cicutoxin

Also known as R-(-)-cicutoxin, (8E,10E,12E,14R)-heptadeca-8,10,12-trien-4,6-diyne-1,14-diol, cicutotoxin

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) and bupleurotoxin (found in Bupleurum longiradiatum). All of these belong to the C17-polyacetylenes chemical class.

Chemical data

Formula: C17H22O2
Molecular weight: 258.35 g/mol
IUPAC name: (8E,10E,12E,14R)-heptadeca-8,10,12-trien-4,6-diyne-1,14-diol
SMILES: CCC[C@H](/C=C/C=C/C=C/C#CC#CCCCO)O
InChIKey: FQVNSJQTSOVRKZ-JNRDBWBESA-N
XLogP: 3.3
Polar surface area: 40.5 Å²
H-bond donors: 2
H-bond acceptors: 2
Formal charge: 0

via PubChem

Wikidata facts

Mass: 258.161979944

Show 4 more facts

isomeric SMILES: CCC[C@H](/C=C/C=C/C=C/C#CC#CCCCO)O
chemical formula: C₁₇H₂₂O₂
canonical SMILES: OCCCC#CC#CC=CC=CC=CC(O)CCC
Commons category: Cicutoxin

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Article

14 sections

Contents

History
Plants containing cicutoxin
Chemistry
Laboratory synthesis
Biochemistry
Mechanism of action
Metabolism
Poisoning
Symptoms
Treatment
Effects on animals
Medical use
References
Additional 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