THE PHARMACEUTICAL JOURNAL AND TRANSACTIONS. 
[October 15,187&. 
301 
bably formed under similar circumstances to the terpine 
camphors, i. e. hy oxidation, or the assimilation of the 
elements of water. I have failed, however, in forming 
this substance artificially hy oxidizing the resin spirit 
with nitric acid.* 
It is not present in newly-prepared resin spirit, as I 
have already explained; and as my supply of colophonic 
hydrate was expended, my researches upon this substance 
were, I am sorry to say, brought to a close. It is, how¬ 
ever, my intention to renew them at a future period.— 
The Chicago Pharmacist. 
HYOSCYAMIN; ITS PREPARATION AND CONSTI¬ 
TUTION, WITH REMARKS ON SOME OTHER 
SUBSTANCES PRESENT IN HENBANE SEEDS. 
BY HEINRICH HOIIN. 
Assistant at the Jena Institute of Pharmaceutical 
Chemistry. 
At the suggestion of Professor Ludwig, the author 
undertook the preparation of a large quantity of hyoscy- 
amin, with the object of studying its characters, and en¬ 
deavouring to determine its formula. 
The material used for the purpose was the seed of 
Uyoscyamus niger , furnished by Herr A. Geheeb, in Geisa. 
Separation of Uyoscyamin. —5450 grm. of the fresh seed 
was dried and coarsely powdered, then extracted with 
alcohol (containing 90 per cent, by volume) in two suc¬ 
cessive operations. The tinctures thus obtained were 
operated upon separately. 
After distilling off the alcohol from the first tincture, 
there was deposited a considerable quantity of yellowish- 
brown resin, while the remaining residue, which had an 
acid reaction, separated after some time into a watery 
layer, and an oily layer floating above. During the 
cooling of the liquid residue, more of the yellowish- 
brown resin separated, and this was set aside with the 
other portion for subsequent examination. The oil was 
separated and washed three times with hot water; its 
perfect separation from tho aqueous emulsion required 
long- rest on the water bath, and meanwhile more resin 
was deposited. The resin was nitrogenous. 
The whole of the aqueous liquid was then evaporated 
to about 500 grm. filtered through paper moistened with 
water, the filtrate rendered alkaline with caustic potash, 
and then shaken with about \ lb. of chloroform. The 
chloroform was then well washed with water and dis¬ 
tilled off, leaving about 1 grm. of slightly coloured alka¬ 
loid of a tough consistence and strong unpleasant odour. 
This substance presented all the characters of hyoscya- 
min described by Geiger. It had a tolerably strong and 
permanent alkaline reaction, was precipitated by iodine 
water of a brown colour, by chloride of gold, in yellow 
flocks that became crystalline after a time, by tannin and 
chloride of mercury in white flocks, and by caustic potash 
from a concentrated solution, the precipitate being so¬ 
luble in excess of the alkali. 
A solution of the alkaloid in very dilute alcohol left 
for evaporation over sulphuric acid, presented on the 
second, day flocculent deposits, which were found under 
the microscope to be well-developed stellate groups of 
needles. But since these crystals were still yellow-co¬ 
loured, and mixed with a viscid substance, they were 
again dissolved in chloroform, the solution shaken with 
hydrochloric acid, and the alkaloid again taken up with 
chloroform after the aqueous solution had been rendered 
alkaline with carbonate of potash. After evaporating off 
the chloroform, there remained only about 0'5 grm. of 
* Mr. Turner forwarded me from England a bottle con¬ 
taining resin spirit, in which he had observed crystals. 
Thev proved on examination to be colophonic hydrate. The 
bottle originally contained about 8 oz.; but from evaporation, 
only half an ounce remained; it consisted of about 25 per 
cent, of colophonic hydrate. It had been exposed to sunlight 
for about eight years; fight, however, is not essential to the 
formation of this compound. 
slightly yellow alkaloid, but this could not be crystal¬ 
lized, and even when converted into hydxochlorate, the 
salt could not be crystallized. 
The chloroform that was used for purification, and had 
been shaken with dilute hydrochloric acid, gave on eva¬ 
poration a white waxy residue, crystallizing in groups of 
whito needles. 
The alkaline liquid that had been shaken with chloro¬ 
form was slightly acidulated with hydrochloric acid, and 
a quantity of dark coloured flocks separated, while an 
odour of butyric acid became sensible. On adding to> 
the filtered liquid a concentrated solution of tannic acid, 
a yellowish-white precipitate was formed; this was col¬ 
lected on a filter, washed with cold water, dissolved in 
dilute alcohol, then mixed with fresh precipitated car¬ 
bonate of lead, and evaporated to dryness. The residual 
mass was finely powdered, boiled several times with 
strong alcohol, and the filtered solution distilled. When 
the liquid was reduced to a certain volume, there were 
formed small white crystals in the retort; the quantity, 
however, was too small for collecting, and the whole 
liquid was evaporated slowly in a capsule, but no sign of 
crystallization was recognizable, the residue being a 
tough yellowish mass, of bitter taste, no particular smell, 
and readily soluble in water or alcohol. 
The presence of butyric acid was ascertained, also of 
volatile bases, and of a glucoside, to which the author 
gives the name Hyoscypikrin. 
The second alcoholic tincture was treated in the same 
manner and with the same result as before. 
The circumstance that the fat oil obtained from the 
tincture was acid, induced the author to examine this oil 
for alkaloid, and ho found that it contained a consider¬ 
able quantity of hyoscyamin. However, this could not 
be crystallized either from alcohol or benzol, but in all 
instances tho solution, when reduced to a small bulk, be¬ 
came gelatinous, and, when dried up, left a shining 
gummy residue. 
In order to exhaust tho seed completely, it was finally 
digested with water, containing about 1 per cent, sul¬ 
phuric acid. The expressed and filtered liquid was neu¬ 
tralized with ammonia evaporated to a syrup, during 
which operation much grey slimy substance separated 
the thickened liquid was digested with acidified alco¬ 
hol, the solution neutralized and evaporated; the dark 
brown residue mixed with ammonia was shaken with 
chloroform, and gave off a further quantity of hyoscya¬ 
min. 
The entire quantity of alkaloid obtained from the seed 
was about 3 grams or 0 - 06 per cent., which is more than 
was obtained by Renard. 
The author suggests that since the oil takes up hyoscya¬ 
min, it would be desirable in preparing the alkaloid to- 
extract the oil first by means of bisulphide of carbon or 
some such solvent. 
Another difficulty arises from the chloroform remaining 
mixed in the state of emulsion with the liquids, when it is 
shaken with them, rendering the operation very tedious. 
This is best got over by evaporating the liquids to a 
syrupy consistence and extracting with strong alcohol to 
separate mucilage, dextrin, etc. 
The precipitation of hyoscyamin by chloride of plati¬ 
num has been confirmed by the author; but it takes- 
place only from concentrated solutions, and the pre¬ 
cipitate is redissolved by excess of the chloride of pla¬ 
tinum. He had also occasion to observe the strong 
action of hyoscyamin in dilating the pupil, in conso- 
quence of a dilute solution being accidentally spirted into 
one of his eyes; about a quarter of an hour afterwards 
considerable dilatation of the pupil took place; on the 
second day the other eye was similarly affected, and this 
lasted for three days. 
To determine the composition of hyoscyamin, a double 
salt of gold was prepared and analysed with results lead¬ 
ing to the formula:— 
C 18 H m N0 6 H Cl Au Cl 3 . 
