Coniine is a poisonous alkaloid found in poison hemlock (Conium maculatum), the yellow pitcher plant (Sarracenia flava),, and fool's parsley (Aethusa cynapium) and contributes to hemlock's fetid smell. It disrupts the peripheral nervous system and is toxic to humans and all classes of livestock; less than 0.1g is fatal to humans, with death caused by respiratory paralysis. Notably, Socrates was sentenced to death by drinking a mixture containing poison hemlock in 399 BC.
Coniine has two stereoisomers: (S)-(+)-coniine, and (R)-(−)-coniine, both of which are present in hemlock (see "Modern Chemical Studies", below). Coniine was first synthesized by Albert Ladenburg in 1886; it was the first of the alkaloids to be synthesized.
Poison hemlock (Conium maculatum) contains not only highly toxic amounts of coniine, but also trace amounts of four other similarly poisonous alkaloids. Ingesting less than a tenth of a gram of coniine can be fatal for adult humans; this is approximately six to eight hemlock leaves. The seeds and roots are also toxic —more so than the leaves, in fact. While hemlock toxicity primarily results from consumption, poisoning can also result from inhalation, and from skin contact.
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