Cicutoxin

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Cicutoxin
IUPAC name	(8E,10E,12E,14S)-heptadeca-8,10,12-triene-4,6-diyne-1,14-diol
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 references

Cicutoxin is a poisonous polyyne and alcohol found in various plants, most notably water hemlock (Cicuta species). It is structurally 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, seizures, and death.

[edit] 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. 

[edit] External links

• Cicutoxin and other plant toxins

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