520 POISONS : THEIR EFFECTS AND DETECTION. [§ 678. 
chloroform and alcoholic potash, yield the peculiarly offensive-smelling 
carbylamine or isonitrile (Hofmann’s test), 
NH 2 (CH 3 ) + CHCI 3 +3K0H = C=eN v —CH 3 +3KC1+3H 2 0. 
Again, the primary bases, when treated with corrosive sublimate and 
carbon disulphide, evolve sulphuretted hydrogen, and mustard oil is 
produced, e.g., 
NH 2 (C 2 H 5 ) + CS 2 = CSZIN—C 2 H 5 + H 2 S. 
Ethylamine. Ethylmustard oil. 
Where a sufficient quantity of an amine is obtained, the primary, 
secondary, or tertiary character of the amine may be deduced with 
certainty by treating it with methyl or ethyl iodide. 
A molecule of the base is digested with a molecule of methyl iodide 
and distilled with potash ; the distillate is in the same manner again 
treated with methyl iodide and again distilled ; and the process is 
repeated until an ammonium base is obtained, which will take up no 
more iodide. If three methyl groups were in this way introduced, the 
original substance was primary ; if two, secondary ; if one, tertiary. 
The quaternary bases, such as tetraethyl ammonium oxhydrate, de¬ 
compose, on heating, into triethylamine and ethylene ; the corresponding 
methyl compound in like manner yields trimethylamine and methyl- 
alcohol. 
On the other hand, the primary, secondary, and tertiary bases do not 
decompose on heating, but volatilise without decomposition. 
The chief distinctions between these various amines are conveniently 
put into a tabular form as follows :— 
Primary, 
NH 2 R, 
Secondary, 
nhr 2 . 
Tertiary, 
nr 3 . 
Quaternary, 
NR 4 (OH). 
On treating with 
methyl iodide it takes 
up the following 
number of methyl 
groups 
3 
2 
1 
• • 
Reaction with nitrous 
acid 
Decomposes 
Formation of 
• • 
• •- 
Mustard oil, etc., on 
treatment with CS 2 
and sublimate 
with evolu¬ 
tion of nitro¬ 
gen gas. 
Mustard oil 
nitrosa- 
mine. 
• • 
• • 
• • 
Chloroform and alco¬ 
holic potash . 
formed. 
Formation of 
• • 
• • 
Effect of strong heat. 
c a r b y 1- 
amine. 
Sublimes. 
Sublimes. 
Sublimes. 
Decomposes. 
On addition of acids . 
Combines to 
Combines to 
Combines to 
• • 
form salts. 
form salts. 
form salts. 
