CHOLINE AND ALLIED SUBSTANCES 67 



Honda [1911] first separates a good deal of the latter base by means 

 of its acid tartrate, which is less soluble than the muscarine salt. The 

 discovery of a muscarine salt which is less soluble than the corres- 

 ponding choline salt would greatly facilitate the preparation of pure 

 muscarine. 



The fate of pseudo-musczrme. (from choline) in the animal organism 

 has been investigated by Fiihner [1908, I ; 1909]. The lethal dose for 

 rabbits of 1-5 kilo, is O'3-O'5 grm. by the mouth and 0^04 -0*05 grm. 

 subcutaneousty ; the drug is partly secreted in the urine unchanged 

 (in the toad the whole is so excreted). In this respect ^seudo-muscarine 

 resembles betaine and differs from choline ; it is not a " Baustein ". 



Harmsen has concluded that the muscarine content of Amanita 

 muscaria is quite insufficient to account for the poisonous effects of 

 eating this fungus and considers that the effect is mainly due to a 

 complex toxin insoluble in alcohol and not counteracted by atropine. 

 From an allied species Amanita phalloides, Abel and Ford [1906] 

 have prepared a haemolysin which they regard as a nitrogenous 

 glucoside. 



Muscarine occurs in small quantity in Amanita pantherina and in Bol- 

 etus luridus (Boehm [1885, I, under choline]). Brieger [1885, i, p. 48, 

 Ch. I] isolated from putrid codfish a platinichloride (C 5 H U O 2 N) 2 PtCl 6 ; 

 the physiological action of the base was that of muscarine. The physi- 

 ological action of synthetic bases allied to muscarine has been described 

 by Schmidt [1891, 1904, I, under choline]; Brabant [1913] has re- 

 cently synthesised /3-homo-muscarine (CH 3 ) 3 N(OH)CH 2 . CH 2 . CHO. 



Trimethylamine Oxide, (CH 3 ) 3 NO. 



This base, the only member of its class known to occur naturally, 

 was isolated by Suwa [1909, I, 2] from the muscles of Acanthias vul- 

 garis. One dozen of this fish, yielding 23 kilos, of muscle, gave 20 

 grm. of the hydrochloride of trimethylamine oxide, together with a 

 quantity of betaine, but hardly any creatine, or creatinine. 



The hydrochloride melts at 205-210, the pier ate forms thin needles, mp. 197, sparingly 

 soluble in ethyl alcohol and cold water ; the platinichloride forms rhombic leaflets, mp. 

 214 ; the aurichloride C 3 H 9 ON . HAuCl 4 , mp. 250, is sparingly soluble in hot water. 



In concentrated aqueous solutions of the hydrochloride alcoholic solutions of mercury 

 and cadmium chlorides precipitate C 3 H 10 ONC1 . 4HgCl 2 . H 2 O and C ; ,H 10 ONC1 . CdCL 

 respectively. 



By putrefaction and also (at least in part) in the organism of the 

 rabbit, trimethylamine oxide is reduced to trimethylamine from which 

 it can be produced by oxidation with hydrogen peroxide. 



5* 



