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Other names Cicutoxin
CAS number 505-75-9
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.

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.


    • 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.
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cicutoxin". A list of authors is available in Wikipedia.
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