BETAYNE (OXYNEURINE, LYCINE), C5H13NO3  , a substance discovered in the sugar beet (Beta vulgaris) in 1869 by C . Scheibler (Bete, 1869, 2, p . 292) . It is also found in cotton seed, in the vetch and in wheat sprouts (E . Schulz and S . Frankfurt, Ber., 1893, z6, p . 2151) . It may be synthetically prepared by oxidizing choline with chromic acid (O . Liebreich, Ber., 1869, 2, 13), (CH3)3N(O.H)•CH2 •CH2OH-05H13NO3+H2O; by 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 alkali (P . Griess, Ber., 1895, 8, p . 1406) . It crystallizes from alcohol in large deliquescent crystals; and is readily soluble in water, but insoluble in ether .

It is a weak

base . As is shown by the various syntheses of the base, it is the methyl hydroxide of dimethyl glycocoll . This free base readily loses water on heating and gives an 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 group in the a-position . A . Hantzsch (Ber., 1886, 19, p . 31) prepared the betaines of nicotinic, picolinic and collidine carboxylic acids from the potassium salts of the acids, by treatment with methyl iodide, followed by moist silver 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 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 nicotine by A . Pictet by oxidizing the methyl hydroxide of nicotine with potassium permanganate (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 (

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

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

carbon dioxide from the air . It is not poison-. ous . By continued boiling of its aqueous solution, it is resolved into glycol and trimethylamine . Neurine, trimethyl vinyl ammonium hydroxide (Gr. vsUpov, nerve), 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 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 .