Picrotoxin

Picrotoxin: Picrotoxin: picrotoxinin (left) and picrotin (right)

Picrotoxin

Clinical data

Pregnancy cat. ?

Legal status ?

Identifiers

CAS number 124-87-8^Y

ATC code None

PubChem CID 5360688

DrugBank APRD00269

ChemSpider 16736444^Y

UNII ZLT174DL7U^N

KEGG C09529^N

ChEMBL CHEMBL506977^N

Chemical data

Formula C₃₀H₃₄O₁₃

Mol. mass 602.583 g/mol

SMILES eMolecules & PubChem

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^Y
Key:VJKUPQSHOVKBCO-AHMKVGDJSA-N^Y

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Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound, first isolated by Pierre Boullay in 1812.^[1] The name "picrotoxin" is a combination of the Greek words "picros" (bitter) and "toxicon" (poison).^[2]

Found primarily in the fruit of the climbing plant Anamirta cocculus, it has a strong physiological action. It acts as a noncompetitive antagonist for the GABA_A receptor chloride channels. It is therefore a channel blocker rather than a receptor antagonist. As GABA itself is an inhibitory neurotransmitter, infusion of picrotoxin has stimulant and convulsant effects. As such, picrotoxin can be used to counter barbiturate poisoning, that can occur during general anesthesia or during a large intake outside of the hospital.^[3]

Contents

1 Chemical structure

2 Other uses

3 References

4 External links

Chemical structure

Picrotoxin (C₃₀H₃₄O₁₃) is an equimolar mixture of two compounds, picrotoxinin (C₁₅H₁₆O₆) and picrotin (C₁₅H₁₈O₇).^[4]

Other uses

Picrotoxin is classified as an illegal performance-enhancing "Class 1 substance" by the American Quarterhorse Association. The recommended penalty for a first offense is a one-year suspension and a $10,000 fine.

References

^ Pierre F. G. Boullay, "Analyse chimique de la Coque du Levant, Menispermum cocculus," Bulletin de Pharmacie, vol. 4, pages 1-34 (1812). (Note: "Menispermum cocculus" has been renamed "Anamirta cocculus".)

^ Pierre F. G. Boullay (1812) "Analyse chimique de la Coque du Levant, Menispermum cocculus," Bulletin de Pharmacie, vol. 4, page 31.

^ On Treatment of Barbiturate Poisoning, Nilson & Eyrich Acta Medica Scandinavica Volume 137 Issue 6, Pages 381-389.

^ Chemical structure of picrotoxin is available here: http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=P1675%7CSIGMA&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC.

External links

Ehrenberger K, Benkoe E, Felix D (1982). "Suppressive action of picrotoxin, a GABA antagonist, on labyrinthine spontaneous nystagmus and vertigo in man". Acta Otolaryngol. 93 (3–4): 269–73. doi:10.3109/00016488209130882. PMID 7064710.

L. Dupont, O. Dideberg, J. Lamotte-Brasseur et L. Angenot (1976). "Structure cristalline et moléculaire de la picrotoxine, C₁₅H₁₆O₆.C₁₅H₁₈O₇". Acta Cryst. B32: 2987–2993 (in French).

Basic Neurochemistry: GABA Receptor Physiology and Pharmacology.

v · d · eNeurotoxins

Animal Poisons & Venoms: Batrachotoxin • Bestoxin • Birtoxin • Bungarotoxin • Charybdotoxin • Conotoxin • Saxitoxin • Tetrodotoxin
Bacterial toxins: Botulinum toxin • Tetanospasmin
Fungal toxins: Bicuculline
Plant toxins: Penitrem A • Picrotoxin
Pesticides: Rotenone
Nerve agents: Cyclosarin EA-3148 • GV (nerve agent) • Novichok agent • Sarin • Soman • Tabun (nerve agent) • VE (nerve agent) • VG (nerve agent) • VM (nerve agent) • VR (nerve agent) • VX (nerve agent)
Neurotransmitters and precursors: Dopamine • Glutamate • L-Tyrosine • L-Phenylalanine • L-DOPA (Levodopa) • L-Glutamine
Neurotoxic drugs: Amphetamine • Lisdexamfetamine • Methamphetamine • αET • αMT • MBDB • MDA • MDEA • MDMA (Ecstasy) • PBA • PCA • PIA • 1,4-BD • GBL • GHB • Ibotenic Acid • Dizocilpine (MK-801) • Ketamine • Phencyclidine (PCP) • 5,7-DHT • 6-OHDA • MPTP/MPP+ • Norsalsolinol • Ethanol (Alcohol)

v · d · eGABAergics

Receptor
ligands

GABA_A

Agonists: Main site: Bamaluzole • Gaboxadol • Ibotenic acid • Isoguvacine • Isonipecotic acid • Muscimol (Amanita Muscaria) • Progabide • SL 75102 • Thiomuscimol • Tolgabide; Positive allosteric modulators: Barbiturates • Benzodiazepines • Carbamates • Chlormezanone • Clomethiazole • Ethanol (Alcohol) • Etomidate • Kavalactones (Kava) • Loreclezole • Metomidate • Neuroactive steroids • Nonbenzodiazepines (β-Carbolines, Cyclopyrrolones, Imidazopyridines, Pyrazolopyrimidines, etc.) • Phenols • Piperidinediones • Propanidid • Pyrazolopyridines • Quinazolinones • ROD-188 • Skullcap • Stiripentol • Valerenic acid (Valerian)
* See Template:GABAAergics for a full list of GABA_A positive allosteric modulators.
Antagonists: Main site: Bicuculline • Gabazine • Pitrazepin; Negative allosteric modulators: α5IA • Bilobalide • Cicutoxin • Cyclothiazide • DMCM • Flumazenil • Flurothyl • Furosemide • L-655,708 • Oenanthotoxin • Penicillin • Pentylenetetrazol • Picrotoxin • PWZ-029 • Ro15-4513 • Sarmazenil • Suritozole • Thujone (Absinthe) • Thiocolchicoside • ZK-93426

GABA_B

Agonists: Main site: 1,4-Butanediol • Baclofen • GBL • GHB • GHV • GVL • Lesogaberan • Phenibut • Progabide • SKF-97,541 • Tolgabide; Positive allosteric modulators: BHF-177 • BHFF • BSPP • CGP-7930 • GS-39783
Antagonists: Main site: CGP-35348 • Phaclofen • Saclofen • SCH-50911

GABA_C

Agonists: Main site: CACA • CAMP • GABOB • N(4)-chloroacetylcytosine arabinoside • Progabide • Tolgabide
Antagonists: Main site: Bilobalide • TPMPA

Reuptake
inhibitors

Plasmalemmal

GAT inhibitors

CI-966 • Deramciclane • EF-1502 • Gabaculine • Guvacine • Nipecotic acid • NNC 05-2090 • SKF-89976A • SNAP-5114 • Tiagabine

Enzyme
inhibitors

Anabolism

GAD inhibitors

Allylglycine

Catabolism

GABA-T inhibitors

3-Hydrazinopropionic acid • Aminooxyacetic acid • Gabaculine • Isoniazid • Phenelzine • Phenylethylidenehydrazine • Sodium valproate • Valnoctamide • Valproate pivoxil • Valproate semisodium (Divalproex sodium) • Valproic acid • Valpromide • Vigabatrin

Others

Precursors

Glutamate • Glutamine

Cofactors

Vitamin B6 (pyridoxine, pyridoxamine, pyridoxal phosphate)

Others

Gabapentin • L-Theanine • Picamilon • Pregabalin

v · d · eGlycinergics

Receptor
ligands

Agonists

Alanine • Cycloserine • Dimethylglycine • Glycine • Hypotaurine • Methylglycine (Sarcosine) • Milacemide • Serine • Taurine • Trimethylglycine (Betaine)

Antagonists

Bicuculline • Brucine • Caffeine • Picrotoxin • Pitrazepin • Strychnine • Thiocolchicoside • Tutin

Reuptake
inhibitors

Plasmalemmal

GlyT1 inhibitors

GlyT2 inhibitors

Vesicular

VIAAT Inhibitors

Enzyme
inhibitors

Anabolism/Catabolism

SHMT Inhibitors

GDC Inhibitors

DAAO Inhibitors

Others

Precursors

3-Phosphoglyceric acid • Serine

Cofactors

Vitamin B6 (Pyridoxine, pyridoxamine, pyridoxal → pyridoxal phosphate)

Categories:
GABA antagonists
Convulsants
Lactones

Picrotoxin


Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	124-87-8^Y
ATC code	None
PubChem	CID 5360688
DrugBank	APRD00269
ChemSpider	16736444^Y
UNII	ZLT174DL7U^N
KEGG	C09529^N
ChEMBL	CHEMBL506977^N
Chemical data
Formula	C₃₀H₃₄O₁₃
Mol. mass	602.583 g/mol
SMILES	eMolecules & PubChem
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^Y Key:VJKUPQSHOVKBCO-AHMKVGDJSA-N^Y
N(what is this?) (verify)

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Look at other dictionaries:

Picrotoxin — Pic ro*tox in, n. [Gr. ? bitter + toxic + in.] (Chem.) A bitter white crystalline substance found in the cocculus indicus. It is a peculiar poisonous neurotic and intoxicant, and consists of a mixture of several neutral substances. [1913 Webster] … The Collaborative International Dictionary of English
picrotoxin — [pik΄rō täk′sin] n. [ PICRO + TOXIN] a white, bitter, poisonous, crystalline compound, C30H34O13, resembling strychnine in its properties: used as a stimulant in cases of barbiturate poisoning … English World dictionary
Picrotoxin — Strukturformel Picrotin (oben), Picrotoxinin (unten) … Deutsch Wikipedia
picrotoxin — noun Etymology: International Scientific Vocabulary Date: 1815 a poisonous bitter crystalline stimulant and convulsive substance C30H34O13 obtained from the berry of a southeast Asian vine (Anamirta cocculus) and used intravenously as an antidote … New Collegiate Dictionary
picrotoxin — picrotoxic, adj. /pik reuh tok sin/, n. Pharm. a white, crystalline, bitter, poisonous, central nervous system stimulant, C30H34O13, obtained from the seeds of Anamirta cocculus: used chiefly in the treatment of barbiturate poisoning. [1865 70; … Universalium
picrotoxin — noun A poisonous material, extracted from the seeds of the Anamirta cocculus, used as a stimulant; it is a complex of two alkaloids picrotoxinin and picrotin Syn: cocculin … Wiktionary
picrotoxin — A very bitter neutral principle derived from the fruit of Anamirta cocculus (family Menispermaceae); a central nervous system stimulant, used as an antidote for poisoning by barbiturates and certain other CNS depressant drugs; a convulsant and… … Medical dictionary
picrotoxin — n. type of poison found in plant seeds … English contemporary dictionary
picrotoxin — pic·ro·tox·in … English syllables
picrotoxin — pic•ro•tox•in [[t]ˌpɪk rəˈtɒk sɪn[/t]] n. pha a poisonous stimulant, C30H34O13, obtained from the seeds of Anamirta cocculus, used to treat barbiturate poisoning • Etymology: 1865–70; < Gk pikr(ós) bitter + o +toxin … From formal English to slang

Academic Dictionaries and Encyclopedias

Picrotoxin

Contents

Chemical structure

Other uses

References

External links

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Academic Dictionaries and Encyclopedias

Wikipedia

Picrotoxin

Contents

Chemical structure

Other uses

References

External links

Look at other dictionaries:

Share the article and excerpts

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