362 POISONS : THEIR EFFECTS AND DETECTION. [§ 429. 
Alypin, C 16 H 26 N 2 0 2 .HC1, is the hydrochloride of benzoyl-1, 3-tetra- 
methyl-diamino-2-ethy 1-isopropanol, 
C 2 H 5 
N(CH 3 ) 2 .CH 2 .C.O(C 6 H 5 CO)< N(CH 3 ) 2 .HC1. 
x ch 2 
A white, hygroscopic, crystalline powder; m.p. about 170° ; numbs the 
tongue like cocaine ; the picrate melts at 195°-197°. An aqueous solu¬ 
tion of alypin gives a strong white precipitate with potassium iodide 
solution (stovaine and cocaine give no precipitate). Similarly, alypin 
can be distinguished from the above by giving a crystalline precipitate 
with potassium bichromate soluble in HC1. 
Stovaine. — Dimethyl-amino, dimethyl-ethyl-carbinol benzoate (ben- 
zoy 1-ethyl-dimethyl-amino-propanol hydrochloride), 
C 14 H 21 N0 2 .HC1 = HC1.N(CH 3 ) 2 CH 2 .C 2 H 5 C.(0 6 H 5 C0).CH 3 . 
The free base is an oil, soluble in ether, alcohol, and other solvents, with 
a faint, unpleasant odour; boiling-point about 201°. Stovaine is the 
crystalline hydrochloride, which is almost insoluble in ether. The base 
is easily extracted by ether from an alkaline liquid ; the hydrochloride 
can be precipitated from the ethereal solution by passing bubbles of dry 
hydrochloric acid gas into the volatile solution. An aqueous solution of 
stovaine is slightly acid. The taste is a little bitter, and produces similar 
numbness in the tongue to cocaine, when tested in the manner described 
(p. 357); it also produces slight dilatation of the pupil and disturbance 
of power of accommodation. 1 or 2 mgrrns. dissolved in 4 drops of con¬ 
centrated sulphuric acid and then made alkaline by potash, and heated 
on the water-bath, develop the odour of ethyl benzoate. Instead of sul¬ 
phuric acid, Ternic 1 breaks up the molecule by 1 c.c. of a mixture of 
nitric and hydrochloric acids, and heats on the water-bath until the acids 
are driven off, and then adds 1 c.c. of alcoholic potash. Other reactions 
are similar to those of cocaine, but it can be distinguished from alypin 
by the addition of a few drops of 5 per cent, potassium bichromate : 
alypin gives a yellow crystalline precipitate, stovaine no change'. The 
picrate melts at from 114-5° to 116-5°. Miilliken 2 directs the picrate to 
be prepared as follows : — Dissolve -05 stovaine in 7 c.c. water, add 3 c.c. 
of saturated aqueous solution of picric acid. Heat to boiling; cool 
slowly, fdter, wash crystals on filter with 2 c.c. of cold water, recrystallise 
from 12 c.c. boiling water, allow to stand for some hours, filter off the 
fine yellow-tinted crystals of the picrate, and wash with 1 c.c. of water. 
Dry at 100° for fifteen minutes. 
The reactions of these derivatives with salts of gold, platinum, 
and permanganate are summarised in the following table : — 
1 Apotheker-Ztg., 1905 . 
2 Op. cit. 
