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Cicutoxin information


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 Edit this at Wikidata
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]

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

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Cicutoxin

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Cicutoxin is a naturally-occurring poisonous chemical compound produced by several plants from the family Apiaceae including water hemlock (Cicuta species)...

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Cicuta

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poisonous to humans. Three members of the genus contain a toxin named cicutoxin which causes central nervous system stimulatory effects including seizures...

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Cicuta virosa

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Musquash-poison. The plant contains cicutoxin, which disrupts the workings of the central nervous system. In humans, cicutoxin rapidly produces symptoms of nausea...

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Oenanthotoxin

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structurally closely related to the toxins cicutoxin and carotatoxin. Oenanthotoxin is a C17 polyacetylene isomer of cicutoxin. Oenanthotoxin concentration in plants...

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Cicuta douglasii

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is its toxicity. Cicutoxin is the toxin that is produced, making water hemlock the most poisonous plant in North America. Cicutoxin is a yellowish liquid...

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Cicuta maculata

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the plant causing death in as little as 15 minutes. The chief poison is cicutoxin, an unsaturated aliphatic alcohol that is most concentrated in the roots...

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GABAA receptor

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barbiturates, alcohol (ethanol), inhaled anaesthetics, kavalactones, cicutoxin, and picrotoxin, among others. Much like the GABAA receptor, the GABAB...

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Fish

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Phenibut

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GABAA receptor negative allosteric modulator

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mostly non-selective, include amentoflavone, bemegride, bilobalide, cicutoxin, dieldrin, FG-7142, fipronil, flurothyl, iomazenil, laudanosine, lindane...

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Alkyne

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other members of the Asteraceae and Apiaceae families). Some examples are cicutoxin, oenanthotoxin, and falcarinol. These compounds are highly bioactive,...

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Lemon balm

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(TBPS, TBPO, IPTBO) BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB...

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Baclofen

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Substances poisonous to dogs

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are cows or other grazing animals. If a dog does ingest hemlock, the cicutoxin in the plant can be fatal very quickly as it causes the heart and nervous...

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Furosemide

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Falcarinol

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bend in the molecule. It is structurally related to oenanthotoxin and cicutoxin. Falcarinol is an intense irritant that can cause allergic reactions and...

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Ricin

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Toxin

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Glossary of chemical formulae

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C17H19N3O3S omeprazole 73590-58-6 C17H21NO4 cocaine 50-36-2 53-21-4 C17H22O2 cicutoxin C17H22O2 oenanthotoxin C17H24O falcarinol C17H24O9 Eleutheroside B Syringin...

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RDX

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Botulinum toxin

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Penicillin

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GABA

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thujone, flumazenil Uncompetitive antagonist (e.g., channel blocker) cicutoxin Negative allosteric modulators furosemide, oenanthotoxin, amentoflavone...

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Resiniferatoxin

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Levofloxacin

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List of poisonous plants

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freshly pulled out of the ground, is extremely poisonous and contains cicutoxin, a central nervous system stimulant that induces seizures.[citation needed]...

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Glutamine

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Aflatoxin B1

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