Page 39 - Academic Press Encyclopedia of Physical Science and Technology 3rd Organic Chemistry

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478 Alkaloids

arbitrary, and the boundary line is drawn in different In medieval Italy, extract of the deadly nightshade (At-
positions by different authors. ropa belladonna) was once used to make women appear
more beautiful (Italian: bella donna) by dilating the pupils
of the eyes. Since prehistory, poisoned arrows and darts
I. ALKALOIDS IN HISTORY
have been used to enhance the effect of a shot. The ancient
Greek word toxon means “bow and arrow,” and the Latin
Among the most notorious poisons in the history of
word toxicum for the poison used on arrows demonstrates
civilization are the alkaloids. Very early in history, hu-
the wide use of poisons in ancient times, for both war
man beings learned to exploit these organic compounds
and hunting. In many regions of the world (East and West
for different purposes such as therapeutic treatment, de-
Africa, South America, southern Asia, Borneo, Java), ex-
fense, cosmetics, and getting food. They also used alka-
tracts of alkaloid-containing plants were prepared to ob-
loids to murder disagreeable fellow beings. Because they
tain the poison. In the northern part of South America,
were not aware of the toxic effects of some special alka-
especially the upper basins of the Amazon and Orinoco
loids, the use of these compounds led to small and great
rivers, the arrow poison (calabash and tubo curare) pre-
disasters.
pared from different species of the genus Strychnos caused
During the course of civilization, knowledge of natural
respiratory arrest.
plant poisons and, accordingly, knowledge of poisonous
Another historical aspect of alkaloid use involves ex-
plants was lost, especially in towns, which is documented
ecution. For example, in 399 BC the Greek philosopher
by the increasing number of modern cases of poisoning.
Socrates was sentenced to die by drinking a cup of hem-
The use of alkaloid-containing plants or plant parts with
lock (a liquid extract of the poisonous plant Conium mac-
therapeutic or stimulating effects is mentioned in the old-
ulatum). This was a common sentence at the time.
est written documents. About 2700 BC, the Chinese Shen
The biological effect of alkaloids also played a ma-
Lung described the drug ma huang and its use in medicine.
jor role in the so-called Opium War (1840–1842). The
The active component of this drug prepared from the plant
Ephedra chinensis is the alkaloid ephedrine. In the “Pa- British East India Company cultivated and monopolized
opium preparation from P. somniferum in Bengal (India),
pyrus Ebers” (1600 BC, Egypt), among the more than
and, since 1773, this company had exported an increasing
80 medicinal plants or drugs described are the follow-
amount of the drug to China. The importation of opium
ing alkaloid-containing drugs: hemlock (Conium macu-
was forbidden in 1820 by the Chinese government. This
latum), opium (from Papaver somniferum), Ricinus, and
act precipitated the Opium War in 1840. China was van-
Strychnos. The European discovery of America made
quished by England and, as a consequence, Hong Kong
native American medicinal knowledge available in Eu-
wasannexedtoEngland(TreatyofNanjing).Furthermore,
rope and Asia. Drugs such as ipecacuanha (Psychotria
China was forced to open its ports to Western European
ipecacuanha) and the Peruvian bark of Cinchona spp.
nations and to the British opium trade.
stimulated medical interest because of their potent phar-
Until the 19th century, an epidemic disease caused by
macological activities. At about the same time, Europe
bread poisoning was known in Western, Central, and East-
became familiar with tabacco (Nicotiana tabacum). In
ern Europe. It was called raphania or St. Anthony’s fire.
the 17th and 18th centuries, symptoms of diseases such
Its spread between the ninth and thirteenth centuries in
as fever (Peruvian bark), pain (opium), and constipation
France and Central Europe reached dramatic proportions
(Ricinus) were treated with plant products. Even diarrhea
since, especially for poor people, no substitute for the sta-
(ipecacuanha) and malaria (Peruvian bark) became cur-
ple food, corn, existed. Today, we know that alkaloids of
able. Tobacco and ephedra (against sleep) were used as
the fungus Claviceps purpurea were responsible for these
stimulants.
pharmacological effects. The fungus grows mainly on rye
Even in ancient times alkaloid-containing drugs such
and barley and sometimes on wheat and wild-growing
as opium, mandragora (Mandragora officinalis), and hen
grass, producing several alkaloids, the so-called ergot al-
bane (Hyoscyamus niger) were used as anodynes in op-
kaloids, which contaminate the food by way of the flour.
erations. Synthetic chemicals such as narcotics were not
Consuming the poisoned food led to this disease, to multi-
introduced until the 19th century.
lations, and in many cases to death. Nevertheless, ergot has
Some of the drugs that were well known in the past are
been used in medicine for many centuries (1582, herbal
today being misused and abused and their use is there-
book of Lonizer) to enhance labor in women.
fore restricted. They are prepared mainly from alkaloid-
containing plants, for example, opium and morphine from
Papaver somniferum, cocaine from Erythroxylum coca, II. HISTORY OF ALKALOIDS
and mescaline from Lophophora williamsii. Repeated
consumption of these drugs leads to mania and addiction The year 1817 is regarded as the birth of alkaloid chem-
(morphinism, cocainism, etc.). istry. In this year, the German pharmaceutical chemist