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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 non-competitive channel blocker for the GABA_A receptor chloride channels.^[3] It is therefore a channel blocker rather than a receptor antagonist.

On the other hand, evidence exists that picrotoxin acts as a competitive antagonist, and not as a channel blocker. For example, Newland and Cull-Candy (1992) found that when recording GABA-activated currents in neurons, picrotoxin "did not alter the amplitude of the main conductance state. However, picrotoxin did reduce the frequency of channel openings." They concluded, "Our data are consistent with a mechanism whereby picrotoxin binds preferentially to an agonist bound form of the receptor and stabilizes an agonist-bound shut state. This could, for example, mean that picrotoxin enhances the occurrence of a desensitized state or an allosterically blocked state." ^[4]

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.^[5]

Chemical structure

Picrotoxin is an equimolar mixture of two compounds, picrotoxinin (C₁₅H₁₆O₆; CAS# 17617-45-7) and picrotin (C₁₅H₁₈O₇; CAS# 21416-53-5).^[6]

Other uses

Picrotoxin is classified as an illegal performance-enhancing "Class 1 substance" by the American Quarter Horse Association.

References

^ Boullay, P. F. G. (1812). "Analyse chimique de la Coque du Levant, Menispermum cocculus". Bulletin de Pharmacie (in French) 4: 1–34. (Note: "Menispermum cocculus" has been renamed "Anamirta cocculus".)
^ Boullay, P. F. G. (1812). "Analyse chimique de la Coque du Levant, Menispermum cocculus". Bulletin de Pharmacie (in French) 4: 31. (Note: "Menispermum cocculus" has been renamed "Anamirta cocculus".)
^ Rho, J. M.; Donevan, S. D.; Rogawski, M. A. (1996). "Direct activation of GABA-A receptors by barbiturates in cultured rat hippocampal neurons". Journal of Physiology 497 (2): 509–522. doi:10.1113/jphysiol.1996.sp021784. PMC 1161000. PMID 8961191.
^ Newland, C. F.; Cull-Candy, S. G. (1992). "On the mechanism of action of picrotoxin on GABA receptor channels in dissociated sympathetic neurones of the rat". Journal of Physiology 447 (1): 191–213. doi:10.1113/jphysiol.1992.sp018998. PMC 1176032. PMID 1317428.
^ Nilsson, E.; Eyrich, B. (1950). "On Treatment of Barbiturate Poisoning". Acta Medica Scandinavica 137 (6): 381–389. doi:10.1111/j.0954-6820.1950.tb12129.x. PMID 15432128.
^ "Picrotoxin". Catalog. Sigma Aldrich.

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 Oto-Laryngologica 93 (3–4): 269–273. doi:10.3109/00016488209130882. PMID 7064710.
Dupont, L.; Dideberg, O.; Lamotte-Brasseur, J.; Angenot, L. (1976). "Structure cristalline et moléculaire de la picrotoxine, C₁₅H₁₆O₆·C₁₅H₁₈O₇". Acta Crystallographica B (in French) 32 (11): 2987–2993. doi:10.1107/S0567740876009424.
Olsen, R. W.; DeLorey, T. M. (1999). "GABA Receptor Physiology and Pharmacology". In Siegel G. J.; Agranoff, B. W.; Albers, R. W.; et al. Basic Neurochemistry: Molecular, Cellular and Medical Aspects (6th ed.). Philadelphia, PA, USA: Lippincott-Raven.

English Journal

Gating effects on picrotin block of glycine receptors.

Li P, Slaughter MM.SourceProgram in Neuroscience and Department of Physiology and Biophysical Sciences, University at Buffalo, Buffalo, New York 14214, USA.
Neuroreport.Neuroreport.2012 Dec 5;23(17):1017-20. doi: 10.1097/WNR.0b013e32835a8629.
Picrotoxin is a pore blocker that can differentiate ligand-gated inhibitory chloride channels. Even within one receptor type, such as the glycine receptor, picrotoxin block differs between subunits. The effect of subunit gating properties on block of the inhibitory glycine receptor (GlyR) was explor
PMID 23079787

Ginkgolide B and bilobalide block the pore of the 5-HT₃receptor at a location that overlaps the picrotoxin binding site.

Thompson AJ, Jarvis GE, Duke RK, Johnston GA, Lummis SC.SourceDepartment of Biochemistry, University of Cambridge, Tennis Court Road, Cambridge CB2 1QW, UK.
Neuropharmacology.Neuropharmacology.2011 Feb-Mar;60(2-3):488-95. doi: 10.1016/j.neuropharm.2010.11.003. Epub 2010 Nov 5.
Extracts from the Ginkgo biloba tree are widely used as herbal medicines, and include bilobalide (BB) and ginkgolides A and B (GA and GB). Here we examine their effects on human 5-HT(3)A and 5-HT(3)AB receptors, and compare these to the effects of the structurally related compounds picrotin (PTN) an
PMID 21059362

Stability of picrotoxin during yogurt manufacture and storage.

Jablonski JE, Jackson LS.SourceU.S. Food and Drug Administration (FDA), Natl. Center for Food Safety & Technology (NCFST), 6502 S. Archer Rd., Summit-Argo, IL 60501, USA. joseph.jablonski@fda.hhs.gov
Journal of food science.J Food Sci.2008 Oct;73(8):T121-8. doi: 10.1111/j.1750-3841.2008.00911.x.
Picrotoxin is a neurotoxin found in the berries of Anamirta cocculus, a plant native to Southeast Asia. Picrotoxin has potential for being used as a biological weapon since the toxin is relatively easy to isolate and purify. Limited information exists on the stability and detection of picrotoxin add
PMID 19019133

Japanese Journal

有機セレンをメディエー夕ーとするα,β-エポキシカルボニル化合物のβ-ヒドロキシカルボニル化合物(アルドール類)への官能基選択的還元と天然物合成への応用

有機合成化学協会誌 56(9), 736-744, 1998-09-01
NAID 10009343285

INDUCTION OF CYP2B SUBFAMILY P450 BY HIGHLY TOXIC INGREDIENTS IN PLANTS —ANIMAL-PLANT WARFARE AND THE EVOLUTION OF THE CYP2B P450—

薬物動態 9(supplement), 160-163, 1994
NAID 130003423671

有機セレン試薬の新展開とその天然物合成への応用

九州大学機能物質科学研究所報告 7(1), 47-52, 1993-09-30
NAID 110006177416

Related Pictures

Miscellaneous Bitter Principles Picrotoxin | Glycine antagonist | Abcam Buy tramadol from canada Picrotoxin- obtained as the bitter principle from the seed of Anamirta cocculus L cheapest price niaspan mesavineyard.com – Lovaza to buy Sensitive determination of picrotoxin by liquid chromatography-quadrupole time-of

★リンクテーブル★

リンク元

「ピクロトキシン」

Picrotoxin
	Picrotoxinin (left) and picrotin (right)
Identifiers
CAS Number	124-87-8
ATC code	None
PubChem	CID 5360688
IUPHAR/BPS	4051
DrugBank	DB00466
ChemSpider	16736444
UNII	ZLT174DL7U
KEGG	C09529
ChEMBL	CHEMBL506977
Chemical data
	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 ; Key:VJKUPQSHOVKBCO-AHMKVGDJSA-N ;
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英: picrotoxin
同: ピクロチン picrotin
関

概念

痙攣薬
ツヅラフジ科のAnamirta cocculusの種子の成分

作用機序

GABA_A受容体をブロック→Cl^-の透過性↓→ニューロンの興奮性↑

薬理作用

延髄および中脳に作用点をもち、中枢神経興奮させる　→　特異な間代性痙攣、大量で強直性痙攣

[1] Boullay, P. F. G. (1812). "Analyse chimique de la Coque du Levant, Menispermum cocculus". Bulletin de Pharmacie (in French) 4: 1–34. (Note: "Menispermum cocculus" has been renamed "Anamirta cocculus".)

[2] Boullay, P. F. G. (1812). "Analyse chimique de la Coque du Levant, Menispermum cocculus". Bulletin de Pharmacie (in French) 4: 31. (Note: "Menispermum cocculus" has been renamed "Anamirta cocculus".)

[3] Rho, J. M.; Donevan, S. D.; Rogawski, M. A. (1996). "Direct activation of GABA-A receptors by barbiturates in cultured rat hippocampal neurons". Journal of Physiology 497 (2): 509–522. doi:10.1113/jphysiol.1996.sp021784. PMC 1161000. PMID 8961191.

[4] Newland, C. F.; Cull-Candy, S. G. (1992). "On the mechanism of action of picrotoxin on GABA receptor channels in dissociated sympathetic neurones of the rat". Journal of Physiology 447 (1): 191–213. doi:10.1113/jphysiol.1992.sp018998. PMC 1176032. PMID 1317428.

[5] Nilsson, E.; Eyrich, B. (1950). "On Treatment of Barbiturate Poisoning". Acta Medica Scandinavica 137 (6): 381–389. doi:10.1111/j.0954-6820.1950.tb12129.x. PMID 15432128.

[6] "Picrotoxin". Catalog. Sigma Aldrich.

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picrotin