CADAVEBIN. 273 



verted cadaverin into piperidin, and found the latter base to agree 

 entirely in its chemical and physical properties with those of the 

 natural alkaloid (£«■., 19, 2586). Ladenburg, however, observed 

 one apparent difference between cadaverin and pentamethylenedi- 

 amin, and that was in the composition of the mercury double salts. 

 That of the former base, whether obtained from alcoholic or aqueous 

 solution (Bocklisch, Ber., 20, 1441), was found to combine with four 

 molecules of mercuric chlorid; whereas the double salt of penta- 

 methylenediamin was found by Ladenburg to contain only three 

 molecules of mercuric chlorid. Subsequently he found that he had 

 prepared this salt by mixing the aqueous solutions of the hydro- 

 chlorid of the base and of the mercuric chlorid in the molecular ratio 

 of 1 to 4, and on using a larger excess of mercuric chlorid he ob- 

 tained a salt containing four molecules of mercuric chlorid {Ber., 20, 

 2216). The complete identity of these two bases has, therefore, been 

 established. The constitutional formula of cadaverin is, therefore : 



NHj — CHj — CHj — CH, — CHj, — CH, — NHj • 



Cadaverin can be prepared synthetically according to Ladenburg's 

 method. For this purpose trimethylene bromid is converted into 

 the cyanid, and this is then reduced by sodium in absolute alcohol. 



Cadaverin forms a somewhat thick, water-clear, syrupy liquid, 

 which possesses an exceedingly unpleasant odor, resembling some- 

 what that of coniin (piperidin) and of semen. When dehydrated 

 with potassium hydrate it boils at 115°— 120° (Brieger). It boils 

 at 175° (Brieger, III., 98), and fumes in the air. The base eagerly 

 absorbs carbonic acid from the air, and solidifies into a crystalline 

 mass, the carbonate. It is volatile with steam, and can be distilled, 

 without decomposition, even in presence of sodium or barium hydrate 

 or soda-lime. Neuridin, its isomer, decomposes under these circum- 

 stances. When heated with alcoholic potash and chloroform it does 

 not give the isonitril reaction, nor does it give the characteristic odor 

 of oil of mustard on treatment with carbon disulphid and mercuric 

 chlorid. The absence of these reactions at first induced Brieger to 

 conclude that cadaverin and putrescin were not primary amins, but 

 Ladenburg (1885) showed that this conclusion was not justifiable. 

 These two reactions are given by primary monamins, but in this case 

 they are not given by cadaverin, a primary diamin. It is probable 

 that this behavior holds true for all diamins. 



Cadaverin is, undoubtedly, identical with the so-called " animal 

 coniin," which has been isolated at various times from cadavers. 



Cadaverin and putrescin were at first regarded as physiologically 

 indifferent, but more recent investigations by Scheurlen, Grawitz, 

 and others, show that both these bases are capable of producing strong 

 inflammation and necrosis. According to Behring, in large doses it 

 is poisonous to mice, rabbits, and guinea-pigs ; it is not poisonous to 

 18 



