Trigonelline

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Trigonelline
Trigonelline Structural Formula V2.svg
Names
Preferred IUPAC name
1-Methylpyridin-1-ium-3-carboxylate
Other names
Nicotinic acid N-methylbetaine
Coffearine
Caffearine
Gynesine
Trigenolline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.838 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3 Yes check.svgY
    Key: WWNNZCOKKKDOPX-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
    Key: WWNNZCOKKKDOPX-UHFFFAOYAV
  • O=C([O-])c1ccc[n+](c1)C
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 is an alkaloid with chemical formula C 7 H 7 N O 2. 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]

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]

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. [10]

Related Research Articles

<span class="mw-page-title-main">Alkaloid</span> Class of naturally occurring chemical compounds

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. Rarer still, they may contain elements such as phosphorus, chlorine, and bromine.

<span class="mw-page-title-main">Niacin</span> Organic compound and a form of vitamin B3

Niacin, also known as nicotinic acid, is an organic compound and a vitamer of vitamin B3, an essential human nutrient. It is produced by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a variety of whole and processed foods, with highest contents in fortified packaged foods, meat, poultry, red fish such as tuna and salmon, lesser amounts in nuts, legumes and seeds. Niacin as a dietary supplement is used to treat pellagra, a disease caused by niacin deficiency. Signs and symptoms of pellagra include skin and mouth lesions, anemia, headaches, and tiredness. Many countries mandate its addition to wheat flour or other food grains, thereby reducing the risk of pellagra.

<span class="mw-page-title-main">Fenugreek</span> Species of flowering plant

Fenugreek is an annual plant in the family Fabaceae, with leaves consisting of three small obovate to oblong leaflets. It is cultivated worldwide as a semiarid crop. Its leaves and seeds are common ingredients in dishes from the Indian subcontinent, and have been used as a culinary ingredient since ancient times. Its use as a food ingredient in small quantities is safe.

<span class="mw-page-title-main">Coniine</span> Chemical compound

Coniine is a poisonous chemical compound, an alkaloid present in and isolable from poison hemlock (Conium maculatum), where its presence has been a source of significant economic, medical, and historico-cultural interest; coniine is also produced by the yellow pitcher plant (Sarracenia flava), and fool's parsley (Aethusa cynapium). Its ingestion and extended exposure are toxic to humans and all classes of livestock; its mechanism of poisoning involves disruption of the central nervous system, with death caused by respiratory paralysis. The biosynthesis of coniine contains as its penultimate step the non-enzymatic cyclisation of 5-oxooctylamine to γ-coniceine, a Schiff base differing from coniine only by its carbon-nitrogen double bond in the ring. This pathway results in natural coniine that is a mixture—a racemate—composed of two enantiomers, the stereoisomers (S)-(+)-coniine and (R)-(−)-coniine, depending on the direction taken by the chain that branches from the ring. Both enantiomers are toxic, with the (R)-enantiomer being the more biologically active and toxic of the two in general. Coniine holds a place in organic chemistry history as being the first of the important class of alkaloids to be synthesized, by Albert Ladenburg in 1886, and it has been synthesized in the laboratory in a number of unique ways through to modern times.

<span class="mw-page-title-main">Piperine</span> Alkaloid responsible for the pungency of black pepper

Piperine, possibly along with its isomer chavicine, is the compound responsible for the pungency of black pepper and long pepper. It has been used in some forms of traditional medicine.

The Fischer oxazole synthesis is a chemical synthesis of an oxazole from a cyanohydrin and an aldehyde in the presence of anhydrous hydrochloric acid. This method was discovered by Emil Fischer in 1896. The cyanohydrin itself is derived from a separate aldehyde. The reactants of the oxazole synthesis itself, the cyanohydrin of an aldehyde and the other aldehyde itself, are usually present in equimolar amounts. Both reactants usually have an aromatic group, which appear at specific positions on the resulting heterocycle.

<span class="mw-page-title-main">Phenazine</span> Chemical compound

Phenazine is an organic compound with the formula (C6H4)2N2. It is a dibenzo annulated pyrazine, and the parent substance of many dyestuffs, such as the toluylene red, indulines, and safranines (and the closely related eurhodines). Phenazine crystallizes in yellow needles, which are only sparingly soluble in alcohol. Sulfuric acid dissolves it, forming a deep-red solution.

<span class="mw-page-title-main">Arecoline</span> Stimulant alkaloid

Arecoline is a nicotinic acid-based mild parasympathomimetic stimulant alkaloid found in the areca nut, the fruit of the areca palm. It is an odourless oily liquid. It can bring a sense of enhanced alertness and energy along with mild feelings of euphoria and relaxation.

<span class="mw-page-title-main">1-Naphthylamine</span> Chemical compound

1-Naphthylamine is an aromatic amine derived from naphthalene. It can cause bladder cancer. It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and turns brown on exposure to air. It is the precursor to a variety of dyes.

<span class="mw-page-title-main">Methyllycaconitine</span> Chemical compound

Methyllycaconitine (MLA) is a diterpenoid alkaloid found in many species of Delphinium (larkspurs). In common with many other diterpenoid alkaloids, it is toxic to animals, although the acute toxicity varies with species. Methyllycaconitine was identified one of the principal toxins in larkspurs responsible for livestock poisoning in the mountain rangelands of North America. Methyllycaconitine has been explored as a possible therapeutic agent for the treatment of spastic paralysis, and it has been shown to have insecticidal properties. It has become an important molecular probe for studying the pharmacology of the nicotinic acetylcholine receptor.

Chiral resolution, or enantiomeric resolution, is a process in stereochemistry for the separation of racemic mixture into their enantiomers. It is an important tool in the production of optically active compounds, including drugs. Another term with the same meaning is optical resolution.

<span class="mw-page-title-main">Free base</span> Pure molecular form of an amine, as opposed to its protonated salt form

Free base is a descriptor for the neutral form of an amine commonly used in reference to illicit drugs. The amine is often an alkaloid, such as nicotine, cocaine, morphine, and ephedrine, or derivatives thereof. Freebasing is a more efficient method of self-administering alkaloids via the smoking route.

<span class="mw-page-title-main">Nicotinyl alcohol</span> Chemical compound

Nicotinyl alcohol (pyridylcarbinol) is a niacin derivative used as a hypolipidemic agent and as a vasodilator. It causes flushing and may decrease blood pressure.

<span class="mw-page-title-main">Chloroauric acid</span> Chemical compound

Chloroauric acid is an inorganic compound with the chemical formula H[AuCl4]. It forms hydrates H[AuCl4nH2O. Both the trihydrate and tetrahydrate are known. Both are orange-yellow solids consisting of the planar [AuCl4] anion. Often chloroauric acid is handled as a solution, such as those obtained by dissolution of gold in aqua regia. These solutions can be converted to other gold complexes or reduced to metallic gold or gold nanoparticles.

<i>Alstonia constricta</i> Species of tree

Alstonia constricta, commonly known as quinine bush or bitterbark, is an Australian endemic shrub or small tree of the family Apocynaceae.

<span class="mw-page-title-main">Scopoletin</span> Chemical compound

Scopoletin is a coumarin found in the root of plants in the genus Scopolia such as Scopolia carniolica and Scopolia japonica, in chicory, in Artemisia scoparia, in the roots and leaves of stinging nettle, in the passion flower, in Brunfelsia, in Viburnum prunifolium, in Solanum nigrum, in Datura metel, in Mallotus resinosus, or and in Kleinhovia hospita. It can also be found in fenugreek, vinegar, some whiskies or in dandelion coffee. A similar coumarin is scoparone. Scopoletin is highly fluorescent when dissolved in DMSO or water and is regularly used as a fluorimetric assay for the detection of hydrogen peroxide in conjunction with horseradish peroxidase. When oxidized, its fluorescence is strongly suppressed.

<span class="mw-page-title-main">Thorium(IV) nitrate</span> Chemical compound

Thorium(IV) nitrate is a chemical compound, a salt of thorium and nitric acid with the formula Th(NO3)4. A white solid in its anhydrous form, it can form tetra- and pentahydrates. As a salt of thorium it is weakly radioactive.

1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3) into hydrophobic compounds possessing nucleophilic functional groups, for example hydroxy groups (as in the case of β-cyclodextrin) or amino groups (as in the case of polymethine dyes). In such, the sulfobutyl group is present as neutral sodium salt and considerably increases the water solubility of the derivatives.

<span class="mw-page-title-main">Precoccinelline</span> Chemical compound

Precoccinelline is an alkaloid produced by the Coccinella septempunctata, also known as the seven-spot ladybird. The alkaloid is released from the joints in C. septempunctata legs when it is provoked to deter predators such as ants or birds. It binds to both insect and mammalian nicotinic acetylcholine receptors, giving it use as an insecticide or as a therapy to treat drug dependence.

<span class="mw-page-title-main">Bismuthyl (ion)</span> Chemical compound

Bismuthyl is an inorganic oxygen-containing singly charged ion with the chemical formula BiO+, and is an oxycation of bismuth in the +3 oxidation state. Most often it is formed during the hydrolysis of trivalent bismuth salts, primarily nitrate, chloride and other halides. In chemical compounds, bismuthyl plays the role of a monovalent cation.

References

  1. Merck Index , 11th Edition, 9606.
  2. Kuroda, Rei; Kazumura, Kimiko; Ushikata, Miki; Minami, Yuji; Kajiya, Katsuko (2018). "Elucidating the Improvement in Vascular Endothelial Function from Sakurajima Daikon and its Mechanism of Action: A Comparative Study with Raphanus sativus". Journal of Agricultural and Food Chemistry. 66 (33): 8714–8721. doi:10.1021/acs.jafc.8b01750. PMID   30037222. S2CID   51712881.
  3. Ouzir, Mounir; El Bairi, Khalid; Amzazi, Saaïd (2016). "Toxicological properties of fenugreek (Trigonella foenum graecum)". Food and Chemical Toxicology. 96: 145–154. doi:10.1016/j.fct.2016.08.003. PMID   27498339.
  4. Schulze and Frankfurt, Ber., 1894, 27, 709.
  5. Schulze and Trier, Zeit. physiol. Chem., 1912, 76, 258.
  6. Thoms, Ber., 1891, 31, 271, 404.
  7. Rimington, Onderstepoort J., 1935, 5, 81.
  8. 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.
  9. Zeit. Biol., 1924, 81, 57.
  10. Anderson Henry, Thomas (1949). The Plant Alkaloids (4th ed.). Philadelphia: The Blakiston Company. pp. 7–8.