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P8390

Sigma-Aldrich

Picrotoxinin

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Empirical Formula (Hill Notation):
C15H16O6
CAS Number:
17617-45-7
Molecular Weight:
292.28
MDL number:
MFCD00078765
UNSPSC Code:
12352200
PubChem Substance ID:
24898746
NACRES:
NA.77

form

powder

Quality Level

200

SMILES string

[H][C@@]12OC(=O)[C@]([H])([C@@H]1C(C)=C)[C@]3(O)C[C@H]4O[C@]45C(=O)O[C@@]2([H])[C@]35C

InChI

1S/C15H16O6/c1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h6-10,18H,1,4H2,2-3H3/t6-,7+,8+,9-,10-,13-,14-,15+/m1/s1

InChI key

PIMZUZSSNYHVCU-KBLUICEQSA-N

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General description

Picrotoxinin is a component of picrotoxin and can be derived from plants. It is a non-nitrogenous compound.

Application

Picrotoxinin has been used as an agonist of taste 2 receptor member 14 (TAS2R14) to perform an array-based bitter receptor screening assay and to study the effect of calcium buffering and calcium sensor type on its sensitivity.

Biochem/physiol Actions

Picrotoxinin acts as a potent convulsant.
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 Glycine Receptor page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Active component of picrotoxin

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

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’.

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Xiu-Lian Ju et al.
Chemosphere, 69(6), 864-871 (2007-08-07)
A number of widely diverse compounds that show inhibitory activities at the picrotoxinin binding sites in housefly and rat GABA receptors were investigated by using the distance comparison technique (DISCOtech) and comparative molecular field analysis (CoMFA) methods to explore the
Allosteric ligands and their binding sites define $\gamma$-aminobutyric acid (GABA) type A receptor subtypes
Advances in Pharmacology, 73, 167-202 (2015)
Shelley H Huang et al.
European journal of pharmacology, 494(2-3), 131-138 (2004-06-24)
Ginkgolides A, B, and C are diterpene trilactones and active constituents of the 50:1 Ginkgo biloba leaf extract widely used in the symptomatic treatment of mild to moderate dementia. Using the two-electrode voltage clamp methodology, these ginkgolides were found to
J Baufreton et al.
Journal of neurophysiology, 86(1), 75-85 (2001-06-30)
The subthalamic nucleus (STN) influences the output of the basal ganglia, thereby interfering with motor behavior. The main inputs to the STN are GABAergic. We characterized the GABA(A) receptors expressed in the STN and investigated the response of subthalamic neurons
R Martín-Ruiz et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 21(24), 9856-9866 (2001-12-12)
We examined the in vivo effects of the hallucinogen 4-iodo-2,5-dimethoxyamphetamine (DOI). DOI suppressed the firing rate of 7 of 12 dorsal raphe (DR) serotonergic (5-HT) neurons and partially inhibited the rest (ED(50) = 20 microg/kg, i.v.), an effect reversed by
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