i8 
LIVING PROTOPLASM AND 
diamid sulfate will kill a rabbit in ij hour (Buchner). 
Why is it then,—it will be asked that hydroxylamin and 
diamid are such strong poisons compared with ammonia ? The 
answer can only be found in the marked difference of behaviour 
to aldehydes (resp. Ketons). It has been demonstrated by 
recent investigations, that salts of hydroxylamin and of diamid 
(hydrazin) act even in high dilutions upon aldehydes while 
ammonia acts only as free base or as carbonate and with less 
energy. This difference is due to the greater lability of the 
hydrogenatoms in the former, attacking thus easier the labil 
oxygen of aldehydes and ketons. 
>H 
N—h 
Ammonia. 
N—H 
\ OH 
Hydroxylamin. 
,H 
N—H 
' nh 2 
Diamid. 
We find analogous differences of intensity of toxicological 
actions between anilin C 6 H 5 .NH 2 and phenylhydrazin, C 6 H 5 . 
NH.NH,; between pyridin C 5 H 5 N and piperidin C 5 H I0 .NH ; 
between phenol and amidophenol, which latter is,-in accordance 
with the behaviour to aldehydes,- also a stronger poison than 
anilin.— 
The reaction between hydroxylamin and an aldehyde is 
expressed by the following equation : 
M-CÜh +H 2 N-OH = (x) — C—h~ 0H + H 2 0 
- A -X - A _- ■_ 
An aldehyde. An aldoxim. 
It is of considerable interest, that also certain derivatives 
of hydroxylamin react easily with aldehydes and exhibit in ac¬ 
cordance therewith a poisonous character; these derivatives are 
the “ amidoxims,” prepared by Tiemann by the action of con¬ 
centrated hydroxylamin upon nitriles at higher temperatures : 
(*)-C=N+H 2 N-OH = (*) —CIn-oh 
A nitril. An amidoxim. 
t \ NH 2 i/\ /"\ — G 
(x) — C = N _01I + (y) — C_H 
W-C = n-oh W + H 2 0‘) 
An aldehyde. 
1) The product thus formed can undergo an atomic migration; Tiemann, 
Ber. 22, p. 3124. 
