Cicutoxin

Cicutoxin
Names
	Preferred IUPAC name (8E,10E,12E,14R)-Heptadeca-8,10,12-triene-4,6-diyne-1,14-diol
	Other names Cicutoxin
Identifiers
CAS Number	505-75-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3695;
ChEMBL	ChEMBL140367;
ChemSpider	23215724;
KEGG	C08402;
PubChem CID	25265910;
UNII	6F9YP2TYQ0;
CompTox Dashboard (EPA)	DTXSID30896918 ;
	InChI 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;
	SMILES CCC[C@@H](O)\C=C\C=C\C=C\C#CC#CCCCO;
Properties
Chemical formula	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

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).^[1] 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.^[2]

It causes death by respiratory paralysis resulting from disruption of the central nervous system.^[2] 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.^[1] LD₅₀(mouse; i.p.) ~9 mg/kg^[3]

^ ^a ^b Cite error: The named reference Schep was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference Gung was invoked but never defined (see the help page).
^ Wink, Michael; Van Wyk, Ben-Erik (2008). Mind-Altering and Poisonous Plants of the World. Portland: Timber Press. p. 87. ISBN 9780881929522.