50 THE SIMPLER NATURAL BASES 



basic properties are more completely neutralised by the carboxyl-group, 

 which is probably the reason for their physiological inertness (com- 

 pare also the section on w-amino-acids, p. 33). Brieger found that 

 10 mg. of his hydrochloride arrested the heart of a frog in diastole. 

 In rabbits 0-05-0-3 grm. produced mydriasis, salivation, clonic con- 

 vulsions, often violent lowering of body temperature, dyspnoea, 

 paralysis and ultimately (after several hours) death with the heart in 

 diastole (Brieger [1886, I, pp. 29-31 ; Ch. I]). 



Brieger obtained two other bases of the composition C 7 H 17 O 2 N. One of these is 

 gadinine, obtained from putrid cod fish (Bocklisch [1885, Ch. 1], Brieger [1885, i, p. 49 ; 

 Ch. IJ) and isolated as platinichloride. It " appeared " to be physiologically inert and the 

 solution of the hydrochloride yielded a precipitate with picric acid, but not with gold chloride. 

 Against these differences we may set the fact that the hydrochloride, like that of y-butyro- 

 betaine and of betaine itself, was insoluble in absolute alcohol. 



The other base C 7 H 17 O 2 N is typhotoxine, obtained from cultures of typhoid bacilli 

 (Brieger [1886, i, p. 86 ; Ch. I]). The melting point of the aurichloride was identical with 

 that of the ptomaine from putrid horse meat (176). Typhotoxine, however, yielded a spar- 

 ingly soluble picrate, a yellow coloration with diazobenzene sulphonic acid, and amorphous 

 precipitates with potassium tri-iodide, potassium mercuric iodide and potassium cadmium 

 iodide. The physiological action of typhotoxine was also somewhat different from that of 

 the ptomaine from putrid horse meat. 



It does not seem wholly impossible, however, that all three bases were identical with 

 y-butyro-betaine. 



Carnitine (Novaine, a-Hydroxy-7-butyro-betaine), 

 O CO, 



ff H "\ " XT' \r't-IO'H' 



iv^riojo i \ /\^ii\jr\.. 



X CH 2 CH/ 



A A 



Carnitine, C 7 H 15 O 3 N, is a hydroxy-derivative of the base described 

 in the previous section arid was discovered in extract of muscle by 

 Gulewitsch and Krimberg [1905]. A few months later Kutscher 

 [1905] obtained from Liebig's extract of meat a base " novain " 

 which Krimberg [1908, i] proved to be identical with carnitine; the 

 identity has been admitted by Kutscher's pupils, if not explicitly by 

 Kutscher himself. According to Kutscher a base C 7 H 15 O 2 N, isolated 

 by Dombrowski [1902] from normal human urine, was identical with 

 novaine ; Kutscher thinks that in most cases (except in the dog) 

 novaine passes into the urine as its reduction product reducto-novaine. 

 Both carnitine and novaine were found by their discoverers to yield 

 trimethylamine and crotonic acid (or an isomeride) on heating with 

 baryta. By boiling with phosphorus and hydriodic acid Krimberg 

 [1907, 2] reduced carnitine to 7-butyro-betaine. 



The only doubt now remaining was with regard to the position of 

 the hydroxyl group in carnitine. Krimberg at first favoured the 

 /9-position, but y3-hydroxy-7-butyro-betaine 



