SPERMIN. 451 



long, sharp, plumose needles — distinction from diethylenediamin. 

 The aqueous solution of the base is precipitated by phosphomolybdic, 

 phosphotungstic and tannic acids, gold and platinum chlorids. It 

 cannot be volatilized from alkaline solution by steam without under- 

 going decomposition (Majert and Schmidt). It is not poisonous. 



The hydrochlorid, CjHjN.HCl (?), crystallizes in six-sided prisms, 

 united in tufts, and is extremely soluble in water, almost insoluble 

 in absolute alcohol and ether. 



The aurochlorid, C^HjN.HCl.AuClj (?), forms shining, golden- 

 yellow, irregular plates, and when freshly precipitated it is easily 

 soluble in water, alcohol, and ether, but the dried salt is incom- 

 pletely soluble in water. The aqueous solution, treated with mag- 

 nesia, gives off a sperm-like odor. The platinochlorid crystallizes 

 in prisms. 



The phosphate, (C^HjN)^.!!,?©^ -f- 3Hp (?), forms prisms and 

 slender double pyramids arranged in rosettes. It is difficultly sol- 

 uble in hot water, insoluble in alcohol, easily soluble in dilute acids, 

 alkalis and alkali carbonates. It melts with decomposition at about 

 170°. It is probable that the above formula does not represent the 

 salt as found, and from theoretical considerations Ladenburg is 

 inclined to think that Schreiner's phosphate has the composition 

 (C,H,NH),Ca(POJ,. 



Ladenburg and Abel prepared in 1888 a compound, ethyleneimin, 

 which was first supposed to be isomeric with spermin. The reaction 

 whereby it is prepared is similar to that by which Ladenburg 

 effected the synthesis of piperidin. Ethylenediamin hydrochlorid is 

 subjected to dry distillation, when it decomposes into ammonium 

 chlorid and the hydrochlorid of the new base. The reaction was 

 supposed to be represented by the equation : 



CHjNHj.HCl CH,v 



[ =1 >NH.HCl + NH,a. 



CH,NH,.HC1 CH/ 



Since then Ladenburg showed that the boiling point of this 

 compound did not agree with what it should be theoretically, if 

 represented by the above formula. A determination of the vapor 

 density showed that the molecular weight was twice that correspond- 

 ing to the formula given, and hence was C^Hj^Nj. Majert and 

 Schmidt assuming spermin to be ethyleneimin, as was apparently 

 shown by Ladenburg and Abel's investigation, attempted to prepare 

 the latter on a manufacturing scale with the expectation that it 

 might be used as a substitute for Brown-S6quard's testicular fluid. 

 They were soon able to show, however, that ethyleneimin did not 

 possess the composition assigned to it, but that it was identical with 

 Hofmann's diethylenediamin (piperazin, p. 418), 



HN< >NH. 



