MYBATOXIN. 311 



The formulse of several muscarin compounds are herewith presented : 



(1) (2) (3) 



CH(OH)j COH CHjOH 



CHj CHj CHOH 



N(CHj),.OH l!f(CH3),.0H N(CH,)3.0H. 



MUSCAKIH. BETAIH ALII£EYD. Iso-uuscABm. 



It will be observed that very slight differences in the chemical 

 constitution of cholin, muscarin, betain and neurin are accompanied 

 by very great differences in the physiological action of these bases. 

 Thus, as pointed out by Schmidt, cholin may be considered as a pri- 

 mary alcohol and betain as a monobasic acid. Between these two 

 relatively non-poisonous bases is the intermediate oxidation product, 

 the aldehyde muscarin, which is highly poisonous. 



Again, it will be remembered that the artificial muscarin, formed by 

 the oxidation of cholin, had a markedly different physiological effect 

 on the intramuscular nerve endings and on the pupils of birds than 

 the natural muscarin. This difference must undoubtedly be ascribed 

 to difference in stereochemical structure, as in the case of active and 

 inactive lactic acids, and of atropin. Furthermore, Bode's iso- 

 muscarin possesses likewise an entirely different action, differing only 

 in the position of the hydroxyl group. The same is true of betain 

 aldehyd, which differs from muscarin by the elements of water. 



Mydatoxin, CjHjjNOj. — This base was obtained by Brieger in 

 1886 (III., 25, 32) from several hundred pounds of human internal 

 organs which were allowed to stand in closed but spacious wooden 

 barrels for four months, at a temperature varying from — 9° to -|- 5°. 

 He obtained much larger quantities of it, however, from horse-flesh 

 which had putrefied under the same conditions. In the process of 

 extraction it is found in the mercuric chlorid precipitate together 

 with cadaverin, putrescin and another base, CyHj^NO^. It can be 

 isolated from this mixture by recrystallizing the mercury salts, which 

 removes the cadaverin because of its difficult solubility in water, 

 and decomposing the soluble mercury salts by hydrogen sulphid. 

 The filtrate freed from mercury is now evaporated to dryness and 

 the residue repeatedly extracted with absolute alcohol, in order to 

 remove the putrescin hydrochlorid which is insoluble. The alco- 

 holic solution, after standing some time to permit complete separation 

 of any dissolved putrescin, is then evaporated to dryness and taken 

 up with water. This solution gives, on the addition of gold chlorid, 

 a precipitate of the aurochlorid of the base CyH,;^^©^. The filtrate 

 from this precipitate, containing the mydatoxin, is treated with 

 hydrogen sulphid to remove the gold, and then evaporated to dry- 

 ness. The colorless, syrupy hydrochlorid thus obtained forms with 

 platinum chlorid a double salt which is readily soluble in water, and 



