Trigonelline
Chemical compound / From Wikipedia, the free encyclopedia
Trigonelline is an alkaloid with chemical formula C7H7NO2. It is a zwitterion formed by the methylation of the nitrogen atom of niacin (vitamin B3). Trigonelline is a product of niacin metabolism that is excreted in the urine of mammals.[1]
Quick Facts Names, Identifiers ...
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Preferred IUPAC name
1-Methylpyridin-1-ium-3-carboxylate | |
Other names
Nicotinic acid N-methylbetaine Coffearine Caffearine Gynesine Trigenolline | |
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ECHA InfoCard | 100.007.838 |
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Properties | |
C7H7NO2 | |
Molar mass | 137.138 g·mol−1 |
Melting point | 230 to 233 °C (446 to 451 °F; 503 to 506 K) (monohydrate)[contradictory] 258–259 °C (hydrochloride) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trigonelline occurs in many plants. It has been isolated from the Japanese radish[2] (Raphanus sativus cv. Sakurajima Daikon), fenugreek seeds (Trigonella foenum-graecum, hence the name),[3] garden peas, hemp seed, oats,[4] potatoes, Stachys species, dahlia,[5] Strophanthus species,[6] and Dichapetalum cymosum.[7] Trigonelline is also found in coffee.[8] Higher levels of trigonelline are found in arabica coffee.
Holtz, Kutscher, and Theilmann have recorded its presence in a number of animals.[9]