BETAINES 51 



/o co\ 



(CH 3 ) 3 N/ J>CH 2 



CH 2 CHOH 



has been synthesised by Rollett [1910] and by Engeland [1910 2] 

 and was found to differ from carnitine, which is therefore most likely 

 a-hydroxy-7-butyrobetaine 



i N CHOH. 



\CH 2 .CH 2 / 



The a-position of the hydroxyl group seems also to result from the 

 oxidation of carnitine by calcium permanganate (Engeland [1909, I]) 

 to /?-homobetaine 



o co 



(CH 3 ) 3 : N/ 



\CH 2 CH 2 



Racemic carnitine has probably been obtained by Fischer and Goddertz 

 [1910] from 7-phthalimido-a-bromobutyric acid; the melting point 

 of the platinichloride agrees with that of natural carnitine, but the 

 aurichloride has a much higher melting point. Carnitine may be pre- 

 pared from meat extract by Gulewitsch and Krimberg's method, or by 

 that of Kutscher ; the former method, in which the filtrate from carno- 

 sine is precipitated with potassium bismuth iodide, gives apparently 

 the better yield (1-3 per cent, of the Liebig's extract employed). 

 Smorodinzew [1913; Ch. II, carnosine] obtained O'O2 per cent, of 

 carnitine from fresh horse meat. Carnitine probably passes unchanged 

 into the urine, for Kutscher and Lohmann [1906, 2] could isolate 

 novaine ( = carnitine) from the urine of a dog fed on meat extract but 

 not from normal dog's urine. In the rabbit carnitine is, perhaps, re- 

 duced to butyrobetaine, according to Engeland [1908, I]. The physi- 

 ological action of novaine ( = carnitine) has been studied by Kutscher 

 and Lohmann [1906, I]. One gram, given hypodermically to a cat, 

 produced serious disturbance of the digestive tract ; given intravenously 

 novaine has a slight depressor action. Oblitine, a base obtained by 

 Kutscher from meat extract, is according to Krimberg merely carnitine 

 ethyl ester formed from carnitine during Kutscher's process of extrac- 

 tion (see appendix). 



Reductonovaine C 7 H 15 ON was isolated as the aurichloride 

 C 7 H 16 ONC1, AuCl 3 , mp. 155-180, from women's urine by Kutscher 

 [1907, 2] who regards it as formed by loss of water from novaine to 

 which it stands in the same relation as neurine to choline. 



4* 



