Skip to Content
MilliporeSigma
All Photos(3)

Documents

P1675

Sigma-Aldrich

Picrotoxin

powder

Synonym(s):

Cocculin

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

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

form

powder

Quality Level

200

color

white

mp

203 °C (lit.)

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

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

Gene Information

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

Looking for similar products? Visit Product Comparison Guide

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.

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

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.

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.

Other Notes

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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 6

1 of 6

4-Aminopyridine ≥99%

Sigma-Aldrich

275875

4-Aminopyridine

Muscimol powder

Sigma-Aldrich

M1523

Muscimol

1(S),9(R)-(−)-Bicuculline methbromide ≥98% (HPLC), solid

Sigma-Aldrich

B7561

1(S),9(R)-(−)-Bicuculline methbromide

DL-2-Amino-5-phosphonopentanoic acid solid

Sigma-Aldrich

A5282

DL-2-Amino-5-phosphonopentanoic acid

SR95531 (Gabazine)

Sigma-Aldrich

5.05986

SR95531 (Gabazine)

Kynurenic acid ≥98%

Sigma-Aldrich

K3375

Kynurenic acid

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)
View All Related Papers

Related Content

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service