Cicutoxin

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Template:Chembox E number
Cicutoxin
Other names Cicutoxin
Identifiers
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Properties
C17H22O2
Molar mass 258.35 g/mol
Melting point
Boiling point
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Cicutoxin (chemical name: (8E,10E,12E,14R)-heptadeca-8,10,12-trien-4,6-diyne-1,14-diol; formula: C17H22O2) is a poisonous polyyne and alcohol found in various plants, most notably water hemlock. It is structural related to the oenanthotoxin of hemlock water dropwort.

It is a cholinergic poison, causing death by disruption of the central nervous system. It is a potent, noncompetitive gamma-aminobutyric acid (GABA) receptor antagonist. In humans, cicutoxin rapidly produces symptoms of nausea, emesis and abdominal pain, typically within 60 minutes of ingestion. This can lead to tremors and seizures.

References

  • Hazardous Substances Data Base
  • E. Anet, B. Lythgoe, M. H. Silk, S. Trippett (1953). "Oenanthotoxin and cicutoxin. Isolation and structures". J. Chem. Soc: 309–322. doi:10.1039/JR9530000309.
  • E. Anet, B. Lythgoe, M. H. Silk, S. Trippett (1952). "The Chemistry of Oenanthotoxin and Cicutoxin". Chemistry & Industry. 31: 757–758.
  • K. Uwai, K. Ohashi, Y. Takaya, T. Ohta, T. Tadano, K. Kisara, K. Shibusawa, R. Sakakibara, Y. Oshima (2000). "Exploring the Structural Basis of Neurotoxicity in C17-Polyacetylenes Isolated from Water Hemlock". Journal of Medical Chemistry. 43 (23): 4508–4515. doi:10.1021/jm000185k.
  • O. H. Knutsen, P. Paszkowski (1984). "New aspects in the treatment of water hemlock poisoning". In: Clin. Toxicol. 22: 157–166.

External links


de:Cicutoxin


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