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Key Documents

P8390

Sigma-Aldrich

Picrotoxinin

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About This Item

Empirical Formula (Hill Notation):
C15H16O6
CAS Number:
Molecular Weight:
292.28
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.77

form

powder

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

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Jeffrey S Diamond
The Journal of neuroscience : the official journal of the Society for Neuroscience, 25(11), 2906-2916 (2005-03-18)
At many excitatory synapses, the neurotransmitter glutamate diffuses beyond the synaptic cleft to activate extrasynaptic targets. The extent and impact of such transmitter "spillover" on the processing capacity of neuronal networks are unclear, in part because it remains unknown how
N B Perry et al.
Phytochemical analysis : PCA, 12(1), 69-72 (2001-11-14)
Nuclear Overhauser effect spectroscopy (NOESY) gave full assignments of the 1H-NMR spectra of the picrotoxane neurotoxins tutin, hyenanchin, picrotoxinin and picrotin, as well as the solution conformations of these compounds, consistent with molecular modelling. Fully assigned 13C-NMR data are reported.
Jane E Carland et al.
European journal of pharmacology, 580(1-2), 27-35 (2007-11-23)
The relative impact on picrotoxinin activity of residues at the intracellular (2' and 6' residues) and extracellular (15' and 17' residues) ends of the second transmembrane (M2) domain of the human gamma-aminobutyric acid-C (GABA(C)) rho1 receptor was investigated. A series
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
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

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