60 CHEMICAL CONSTITUENTS OF BODY AND FOOD. 



Neuridine (C 5 H 14 N 2 ) is a constant product of putrefaction of proteids. It 

 is broken up by sodium hydrate into dimethylamine and trimethylamine 

 (Brieger). Isomeric with this, though differing from it in the solubility of its 

 salts, is saprine. 



Cadaverine, a third isomeride, belongs to the diamine group, and in consti- 

 tution is pentamethylenediamine (Ladenberg). 1 



Putrescine (C 4 H 12 N 2 ) is also a diamine, being tetramethylenediamine. It 

 usually accompanies cadaverine, but as a rule makes its appearance later.-' 



All the above are free from oxygen ; the remainder are oxygenated. 



Neurine (C 5 H 13 NO) and choline (C 5 H 15 N0 2 ) are constant products of 

 cadaveric putrefaction, and their constitution has been described on p. 21. 

 They are toxic, and derive additional interest from their close relationship to 

 muscarine (C 5 H 13 N0 2 ), the alkaloid of the poisonous mushroom, Agaricus 

 muscarius? Muscarine was discovered by Schmiedeberg and Koppe. 4 

 Schmiedeberg and Harnack 5 obtained it also by oxidising choline with nitric 

 acid. Brieger found it in putrid fish, and it occurs in several vegetables. 6 



The natural alkaloid is probably not identical, but isomeric with that 

 prepared by the oxidation of choline ; 7 more recently an alkaloid, with all the 

 properties of the muscarine of plants, has been prepared artificially from rnono- 

 chloracetal and trimethylamine. 8 The constitutional formula of muscarine 



JQ 



(CH 3 ) 3 



CH 2 -C^ 



OH 



and it is the aldehyde of the non-toxic betaine (trimethylglycocine). 9 



Choline, neurine, and muscarine are all toxic ; and are antagonistic to 

 atropine, so far as relates to their action on the heart and glandular system. 10 



Gadinine (C 7 H 16 X0 2 ) is a less toxic alkaloid, which is mixed with the 

 muscarine obtained by Brieger from putrefying cod-fish. 



Mytilotoxine (C )3 H 15 N0 2 ) is the active agent in mussel poisoning. 



Typlwtoxine (C 7 H 1V N0 2 ) is obtained from cultures of the typhoid bacillus, 

 and was regarded by Brieger as the chemical poison in typhoid fever. 



Tetanine (C 13 H 22 ]S~ 2 4 ) is, or was supposed to be, the toxin in cases of 

 tetanus (Brieger). 



Gautier completes his list of animal alkaloids by including a number of 

 substances of the* uric acid group (adenine, guanine, xanthine, hypoxanthine, 

 etc.), and of the creatinine group (creatinine itself, and certain sub- 

 stances separated from muscle, which are termed xanthocreatinine, C 5 H 10 N 4 0, 



1 Ber. d. deutseh. chem. GeseUsch., Berlin, Bd. xix. S. 2585. 



2 Brieger, Berl. klin. Wchnschr., 1887, No. 44 ; Boeklisch, Ber. d. deutseh. chem. 

 GeseUsch., Berlin, Bd. xx. S. 1441 ; Baumann and Udranszky, ibid., Bd. xxi. S. 2938 ; 

 Ztschr. f. physiol. Chem., Strassburg, Bd. xiii. S. 562; Brieger and Stadthacen, Virchow's 

 Archiv, Bd. cxv. Heft 3. 



3 The Agaricus muscarius also contains a considerable amount of a non-toxic alkaloid, 

 amanitine, Nemneister, "Physiol. Chem.,"Pd. i. S. 71. 4 " Das Muscarin," Leipzig, 1869. 



5 Arch.f. exper. Path. u. PharmaJcoL, Leipzig, 1876, Bd. vi. S. 101. 



6 Such as Beta vulgaris, and the seeds of vetches and cotton. E. Schulze, Ztschr. f. 

 physiol. Chem., Strassburg, 1891, Bd. xv. S. 140; and 1892, Bd. xvi. S. 205. 



c? Boehm, Arch. f. exper. Path. u. PharmaJcoL, Leipzig, 1885, Bd. xix. S. 87. 



8 Berlinerblau, Ber. d. deutseh. chem. GeseUsch., Berlin, 1884, Bd. xvii. S. 1139. 



9 Found in Beta vulgaris; betaine has been also synthetically prepared from mono- 

 chloracetic acid and trimethylamine : 



f(CH s ) a 



CHoCl.COOH + N(CH 3 ) 3 + H = N \ CH COOH + HC1. 



tOH" 



10 The fall of blood pressure produced by choline and neurine is of cardiac origin 

 (Mott and Halliburton, " Proc. Physiol. Soc.," Feb. 1897, p. xviii., in Journ. Physiol., 

 Cambridge and London, vol. xxi.). 



