Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/11/26 19:29:56」(JST)

wiki en

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]

Chemical structure[edit]

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

Other uses[edit]

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[edit]

^ 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".)
^ 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. edit
^ "Picrotoxin". Catalog. Sigma Aldrich.

External links[edit]

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.
Siegel G. J.; Agranoff, B. W.; Albers, R. W. et al., ed. (1999). "GABA Receptor Physiology and Pharmacology". Basic Neurochemistry: Molecular, Cellular and Medical Aspects (6th ed.). Philadelphia, PA, USA: Lippincott-Raven.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. ストリキニーネ中毒 strychnine poisoning
2. 痙攣発作およびてんかんの病態生理 pathophysiology of seizures and epilepsy
3. 殺鼠剤中毒の概要 overview of rodenticide poisoning
4. 抗てんかん剤：作用機序、薬理学、および有害事象 antiepileptic drugs mechanism of action pharmacology and adverse effects

English Journal

Glyoxalase 1 and its substrate methylglyoxal are novel regulators of seizure susceptibility.

Distler MG, Gorfinkle N, Papale LA, Wuenschell GE, Termini J, Escayg A, Winawer MR, Palmer AA.SourceDepartment of Pathology, University of Chicago, Chicago, Illinois, U.S.A.
Epilepsia.Epilepsia.2013 Apr;54(4):649-57. doi: 10.1111/epi.12121. Epub 2013 Feb 14.
PURPOSE: Epilepsy is a complex disease characterized by a predisposition toward seizures. There are numerous barriers to the successful treatment of epilepsy. For instance, current antiepileptic drugs have adverse side effects and variable efficacies. Furthermore, the pathophysiologic basis of epile
PMID 23409935

Meta-diamide insecticides acting on distinct sites of RDL GABA receptor from those for conventional noncompetitive antagonists.

Nakao T, Banba S, Nomura M, Hirase K.SourceAgrochemicals Research Center, Mitsui Chemicals Agro, Inc., Mobara, Chiba 297-0017, Japan. Electronic address: Toshifumi.Nakao@mitsui-chem.co.jp.
Insect biochemistry and molecular biology.Insect Biochem Mol Biol.2013 Apr;43(4):366-75. doi: 10.1016/j.ibmb.2013.02.002. Epub 2013 Feb 14.
The RDL GABA receptor is an attractive target of insecticides. Here we demonstrate that meta-diamides [3-benzamido-N-(4-(perfluoropropan-2-yl)phenyl)benzamides] are a distinct class of RDL GABA receptor antagonists showing high insecticidal activity against Spodoptera litura. We also suggest that th
PMID 23416568

Japanese Journal

Inhibitory Activities on Mammalian Central Nervous System Receptors and Computational Studies of Three Sesquiterpene Lactones from Coriaria ruscifolia subsp. ruscifolia

Perez Claudia,Becerra Jose,Manriquez-Navarro Paula [他],Aguayo Luis Gerardo,Fuentealba Jorge,Guzmán José Leonardo,Joseph-Nathan Pedro,Jiménez Verónica,Muñoz Marcelo Andrés,Silva Mario
CHEMICAL & PHARMACEUTICAL BULLETIN 59(2), 161-165, 2011
The electrophysiological characterization of sesquiterpene lactones from Coriaria ruscifolia subsp. ruscifolia has been tested on hippocampal neurons. The results for glycinergic rat hippocampal trans …
NAID 130000405509

Activation of Bombesin receptor subtype-3 influences activity of orexin neurons by both direct and indirect pathways

Furutani Naoki 　,Hondo Mari 　,Tsujino Natsuko,Sakurai Takeshi　,辻野なつ子,櫻井武
Journal of Molecular Neuroscience 42(1), 106-111, 2010-09
… Moreover, in the presence of GABA receptor blockers, picrotoxin and CGP55845, the BRS3 agonist induced depolarization and increased firing frequency. …
NAID 120002384286

Related Pictures

★リンクテーブル★

リンク元	「呼吸興奮薬」「GABAA受容体」「ピクロトキシン」

「呼吸興奮薬」

Picrotoxin
	Picrotoxinin (left) and picrotin (right)
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	124-87-8
ATC code	None
PubChem	CID 5360688
IUPHAR ligand	4051
DrugBank	DB00466
ChemSpider	16736444
UNII	ZLT174DL7U
KEGG	C09529
ChEMBL	CHEMBL506977
Chemical data
Formula	?
	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 ;
(what is this?) (verify);