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BETAYNE (OXYNEURINE, LYCINE), C5H13NO3

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Originally appearing in Volume V03, Page 828 of the 1911 Encyclopedia Britannica.
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BETAYNE (OXYNEURINE, LYCINE), C5H13NO3 , a substance discovered in the See also:sugar See also:beet (Beta vulgaris) in 1869 by C. Scheibler (Bete, 1869, 2, p. 292). It is also found in See also:cotton See also:seed, in the See also:vetch and in See also:wheat sprouts (E. Schulz and S. Frankfurt, Ber., 1893, z6, p. 2151). It may be synthetically prepared by oxidizing choline with chromic See also:acid (O. Liebreich, Ber., 1869, 2, 13), (See also:CH3)3N(O.H)•CH2 •CH2OH-05H13NO3+See also:H2O; by See also:heating trimethylamine with monochloracetic acid (Liebreich), (CH3)3N+CH2C1•000H= (CH3)3N(Cl)•CH2.000H (betaine hydrochloride); and by heating amino-acetic acid (glycocoll) with methyl iodide in the presence of an See also:alkali (P. Griess, Ber., 1895, 8, p. 1406). It crystallizes from See also:alcohol in large deliquescent crystals; and is readily soluble in See also:water, but insoluble in See also:ether.

It is a weak See also:

base. As is shown by the various syntheses of the base, it is the methyl hydroxide of dimethyl glycocoll. This See also:free base readily loses water on heating and gives an See also:internal anhydride of constitution (CH3)3N< 0I2>CO3 which is the type of the so-called " betaines." These organic beta'ines are internal anhydrides of carboxylic acids, which contain an ammonium hydroxide See also:group in the a-position. A. Hantzsch (Ber., 1886, 19, p. 31) prepared the betaines of nicotinic, picolinic and collidine carboxylic acids from the See also:potassium salts of the acids, by treatment with methyl iodide, followed by moist See also:silver See also:oxide. The reaction may be shown as follows: Cr `COvK OCOiCHs Li0 11Rr ~ HaHaC— O The methyl betaine of nicotinic acid is identical with the See also:alkaloid trigonelline, which was discovered in 1885 by E. Jahns in the seeds of Trigonella faenum-graecum (Ber., 1885, 18, p. 2518). It has also been obtained from See also:nicotine by A. Pictet by oxidizing the methyl hydroxide of nicotine with potassium permanganate (See also:Bee., 1897, 30, p. 2117).

Substances closely related to betaine are choline, neurine and muscarine. Choline (bilineurine, sincaline), (Gr. xoX,, bile), CSH1SNO2 or HO•CH2•CH2•N(CH3)3.OH, first isolated by A. Strecker in 1862 (See also:

Ann. 123, p. 353; 148, p. 76), is found in the bile, in See also:brain substance, and in yolk of See also:egg in the See also:form of lecithin, a complex ester of See also:glycerin with phosphoric acid and the fatty acids. It is also found in See also:combination with sinapic acid in sinapin, the See also:glucoside obtained from See also:white See also:mustard, and can be obtained from this glucoside by See also:hydrolysis with baryta water, C16H23NO5+2H20 = C5H15NO2 + C„HI205. Sinapin. Choline. Sinapic acid. It can be synthetically prepared by the See also:action of trimethylamine on an aqueous See also:solution of See also:ethylene oxide (A. See also:Wurtz, Ann.

Suppl., 1868, 6, p. 201). If forms deliquescent crystals of strongly alkaline reaction, and absorbs See also:

carbon dioxide from the See also:air. It is not See also:poison-. ous. By continued boiling of its aqueous solution, it is resolved into glycol and trimethylamine. Neurine, trimethyl vinyl ammonium hydroxide (Gr. vsUpov, See also:nerve), See also:CH2:CH•N(CH3)3.OH, is a product of the putrefaction of albumen. It may be prepared by the action of moist silver oxide on ethylene dibromide and trimethylamine, CH2Br•CH2Br–>CH2Br.CH2•N(CH3)3Br-->CH2:CH•N(CH3)3•OH. It is a crystalline solid, very soluble in water, and is strongly basic and very poisonous. M uscarine, C5H15NO3, is an exceedingly poisonous substance found in many See also:fungi. It may be obtained synthetic-ally by oxidizing choline with dilute nitric acid (O. Schmiedeberg, Jahresb., 1876, p. 804).

The exact constitution has not yet been definitely determined.

End of Article: BETAYNE (OXYNEURINE, LYCINE), C5H13NO3

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