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Merck

P1675

Picrotoxin

GABAA receptor antagonist, powder

Synonym(s):

Cocculin

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About This Item

Empirical Formula (Hill Notation):
C30H34O13
CAS Number:
124-87-8
Molecular Weight:
602.58
NACRES:
NA.77
PubChem Substance ID:
24278188
UNSPSC Code:
12352200
EC Number:
204-716-6
MDL number:
MFCD00074824
Beilstein/REAXYS Number:
3894406

Key Documents

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Product Name

Picrotoxin, powder

InChI key

VJKUPQSHOVKBCO-NGKRNLQBSA-N

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

SMILES string

[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

form

powder

color

white

mp

203 °C (lit.)

Quality Level

200

Gene Information

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

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Application

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

Biochem/physiol Actions

GABAA receptor antagonist; binds to the GABA receptor-linked Cl− channel.
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.

Features and Benefits

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.

General description

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.

Other Notes

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

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN8143
MKCN1128
MKCM0270
MKCL7566
MKCM6225

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Characterization of alpha 3 Glycine Receptors with Ginkgolide B and Picrotoxin
Chakrabarti S, et al.
bioRxiv, 454710-454710 (2018)
Picrotoxin-like channel blockers of GABAA receptors
Olsen RW
Proceedings of the National Academy of Sciences of the USA, 103(16), 6081-6082 (2006)
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
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)
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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