Cicutoxin

Cicutoxin
IUPAC name (8E,10E,12E,14S)-heptadeca-8,10,12-triene-4,6-diyne-1,14-diol
Other names Cicutoxin
Identifiers
CAS number	505-75-9
ChemSpider	23215724
ChEMBL	CHEMBL140367
Jmol-3D images	Image 1
SMILES CCC[C@@H](O)\C=C\C=C\C=C\C#CC#CCCCO
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
Properties
Molecular formula	C17H22O2
Molar mass	258.35 g/mol
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, 100 kPa)
Infobox references

Cicutoxin is a poisonous polyyne and alcohol found in various plants, most notably water hemlock (Cicuta species). It is 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]

Footnotes

1. ^ Schep LJ, Slaughter RJ, Becket G, Beasley DM (April 2009). "Poisoning due to water hemlock". Clin Toxicol (Phila) 47 (4): 270–8. doi:10.1080/15563650902904332. PMID 19514873. 

References

• Hazardous Substances Data Base
• E. Anet, B. Lythgoe, M. H. Silk, S. Trippett (1953). "Oenanthotoxin and cicutoxin. Isolation and structures". J. Chem. Soc: 309–322. doi:10.1039/JR9530000309. 
• E. Anet, B. Lythgoe, M. H. Silk, S. Trippett (1952). "The Chemistry of Oenanthotoxin and Cicutoxin". Chemistry & Industry 31: 757–758. 
• K. Uwai, K. Ohashi, Y. Takaya, T. Ohta, T. Tadano, K. Kisara, K. Shibusawa, R. Sakakibara, Y. Oshima (2000). "Exploring the Structural Basis of Neurotoxicity in C17-Polyacetylenes Isolated from Water Hemlock". Journal of Medical Chemistry 43 (23): 4508–4515. doi:10.1021/jm000185k. PMID 11087575. 
• O. H. Knutsen, P. Paszkowski (1984). "New aspects in the treatment of water hemlock poisoning". In: Clin. Toxicol. 22 (2): 157–166. doi:10.3109/15563658408992551. PMID 6502788. 

This article about an alcohol is a stub. You can help Wikipedia by expanding it.v · Categories: Neurotoxins Plant toxins Alkynes Alkenes Alcohols GABA antagonists Convulsants Alcohol stubs Wikimedia Foundation. 2010. Игры ⚽ Нужна курсовая? Basketball at the 1976 Summer Olympics (team squads) Morinville, Alberta Look at other dictionaries: Cicutoxin — Cic u*tox in, n. (Chem.) The active principle of the water hemlock ({Cicuta}) extracted as a poisonous gummy substance. [1913 Webster] …   The Collaborative International Dictionary of English Cicutoxin — Strukturformel Allgemeines Name (8E,10E,12E,14R) Heptadeca 8,10,12 trien 4,6 diin 1,14 diol …   Deutsch Wikipedia cicutoxin — A toxic principle present in water hemlock, Cicuta virosa (family Umbelliferae); pharmacologic action is similar to that of picrotoxin. * * * cic·u·tox·in .sik yə täk sən, sik yə . n an amorphous poisonous principle C19H26O3 in water hemlock, s …   Medical dictionary cicutoxin — cic·u·toxin …   English syllables cicutoxin — |sikyə+ noun Etymology: International Scientific Vocabulary cicu (from New Latin Cicuta) + toxin : an amorphous poisonous principle C19H26O3 in plants of the genus Cicuta …   Useful english dictionary Cicuta — virosa Scientific classification Kingdom: Plantae …   Wikipedia Isocicutoxin — Strukturformel Allgemeines Name (8E,10E,12E,14R) Heptadeca 8,10,12 trien 4,6 diin 1,14 diol Andere Namen Cicutoxin …   Deutsch Wikipedia Oenanthotoxin — IUPAC name (2E,8E,10E,14R) heptadeca 2,8,10 triene 4,6 diyne 1,14 diol …   Wikipedia Cicuta virosa — Scientific classification Kingdom: Plantae (unranked): Angiosperm …   Wikipedia Cicuta douglasii — Scientific classification Kingdom: Plantae (unranked) …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”