Personnel in the second world war.

Even higher levels of alkaloids and higher proportions

of hircine can be obtained from selected D myoparaides x D leichhardtii hybrids, wich are
currently cultivated. The hybrid is superior to either parent, and can yield 1-2.5% hyoscine
and 0-1% hyoscyamine. Duboisia leaf is an important commercial source of medicinal
tropane alkaloids.
The third species of Duboisia, D. hopwoodi, contains little tropane alkaloid content, but
produces mainly nicotine and related alkaloids, e.g. nor nicotine (see page 290). Leaves of
this plant were chewed by aborigines for their stimulating effects.
Allied Drugs
Tropane alkaloids, principally hyscyamine and hyoscine, are also found in two other
medicinal plants, scopolia and mandrake, but these plants find little current use. Scopolia
(scopolia carniolica; solanaceae) resembies belladonna in appearance, thougt it is
considerably smaller. Both root and leaf inaterials have been employed medicinally. The
European mandrake (man-dragora officinarum; solanaceae) hasa complex history as a
hypnotic, a general panacea, and an aphorodisiac. Its collection has been surrounded by
much folklore and superstition, in that pulling it from the ground was said to drive its
collector mad due to the unearthly shrieks emitted. The roots are frequently forked and are
loosely likened to a man or woman. Despite the doctrine of signatures, wich teaches that
the appearance of an object indicates its special properties, from a pharmacological point of
view, this plant would be much more efficient as a pain reliever than as an aphrodisiac.
Hyoscyamine, Hyoscine and Atropine
All the above solanaceous plants contain as main alkaloidal constituents the tropane esters
(-) hyoscyamine and (-) hyoscine, together with other minor tropane alkaloids. The
piperidine ring in the bicyclic tropane system has has a chair-like conformation, and there is
a ready inversion of configuration at the nitrogen atom so that the N-methyl group cn
equilibrate between equatorial and axial positions (Figure 6.6). An equatorial methyl is
storongly favoured provided there are no substituents on the two-carbon bridge, in wich
case the axial form may predominate. (-)-Hyoscyamine is the ester of tropine (Figure 6.4)
with (-). (S) tropic acid. The optical activity of both hyoscyamine and hyoscine stems from
the chiral centre in the acid portion, (S)-tropic acid. Tropine itself, although containing
chiral centres, is a symmetrical molecule and is optically inactive. Le. It can be regarded as
a meso isomer. The chiral centre in the topic acid portion is adjacent to a carbonyl and the
aromatic ring, and racemization can be achieved under mild conditions by heating or
treating with base. This will involve an intermediate enol (er enolate) which is additionally.