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oenanthotoxin

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Also known as enanthotoxin, (2E,8E,10E,14R)-2,8,10-heptadecatriene-4,6-diyne-1,14-diol, (+)-enanthotoxin, (+)-oenanthotoxin, (R)-enanthotoxin, (R)-oenanthotoxin

Oenanthotoxin is a toxin extracted from hemlock water-dropwort (Oenanthe crocata) and other plants of the genus Oenanthe. It is a central nervous system poison, and acts as a noncompetitive antagonist of the neurotransmitter gamma-aminobutyric acid. A case has been made for the presence of this toxin in local Oenanthe species playing a causative role in euthanasia in ancient Sardinia. It was crystallized in 1949 by Clarke and co-workers. It is structurally closely related to the toxins cicutoxin and carotatoxin. Oenanthotoxin is a C17 polyacetylene isomer of cicutoxin.

Wikidata facts

Mass
258.161979944
Show 4 more facts
chemical formula
C₁₇H₂₂O₂
isomeric SMILES
C(/C=C/C=C/C#CC#C/C=C/CO)C[C@@H](CCC)O
canonical SMILES
OCC=CC#CC#CC=CC=CCCC(O)CCC
Commons category
Oenanthotoxin
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5 sections
Contents
  • Occurrence
  • History and culture
  • Mechanism of action
  • Symptoms
  • References

Oenanthotoxin is a toxin extracted from hemlock water-dropwort (Oenanthe crocata) and other plants of the genus Oenanthe. It is a central nervous system poison, and acts as a noncompetitive antagonist of the neurotransmitter gamma-aminobutyric acid. A case has been made for the presence of this toxin in local Oenanthe species playing a causative role in euthanasia in ancient Sardinia. It was crystallized in 1949 by Clarke and co-workers. It is structurally closely related to the toxins cicutoxin and carotatoxin. Oenanthotoxin is a C17 polyacetylene isomer of cicutoxin.

==Occurrence== Oenanthotoxin concentration in plants is dependent on seasonal changes and geographical location, the most is present during late winter and early spring. Contrary to most poisonous plants that contain bitter tastes or burning sensations, the water dropwort has a rather sweet and pleasant taste and odor. Water dropwort is characterized by a yellow liquid that changes color due to air exposure. The roots are the most toxic part, although the entire plant contains poisonous properties.

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