ 27 μg/g. When only green malt roots were examined, their mean content of NMT was ~ 1530 μg/g, whereas the mean level in kilned malt roots was ~ 1960 μg/g.
Studies of Acacia species have shown the presence of significant levels of NMT in their leaves: ~ 240-1240 ppm (or μg/g) in A. rigidula and ~ 190-750 ppm in A. berlandieri. The seeds of A. schweinfurthii yielded 440 μg/g of NMT.
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