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Merck
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安全信息

P1675

Sigma-Aldrich

Picrotoxin

powder

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别名:
Cocculin
经验公式（希尔记法）:
C30H34O13
CAS号:
124-87-8
分子量:
602.58
Beilstein:
3894406
EC 号:
204-716-6
MDL编号:
MFCD00074824
UNSPSC代码:
12352200
PubChem化学物质编号:
24278188
NACRES:
NA.77

形式

powder

质量水平

200

颜色

white

mp

203 °C (lit.)

SMILES字符串

[H][C@@]12C[C@@]3(O)[C@@]4([H])[C@H](C(C)=C)[C@]([H])(OC4=O)[C@@]5([H])OC(=O)[C@]1(O2)[C@@]35C.[H][C@@]67C[C@@]8(O)[C@@]9([H])[C@@H]([C@]([H])(OC9=O)[C@@]%10([H])OC(=O)[C@]6(O7)[C@@]8%10C)C(C)(C)O

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

InChI key

VJKUPQSHOVKBCO-NGKRNLQBSA-N

基因信息

human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562)

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一般描述

Picrotoxin is isolated from moonseed family, Menispermaceae. It is a stimulant and may cause convulsions. It is an allosteric modulator of γ-aminobutyric acid (GABAA) receptor.

应用

Picrotoxin has been used:
  • as non-competitive antagonist for the γ-aminobutyric acid (GABAA) for studying synchronized burst (SB) dynamics
  • as a component of extracellular saline for blocking glutamate and acetylcholine receptors in neurons
  • as a component of artificial cerebrospinal fluid (ACSF) for voltage-clamp recordings studies in dissociated cortical neurons

生化/生理作用

Picrotoxin is a competitive inhibitor of glycine receptors (GlyRs). It is a non-competitive antagonist, which binds to ligand bounded γ-aminobutyric acid (GABAA) receptor.
GABAA receptor antagonist; binds to the GABA receptor-linked Cl− channel.

特点和优势

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABAA Receptors and GABAC Receptors pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

其他说明

Molecular complex (1:1) of picrotin and picrotoxinin.
2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

象形图

Skull and crossbones
GHS06

警示用语：

Danger

危险声明

H300

危险分类

Acute Tox. 2 Oral

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

法规信息

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On the mechanism of action of picrotoxin on GABA receptor channels in dissociated sympathetic neurones of the rat
Newland CF and Cull-Candy SG
The Journal of Physiology, 447(1), 191-213 (1992)
Aric C Madayag et al.
Brain structure & function, 224(7), 2311-2324 (2019-06-16)
Despite evidence that morphine-related pathologies reflect adaptations in NAc glutamate signaling, substantial gaps in basic information remain. The current study examines the impact of non-contingent acute, repeated, and withdrawal-inducing morphine dosing regimens on glutamate transmission in D1- or D2-MSNs in
Picrotoxin-like channel blockers of GABAA receptors
Olsen RW
Proceedings of the National Academy of Sciences of the USA, 103(16), 6081-6082 (2006)
Characterization of alpha 3 Glycine Receptors with Ginkgolide B and Picrotoxin
Chakrabarti S, et al.
bioRxiv, 454710-454710 (2018)
Dynamic transitions among multiple oscillators of synchronized bursts in cultured neural networks
Kim JH, et al.
Journal of Statistical Mechanics: Theory and Experiment, 2014(4), P04019-P04019 (2014)
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