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Picrotoxin information


Picrotoxin
Picrotoxinin (left) and picrotin (right)
Clinical data
ATC code
  • none
Identifiers
CAS Number
  • 124-87-8 checkY
PubChem CID
  • 5360688
IUPHAR/BPS
  • 4051
DrugBank
  • DB00466 checkY
ChemSpider
  • 16736444 checkY
UNII
  • ZLT174DL7U
KEGG
  • C09529 ☒N
ChEBI
  • CHEBI:134126 ☒N
ChEMBL
  • ChEMBL506977 checkY
CompTox Dashboard (EPA)
  • DTXSID7045605 Edit this at Wikidata
ECHA InfoCard100.004.288 Edit this at Wikidata
Chemical and physical data
3D model (JSmol)
  • Interactive image
SMILES
  • CC(=C)[C@H]1[C@@H]2C(=O)O[C@H]1[C@H]3OC(=O)[C@@]54O[C@@H]5C[C@]2(O)[C@@]34C.CC(C)(O)[C@H]5[C@@H]1C(=O)O[C@H]5[C@H]2OC(=O)[C@@]43O[C@@H]4C[C@]1(O)[C@@]23C
InChI
  • InChI=1S/C15H18O7.C15H16O6/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9;1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h5-9,18-19H,4H2,1-3H3;6-10,18H,1,4H2,2-3H3/t5-,6+,7-,8-,9-,13-,14-,15+;6-,7+,8-,9-,10-,13-,14-,15+/m11/s1 checkY
  • Key:VJKUPQSHOVKBCO-AHMKVGDJSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound. It was first isolated by the French pharmacist and chemist Pierre François Guillaume Boullay (1777–1869) in 1812.[1] The name "picrotoxin" is a combination of the Greek words "picros" (bitter) and "toxicon" (poison).[2] A mixture of two different compounds, picrotoxin occurs naturally in the fruit of the Anamirta cocculus plant, although it can also be synthesized chemically.

Due to its interactions with the inhibitory neurotransmitter GABA, picrotoxin acts as a stimulant and convulsant. It mainly impacts the central nervous system, causing seizures and respiratory paralysis in high enough doses.

  1. ^ Boullay PF (1812). "Analyse chimique de la Coque du Levant, Menispermum cocculus". Bulletin de Pharmacie (in French). 4: 5–34. Menispermum cocculus" has been renamed "Anamirta cocculus"
  2. ^ (Boullay, 1812), p. 31.

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Picrotoxin

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Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound. It was first isolated by the French pharmacist and chemist Pierre François...

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Pentylenetetrazol

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convulsant potency was strongly correlated to in vitro affinity to the picrotoxin binding site on the GABA-A receptor complex. Many GABA-A ligands, such...

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Anamirta cocculus

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Southeast Asian and Indian climbing plant. Its fruit is the source of picrotoxin, a poisonous compound with stimulant properties. The plant is large-stemmed...

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used in scientific research to study the GABA receptors. Picrotoxin Olsen, R. W (2006). "Picrotoxin-like channel blockers of GABAA receptors". Proceedings...

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Clomethiazole acts as a positive allosteric modulator at the barbiturate/picrotoxin site of the GABAA receptor. It works to enhance the action of the neurotransmitter...

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atropine to the patient. For animals, treatment consists of atropine, picrotoxin and activated charcoal. Scientists first attempted to determine the toxic...

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Methamphetamine

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MDMA

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GABA receptor

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been recognized that, for neurons that are stimulated by bicuculline and picrotoxin, the fast inhibitory response to GABA is due to direct activation of an...

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EPA list of extremely hazardous substances

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Phosphorus trichloride Physostigmine Physostigmine, salicylate (1:1) Picrotoxin Piperidine Pirimifos-ethyl Plutonium Polonium-210 Potassium arsenite Potassium...

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GABAA receptor negative allosteric modulator

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laudanosine, lindane, oenanthotoxin, pentylenetetrazol, phenylsilatrane, picrotoxin, radequinil, Ro15-4513, sarmazenil, suritozole, terbequinil,...

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Nitrous oxide

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levomethadone, levorphanol, morphine, oripavine, pethidine, thebaine) Picrotoxin (i.e., picrotin and picrotoxinin) PMBA Riluzole Tropeines (e.g., bemesetron...

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GABAA receptor

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

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Tetramethylenedisulfotetramine

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causing lethal convulsions. Its effect is similar to but stronger than picrotoxin, a GABA-A receptor antagonist widely used in research. As one of the most...

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Bicuculline

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by IUPHAR as a major criterion in the definition of GABAA receptors  Picrotoxin Hydrastine (very similar in structure) Johnston, Graham AR (2013). "Advantages...

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levomethadone, levorphanol, morphine, oripavine, pethidine, thebaine) Picrotoxin (i.e., picrotin and picrotoxinin) PMBA Riluzole Tropeines (e.g., bemesetron...

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Taurine

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