Cicutoxin
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| Names | |
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IUPAC name
(8E,10E,12E,14R)-heptadeca-8,10,12-triene-4,6-diyne-1,14-diol
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| Other names
Cicutoxin
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| Identifiers | |
| 505-75-9 | |
| 3D model (Jmol) | Interactive image |
| ChEMBL | ChEMBL140367 |
| ChemSpider | 23215724 |
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| Properties | |
| C17H22O2 | |
| Molar mass | 258.36 g·mol−1 |
| Density | 1.025 g/mL |
| Melting point | 54 °C (129 °F; 327 K) (prisms from ether & petroleum ether); 67 °C (crystals from ether & petroleum ether) |
| Boiling point | Decomposes above 35 °C (95 °F; 308 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Cicutoxin is a poisonous polyyne and alcohol found in various plants, such as the highly toxic water hemlock (Cicuta species). It is a natural product structurally related to the oenanthotoxin of hemlock water dropwort.
It causes 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. LD50(mouse; i.p.) ~9 mg/kg
The toxic effect of the plants that contains cicutoxin have been known for centuries. As early as 1911, 27 cases of cicutoxin poisoning were known, 21 of the cases resulted in death. In some of these cases the plant was used for murder or execution. 78 cases were reported in 1962, 33 of them resulted in death. These days there are still cases of cicutoxin poisoning:
-A child used the stem of a plant as a toy whistle and died of cicutoxin poisoning
-A 14-year-old boy died 20 hours after consuming a ‘wild carrot’
-In 1992, two brothers were foraging for wild ginseng, one of them ate three bites of a ‘ginseng’-root and the other one ingested one bite. The first brother died three hours after ingesting the root. His brother only suffered seizures and delirium, but had full recovery
-A family of five used a cicuta plant to relieve themselves of pruritus. The cicutoxin caused toxic symptoms and two of the children died.
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Wikipedia