Cicutoxin

Title: Cicutoxin
CAS Registry Number: 505-75-9
CAS Name: (8E,10E,12E,14R)-8,10,12-Heptadecatriene-4,6-diyne-1,14-diol
Molecular Formula: C17H22O2
Molecular Weight: 258.36
Percent Composition: C 79.03%, H 8.58%, O 12.39%
Literature References: Poisonous principle of the water hemlock (Cicuta virosa L., Umbelliferae); naturally occurring as the (-)-form. Isoln: Jacobson, J. Am. Chem. Soc. 37, 916 (1915). Structure: Anet et al., J. Chem. Soc. 1953, 309. Synthesis of (±)-form: Hill et al., ibid. 1955, 1770. Antileukemic activity: T. Konoshima, K.-H. Lee, J. Nat. Prod. 49, 1117 (1986). Simple analytical method: R. A. Smith, D. Lewis, Vet. Hum. Toxicol. 29, 240 (1987).
Properties: Prisms from ether + petr ether, transformed in air and light to yellow oily resin. mp 54°. [a]D15 -14.5° (c = 1.7 in ethanol). Sol in alc, chloroform, ether, hot water, alkali hydroxides. Practically insol in petr ether. Very toxic.
Melting point: mp 54°
Optical Rotation: [a]D15 -14.5° (c = 1.7 in ethanol)
Derivative Type: (±)-Form
Properties: Crystals from ether + petr ether, mp 67°. uv max (alc): 242, 252, 318.5, 335.5 nm (e ´ 10-3 14.6, 21.6, 50.6, 60.3).
Melting point: mp 67°
Absorption maximum: uv max (alc): 242, 252, 318.5, 335.5 nm (e ´ 10-3 14.6, 21.6, 50.6, 60.3)
Cidofovir Cifenline Ciguatoxins Cilansetron Cilastatin

Cicutoxin
Cicutoxin.svg
Cicutoxin 3d structure.png
Identifiers
CAS number 505-75-9
ChemSpider 23215724
ChEMBL CHEMBL140367
Jmol-3D images Image 1
Properties
Molecular formula C17H22O2
Molar mass 258.36 g mol−1
Density 1.025 g/mL
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 (77 °F), 100 kPa)
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.[1] LD50(mouse; i.p.) ~9 mg/kg[2]