Scientific American Supplement, No. 324, March 18, 1882Various
Science
Scientific American Supplement, No. 324, March 18, 1882
Various
Science -- Periodicals
ON THE MYDRIATIC ALKALOIDS.
By ALBERT LADENBURG.
We translate the following important article, says the _Chemists'
Journal_, from the _Moniteur Scientifique_ of last month. It may be
explained for the sake of our student readers that the word _mydriatic_
is derived from the Greek _mudriasis_, which means paralysis of the
pupil.
The synthetical researches which I have undertaken with a view to
explain the constitution of atropine have shown me the necessity of
studying the connection of atropine with the other alkaloids, which have
an analogous physiological action. According to the early researches we
could not discover any of these relationships which only become evident
when we come to study the new discoveries which have been made in
connection with the tropines, to which class belong both duboisine
and hyoscyamine, which, although differing from atropine, are equally
mydriatic in their action.
I.--ATROPINE.
Discovered by Mein in 1831 in the roots of belladonna. More thoroughly
studied some time after by Geiger and Hesse, who confirmed Mein's
results. Liebig next published an analysis of the alkaloid, which was
afterward shown to be incorrect. He consequently modified his
formula, and gave the following as the composition of atropine;
C_{17}H_{23}NO_{3}. Liebig's amended analysis was afterward confirmed by
Planta, who further showed that the alkaloid itself melted at 194° F.,
and its double gold salt at 275° F. It is worthy of remark that the
first figure was considered correct until my researches proved the
contrary. The physiological action of atropine, especially in relation
to the eye, has been most carefully studied by several celebrated
ophthalmologists, such as Graef, Donders, Bezold, and Bloebaum. Its
chemical properties have also been the object of very extensive
researches by Pfeiffer, Kraut, and Lassen. Pfeiffer first discovered
that benzoic acid was one of the products of decomposition of atropine,
and Kraut split atropine by means of baryta water into atropic
acid, C_{9}H_{6}O_{2}, and tropine, C_{8}O_{15}NO. Lassen, who used
hydrochloric acid, discovered the true products of the splitting up of
atropine, viz., tropic acid, C_{9}H_{8}O_{3}, and tropine, C_{8}H_{15}N,
and proved at the same time that atropic acid is easily formed by the
action of boiling baryta water on tropic acid, while hydrochloric acid
at all temperatures forms isatropic acid, an isomer of atropic acid.
Kraut confirmed these results, and showed that atropic acid as well as
cinnamic acid gives benzoic acid by oxidation, and hydratropic acid (the
isomer of phenylpropionic acid) by reduction with sodium amalgam. These
results are sufficient to show that tropic acid may have one of the
following two formulae.
I II
CH_{2}OH CH_{3}
/ /
C_{4}H_{5}CH or C_{8}H_{5}--C--OH
\ \
OOHO COOH
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