ピクロトキシン
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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)
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Picrotoxin
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Picrotoxinin (left) and picrotin (right) |
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Clinical data |
Pregnancy cat. |
? |
Legal status |
? |
Identifiers |
CAS number |
124-87-8 Y |
ATC code |
None |
PubChem |
CID 5360688 |
IUPHAR ligand |
4051 |
DrugBank |
DB00466 |
ChemSpider |
16736444 Y |
UNII |
ZLT174DL7U Y |
KEGG |
C09529 N |
ChEMBL |
CHEMBL506977 Y |
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
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InChI
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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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N (what is this?) (verify)
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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 GABAA 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[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.
Neurotoxins
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Animal |
- Batrachotoxin
- Bestoxin
- Birtoxin
- Bungarotoxin
- Charybdotoxin
- Conotoxin
- Saxitoxin
- Tetrodotoxin
- Vanillotoxin
- Huwentoxin
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Bacterial |
- Botulinum toxin
- Tetanospasmin
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Plant |
- Penitrem A
- Picrotoxin
- Bicuculline
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Pesticides |
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Nerve agents |
- Cyclosarin
- EA-3148
- Novichok agent
- Sarin
- Soman
- Tabun
- VE
- VG
- VM
- VR
- VX
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Neurotoxic drugs |
- 1,4-BD
- 5,7-DHT
- 6-OHDA
- αET
- αMT
- Dizocilpine (MK-801)
- DSP-4
- Ethanol
- GBL
- GHB
- Ibotenic acid
- Ketamine
- Methamphetamine
- MBDB
- MDA
- MDEA
- MDMA (Ecstasy)
- MPP+
- MPTP
- Norsalsolinol
- PBA
- PCA
- PIA
- Phencyclidine (PCP)
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Denaturants |
Methanol
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GABAergics
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Receptor
ligands |
GABAA
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- Agonists: Main site: Bamaluzole
- Gaboxadol
- Ibotenic acid
- Isoguvacine
- Isonipecotic acid
- Muscimol (Amanita Muscaria)
- Progabide
- SL 75102
- Thiomuscimol
- Tolgabide; Positive allosteric modulators: Alcohols (2M2B, Ethanol, Ethchlorvynol, Methylpentynol)
- Barbiturates
- Benzodiazepines
- Carbamates
- Chlormezanone
- Clomethiazole
- 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)
Note: See the GABAA receptor PAMs navbox for a full list of GABAA positive allosteric modulators.
- Antagonists: Main site: Bicuculline
- Gabazine
- Pitrazepin
- Quisqualamine; Negative allosteric modulators: 17-Phenylandrostenol (17-PA)
- α5IA
- Bilobalide
- Cicutoxin
- Cyclothiazide
- DMCM
- Flumazenil
- Flurothyl
- Furosemide
- Iomazenil (123I)
- L-655,708
- Oenanthotoxin
- Penicillin
- Pentylenetetrazol
- Picrotoxin
- PWZ-029
- Radequinil
- Ro15-4513
- Sarmazenil
- Suritozole
- Terbequinil
- Thujone
- Thiocolchicoside
- ZK-93426
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GABAB
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- 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
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GABAC
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- Agonists: Main site: CACA
- CAMP
- GABOB
- N4-Chloroacetylcytosine arabinoside
- Progabide
- Tolgabide
Antagonists: Main site: Bilobalide
- TPMPA
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Reuptake
inhibitors |
Plasmalemmal
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GAT inhibitors
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- CI-966
- Deramciclane
- EF-1502
- Gabaculine
- Guvacine
- Nipecotic acid
- NNC 05-2090
- SKF-89976A
- SNAP-5114
- Tiagabine
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Enzyme
inhibitors |
Anabolism
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Catabolism
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GABA-T inhibitors
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- 3-Hydrazinopropionic acid
- Aminooxyacetic acid
- Gabaculine
- Isoniazid
- Phenelzine
- Phenylethylidenehydrazine
- Sodium valproate
- Valnoctamide
- Valproate pivoxil
- Valproate semisodium (Divalproex sodium)
- Valproic acid
- Valpromide
- Vigabatrin
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Others |
Precursors
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Cofactors
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- Vitamin B6 (pyridoxine
- pyridoxamine
- pyridoxal phosphate)
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Others
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- Gabapentin
- Hopantenic acid
- Picamilon
- Pregabalin
- L-Theanine
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Glycinergics
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Receptor
ligands |
Agonists
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- Alanine
- Cycloserine
- Dimethylglycine
- Glycine
- Hypotaurine
- Methylglycine (Sarcosine)
- Milacemide
- Quisqualamine
- Serine
- Taurine
- Trimethylglycine (Betaine)
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Antagonists
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- Bicuculline
- Brucine
- Caffeine
- Picrotoxin
- Pitrazepin
- Strychnine
- Thiocolchicoside
- Tutin
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Reuptake
inhibitors |
Plasmalemmal
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GlyT1 inhibitors
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Ethanol
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GlyT2 inhibitors
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Ethanol
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Vesicular
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Enzyme
inhibitors |
Anabolism/Catabolism
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SHMT Inhibitors
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GDC Inhibitors
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DAAO Inhibitors
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Others |
Precursors
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- 3-Phosphoglyceric acid
- Serine
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Cofactors
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- Vitamin B6 (Pyridoxine
- pyridoxamine
- pyridoxal → pyridoxal phosphate)
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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.
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 Links
- [Picrotoxin] [124-87-8] | 価格や在庫、物性値などの詳細情報ページです。 ... 絵表示 注意喚起語 危険 危険有害性情報 H300:飲み込むと生命に危険 注意書き P264:取扱い後はよく手を洗うこと。 P270
- Sigma-Aldrich offers Sigma-P1675, Picrotoxin for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Biochem/physiol Actions GABA A receptor antagonist; binds to the ...
Related Pictures
★リンクテーブル★
[★]
- 英
- respiratory stimulant, respiratory stimulants
- 関
- 延髄に直接作用して呼吸興奮と血圧上昇作用を示す。臨床応用は限られる (SPC.272)
- 過量:唾液分泌過多、悪心、嘔吐、不整脈、けいれん (SPC.272)
- 頚動脈体や大動脈体および延髄の化学受容器を刺激して呼吸興奮を起こす。即効性で持続時間は短い (SPC.272)
- 気道粘膜、食道および胃粘膜を刺激して反射的に呼吸興奮を起こす (SPC.272)
- 英
- respiratory stimulants
[★]
- 英
- GABAA receptor
- 関
- GABA受容体、GABA
- イオンチャネル型受容体
- α・β・γサブユニットからなり、αが1つ、βが2つ、γが2つからなる。
- アゴニストはGABAであり、βサブユニットへの結合に伴ってCl-チャネルが開口する
- 各種の薬物がサブユニットに結合し、アロステリック作用によりGABAの作用を増強する
- α:ベンゾジアゼピン
- β:バルビツール酸
- γ:エタノール
- β:picrotoxin cuculline
- GABAの作用を抑制する
[★]
- 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
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