Cicutoxin (CTX)

Cicutoxin is a poisonous polyyne and alcohol found in various plants, such as the highly toxic water hemlock (Cicuta species). It is a natural product structurally related to the oenanthotoxin of hemlock water dropwort. The molecular formula for cicutoxin is C17H22O2. It is a aliphatic, highly unsaturated alcohol with two triple bonds, three double bonds and two hydroxyl groups. The natural form that occurs in plants is (R)-(-)-cicutoxin, but when cicutoxin is synthesized it is racemic mixture. There are also some closely related compounds that have almost the same structure cicutoxin such as Virol A and Virol C. When cicutoxin is isolated it is a yellowish oil. In the plant the compound is stable but when exposed to air, light or heat it becomes brown and cicutoxin is broken down. Because cicutoxin breaks down so rapidly, research on the compound isn’t easy.