February 22, 1373.] THE PHARMACEUTICAL JOURNAL AND TRANSACTIONS. 
6G1 
PROPYLAMINE OR TRIMETHYL AMINE. 
being represented by the formula— 
Attention has recently been directed by Dr. Sydney 
Ringer in some notes in the Medical Record , to 
the revival of the use of a compound ammonia 
as a remedy for rheumatism, and the use of the 
substance has been the subject of discussion at some 
of the French medical societies, as well as the 
Paris Societe de Pharmacie, as will be seen by the 
report at p. 070, 071. Since the first introduction of 
this remedy in 1854 by Awenarius, of St. Peters¬ 
burg, it has also been employed both in this coun¬ 
try and in America to some extent, though without 
any very decided knowledge having been acquired 
respecting its pliysiological action and medicinal 
virtues. However, its use being now a prominent 
subject of discussion, the chemical history of the 
substance has an immediate interest for the phar¬ 
macist, and this is especially the case since there is 
considerable uncertainty both as to what precise 
compound is indicated by the term propylamine, 
and also what has been used medicinally under that 
name. Some account of the substance will there¬ 
fore be useful to the readers of this Journal. 
Propylamine is a compound or substituted am¬ 
monia in which one of the three molecules of hydrogen 
belonging to ordinary ammonia is replaced by the 
radicle propyl (or trityl) C 3 H 7 , the third member 
of the ethyl series of radicles ; its constitution being 
represented by the formula— 
N 
C,H 
H 
H 
r 
It is described by Mendius, who first prepared it, as 
a very mobile, colourless liquid, possessing a strong 
ammoniacal odour, boiling at 50°, dissolving in water 
with evolution of heat, specific gravity ’7134 at 21° C. 
With acids, propylamine forms crystallizable salts, 
the sulphate being deliquescent, and the liydroclilorate 
NCgHgtlCl very deliquescent, freely soluble in al¬ 
cohol, but almost insoluble in ether. 
The method first adopted to obtain propylamine 
was the hydrogenation of ethyl cyanide or pro- 
pionitrile, a compound intermediate between the ordi¬ 
nary alcohol of the alcohol series and the pro¬ 
pionic acid of the parallel series of acids. For this 
purpose 30 parts by weight of ethyl cyanide, 500 
parts alcohol,'200 parts water, and 500 parts of a 20 p.c. 
solution of hydrochloric acid were mixed and made 
to act upon metallic zinc added in excess, the whole 
being distilled and the distillate mixed with 400 
parts more hydrochloric acid and poured back 
again upon the zinc remaining undissolved. After 
again distilling to get rid of alcohol, excess of caustic 
soda is added to the residue, and then the propyl¬ 
amine is distilled off together with water. 
Besides this normal propylamine there is another 
compound of the same composition called isopropyl¬ 
amine 
CH (CH 3 ) 2 
N H 
IH 
This boils at about 32° C. The liydroclilorate crys¬ 
tallizes in cubes, while that of the normal propyla¬ 
mine forms square plates. 
Another isomer of propylamine is trimetliylamine^ 
an ammonia in which each of the three molecules 
of hydrogen is replaced by methyl, its constitution 
Third Stries, No. 139. 
*CH 3 3 
This substance was formerly mistaken for true propy¬ 
lamine or trityl amine ; and it seems probable that in 
regard to the remedy now proposed to be used in the 
treatment of rheumatism, the same kind of confusion 
still prevails. Trimetliylamine is, however, a sub¬ 
stance very different from propylamine. It is an 
oily liquid with a strong odour of stale fish, and holla 
at 9° C. This substance was first obtained by 
Hofmann, by the action of ammonia upon methyl 
iodide. It also exists in herring brine, ergot of 
rye, and several plants, and is apparently one of 
the products of the putrefaction of nitrogenous sub¬ 
stances, such as urine, guano, dough, fish, etc. 
The directions given in Wood andBache’s United 
States Dispensatory for the preparation of propyla¬ 
mine from herring brine, on the authority of Profes¬ 
sor Procter, clearly point to trimetliylamine, and it 
was from the same source that in 1850 Wertlieim 
obtained the base to which he gave the name of 
propylamine in the first instance. It would appear, 
moreover, from the accounts given of the substance 
used under the name of propylamine that it was 
really its isomer trimetliylamine that was referred 
to. The physical characters of these two substances 
are very distinct, and the smell of even propylamine 
is said to be very different from the herring-like 
odour of trimetliylamine, so that there would not be 
much difficulty in settling this point. 
At a recent meeting of the Paris Societe de Phar¬ 
macie a committee was appointed to inquire into 
the subject, on the ground of the uncertainty attend¬ 
ing it. The price hitherto charged for the material 
in the state of aqueous solution appears to have 
been about 5s. per ounce ; but at a recent meeting of 
the Societe Medicale desHopitaux it was stated that 
it would be procurable at about one-third that cost. 
M. Adrian and M. Dassaigne recommend the use 
of an liydroclilorate of the base as being more con¬ 
venient than the solution. 
SULPHO VITIATE OF SODA. 
BY CHARLES RICE. 
Having prepared this salt some time, and having 
tried several methods for obtaining it, I can recom¬ 
mend the following, as yielding a good product at a 
moderate price : 
Take of alcohol (sp. gr. 0-815), sulphuric acid (sp. 
gr. 1-830), each 64 fl. oz. Add the acid to the alco¬ 
hol, contained in a large flask, in portions, at short 
intervals. At first the temperature of the mixture 
rapidly rises to 212° F., and violent ebullition 
takes place at each successive addition of ackff 
but this gradually ceases as the specific gravity of 
the mixture increases, and the last portions of 
the acid may be added quite rapidly. Cover it 
well, and allow it to stand for two or three days. 
The mixture of alcohol and acid should not be raised 
to the boiling point, since the yield of sulplioviuio 
acid is thereby considerably diminished, while tann 
of oil of wine, ether, etc., is proportionately inc.-easod. 
Pour the mixture slowly, while stirring, into five 
times its bulk of*water, and saturate the acid liquid 
with carbonate of lime. Strain the liquid, wash the 
