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Cicutoxin

Cicutoxin

Other names	Cicutoxin
Identifiers
CAS number	505-75-9
Properties
Molecular formula	C₁₇H₂₂O₂
Molar mass	258.35 g/mol
Melting point	54°C (prisms from ether & petroleum ether) 67°C (crystals from ether & petroleum ether)
Boiling point	Decomposes above 35°C
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.

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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

The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.

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.