Cicutoxin

Cicutoxin is a naturally-occurring poisonous chemical compound produced by several plants from the family Apiaceae including water hemlock (Cicuta species) and water dropwort (Oenanthe crocata). The compound contains polyene, polyyne, and alcohol functional groups and is a structural isomer of oenanthotoxin, also found in water dropwort. Both of these belong to the C17-polyacetylenes chemical class.

Not to be confused with Ciguatoxin.
Cicutoxin
Names
Preferred IUPAC name
(8E,10E,12E,14R)-Heptadeca-8,10,12-triene-4,6-diyne-1,14-diol
Other names
Cicutoxin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10,12,15,17-19H,2,11,13-14,16H2,1H3/b6-4+,10-8+,15-12+/t17-/m1/s1
    Key: FQVNSJQTSOVRKZ-JNRDBWBESA-N
  • CCC[C@@H](O)\C=C\C=C\C=C\C#CC#CCCCO
Properties
C17H22O2
Molar mass 258.361 g·mol−1
Density 1.025 g/mL
Melting point 54 °C (129 °F; 327 K) (single enantiomer); 67 °C (racemic mixture)
Boiling point 467.2 °C (873.0 °F; 740.3 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It causes death by respiratory paralysis resulting from disruption of the central nervous system. It is a potent, noncompetitive antagonist of the gamma-aminobutyric acid (GABA) receptor. 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

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