Trigonelline
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470614745
| Name = Trigonelline
| ImageFile = Trigonelline Structural Formula V2.svg
| ImageClass = skin-invert-image
| ImageSize = 120px
| ImageName =
| PIN = 1-Methylpyridin-1-ium-3-carboxylate
| OtherNames = Nicotinic acid N-methylbetaine
Coffearine
Caffearine
Gynesine
Trigenolline
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5369
| PubChem = 5570
| InChI = 1/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
| InChIKey = WWNNZCOKKKDOPX-UHFFFAOYAV
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 350675
| ChEMBL2_Ref = {{ebicite|correct|EBI}}
| ChEMBL2 = 489961
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WWNNZCOKKKDOPX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 535-83-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3NQ9N60I00
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 18123
| SMILES = O=C([O-])c1ccc[n+](c1)C
}}
|Section2={{Chembox Properties
| C=7 | H=7 | O=2 | N=1
| Density =
| MeltingPtC = 230 to 233
| MeltingPt_notes = (monohydrate){{contradict-inline|reason=text has a different value|date=September 2015}}
258–259 °C (hydrochloride)
}}
}}
Trigonelline is an alkaloid with chemical formula {{chem2|C7H7NO2|auto=1}}. 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.Merck Index, 11th Edition, 9606.
Trigonelline occurs in many plants. It has been isolated from the Japanese radish{{cite journal | doi=10.1021/acs.jafc.8b01750 | pmid=30037222 | title=Elucidating the Improvement in Vascular Endothelial Function from Sakurajima Daikon and its Mechanism of Action: A Comparative Study with Raphanus sativus | journal=Journal of Agricultural and Food Chemistry | volume=66 | issue=33 | pages=8714–8721 | year=2018 | last1=Kuroda | first1=Rei | last2=Kazumura | first2=Kimiko | last3=Ushikata | first3=Miki | last4=Minami | first4=Yuji | last5=Kajiya | first5=Katsuko | s2cid=51712881 }} (Raphanus sativus cv. Sakurajima Daikon), fenugreek seeds (Trigonella foenum-graecum, hence the name),{{cite journal | doi=10.1016/j.fct.2016.08.003| pmid=27498339| title=Toxicological properties of fenugreek (Trigonella foenum graecum)| journal=Food and Chemical Toxicology| volume=96| pages=145–154| year=2016| last1=Ouzir| first1=Mounir| last2=El Bairi| first2=Khalid| last3=Amzazi| first3=Saaïd}} garden peas, hemp seed, oats,Schulze and Frankfurt, Ber., 1894, 27, 709. potatoes, Stachys species, dahlia,Schulze and Trier, Zeit. physiol. Chem., 1912, 76, 258. Strophanthus species,Thoms, Ber., 1891, 31, 271, 404. and Dichapetalum cymosum.Rimington, Onderstepoort J., 1935, 5, 81. Trigonelline is also found in coffee.Gorter, Annalen, 1910, 372, 237; cf. Polstorff, Chem. Soc. Abstr., 1910, ii, 234; Palladino, ibid, 1894, ii, 214; 1895, i, 629; Graf, ibid, 1904, i, 915; Nottbohm and Mayer, Zeit. Unters. Lebensmitt., 1931, 61, 429. Higher levels of trigonelline are found in arabica coffee.
Holtz, Kutscher, and Theilmann have recorded its presence in a number of animals.Zeit. Biol., 1924, 81, 57.
Chemistry
Trigonelline crystallizes as a monohydrate from alcohol in hygroscopic prisms (m.p. 130 °C or 218 °C [dry, dec.]). It is readily soluble in water or warm alcohol, less so in cold alcohol, and slightly so in chloroform or ether. The salts crystallize well, the monohydrochloride, in leaflets, sparingly soluble in dry alcohol. The picrate forms shining prisms (m.p. 198−200 °C) soluble in water but sparingly soluble in dry alcohol or ether. The alkaloid forms several aurichlorides: the normal salt, B•HCl•AuCl3, is precipitated when excess of gold chloride is added to the hydrochloride, and, after crystallization from dilute hydrochloric acid containing some gold chloride, has m.p. 198 °C. Crystallized from water or very dilute hydrochloric acid, slender needles of B4•3 HAuCl4 (m.p. 186 °C) are obtained.
When trigonelline is heated in closed tubes with barium hydroxide at 120 °C, it gives rise to methylamine, and, if treated similarly with hydrochloric acid at 260 °C creates chloromethane and nicotinic acid (a form of vitamin B3). Trigonelline is a methyl betaine of nicotinic acid.{{cite book|title=The Plant Alkaloids|pages=7–8|first1=Thomas|last1=Anderson Henry|edition=4th|year=1949|publisher=The Blakiston Company|location=Philadelphia}}