Indole Alkaloids - History

History

The action of some indole alkaloids has been known for ages. Aztecs used the psilocybin mushrooms which contain alkaloids psilocybin and psilocin. The flowering plant Rauwolfia serpentina which contains reserpine was a common medicine in India around 1000 BC. Africans used the roots of the perennial rainforest shrub Iboga, which contain ibogaine, as a stimulant. An infusion of Calabar bean seeds was given to people accused of crime in Nigeria: its rejection by stomach was regarded as a sign of innocence, otherwise, the person was killed via the action of physostigmine, which is present in the plant and which causes paralysis of the heart and lungs.

Consumption of rye and related cereals contaminated with the fungus Claviceps purpurea causes ergot poisoning and ergotism in humans and other mammals. The relationship between ergot and ergotism was established only in 1717, and the alkaloid ergotamine, one of the main active ingredients of ergot, was isolated in 1918.

The first indole alkaloid, strychnine, was isolated by Pierre Joseph Pelletier and Joseph Bienaimé Caventou in 1818 from the plants of the Strychnos genus. The correct structural formula of strychnine was determined only in 1947, although the presence of strychnine in the structure of the indole nucleus was established somewhat earlier. Indole itself was first obtained by Adolf von Baeyer in 1866 while decomposing Indigo.

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