314 CHEMISTRY OF THE PT0MAIN8. 



The hydrochlorid, CgHjjNOjj.HCl, prepared from the aurochlorid, 

 crystallizes in tetrahedra. It is extremely poisonous, and according 

 to Brieger produces exactly the same symptoms which have been ob- 

 served by Schmidtmann in persons who have partaken of poisonous 

 mussels (see page 190). On standing, however, the pure hydrochlorid 

 gradually becomes dark and decomposes with loss of ite poisonous 

 property — a change corresponding to that which tetanin undergoes 

 (p. 322). The gold salt is better adapted for preservation. The 

 ordinary alkaloidal reagents produce in its solutions, if at all, only 

 oily precipitates. 



The aurochlorid, CgH„N02.HCl.AuClj (Au = 41.66 per cent.), 

 crystallizes in cubes. Its melting point is 182°. 



It is well to observe that Brieger was unable to obtain this base 

 from mussels that were allowed to putrefy for sixteen days. 



As stated under mydatoxin, the formula of the hydrochlorid, 

 CgH^N02.HCl, is applicable to either one of the two bases, CjEEj, 

 NOj-OH or CgHjjNOj . The base corresponding to the first formula 

 is evidently a homologue of muscarin, and should possess a similar 

 physiological action. As a matter of fact, mytilotoxin does resemble 

 muscarin somewhat in this respect, and its occurrence together with 

 betain would seem to make it a decomposition product of lecithin, in 

 which case this base must be looked upon as a member of the cholin 

 group. A compound corresponding to the formula CgHj^NO^OH 

 was prepared by Hanriot in a manner analogous to Wurtz's synthesis 

 of cholin, by treating glycerin monochlorhydrin with trimethylamin. 

 This base, trimethyl-glyceryl ammonium hydrate, has the structure : 



CH,.CHOHCH,OH 

 N(CH.),OH. 



It was suggested that Hanriot's base might possibly be identical 

 with mytilotoxin, but a careful comparison made by Brieger showed 

 that it possesses no physiological action and that its chemical prop- 

 erties are entirely different. 



Mytilotoxin would, therefore, seem to possess the formula CgHj, 

 NOj, as originally given by Brieger. From the fact that on distilla- 

 tion with potassium hydrate it yields trimethylamin, it follows that 

 mytilotoxin is a quaternary base. He is incUned to regard it as a 

 methyl derivative of betain, which is so common in mussels, and 

 represents it by formula No. 1. 



(1) (2) 



CO,H CO.H 



CH.CH, CH.CH, 



ij(CH,),.OH i(CH,),.OH 



