308 CBEMISTBT OF TEE PTOMAINS. 



a base possessiug an antagonistic action to muscariu. Kobert be- 

 lieved that this " fungus-atropin " existed in the fresh mushrooms, 

 and showed that Kussula emetica contained this compound as well as 

 cholin and muscarin. 



This base is especially interesting because of the relation it bears 

 to cholin, for Schmiedeberg and Harnack showed that it is formed 

 when cholin, or, better still, the platinochlorid, is oxidized by 

 concentrated nitric acid. Nothnagel by the action of concentrated 

 nitric acid on cholin obtained muscarin, also a nitroso derivative 

 (nitric acid and cholin ether), and a substance which is the chief 

 product, besides a little muscarin and the nitroso compound, when 

 the oxidation is carried out with dilute nitric acid. The muscarin 

 from cholin does not combine with phenyl-hydrazin ; betain alde- 

 hyde does. The chlorid on treatment with acetic anhydrid or ben- 

 zoyl chlorid yields an anhydrid of muscarin (Nothnagel), the exact 



composition of which is yet undetermined ; the group — CH<^j-jtt in 



muscarin is probably changed into an aldehyde group — COH. 



In the preparations of muscarin from cholin a small quantity of 

 a nitroso compound forms, the platinum salt of which resembles that 

 of muscarin in solubility, but never in form, which is always plu- 

 mose. These crystals are permanent in the air and contain two 

 molecules of water which are not driven off at 100°. They melt 

 at 223°- 224° with decomposition. It possesses the formula : 



(Cl.N(CH,),.CH,.CH,0.N0),.PtCl4 + 2H,0. 



The gold salt forms fine, light-yellow needles which are anhydrous 

 and melt at 240°. It gives Liebermann's nitroso reaction — blue 

 color with phenol and sulphuric acid. 



In addition to the natural and synthetic bases a third " muscarin," 

 OH.N(CH3)3.CH2.COH, was prepared by Berlinerblau by the action 

 of baryta on trimethylamin and chloracetal. Fischer prepared the 

 same compound, by the action of concentrated hydrochloric acid on 

 acetal-trimethyl ammonium hydroxid. This base, however, difFers 

 from muscarin by the elements of water — anhydro-muscarin. In 

 reaKty it is betain aldehyde, since on oxidation with moist silver 

 oxid it yields betain (Fischer). Unlike real muscarin, it has -no 

 action on the heart of frogs or on the pupils of birds (Meyer). Like 

 most ammonium bases it induces strong salivation and perspiration. 

 Schmiedeberg found it to resemble cholin in its action, whereas 

 Luchsinger found it tp agree in this respect with muscarin. 



A fourth base, oxycholin— OH.N(CH3)3.CH.OH.CH20H, was 

 prepared by Bode by the action of silver oxid on hypochlorous acid 

 and neurin chlorid. Its platinum salt melts at 254° (Nothnagel). 

 Its physiological action is different from that of muscarin. Thus, 

 n frogs it slows the heart, but does not cause stoppage. Atropin 



