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P8390

Sigma-Aldrich

Picrotoxinin

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About This Item

Empirical Formula (Hill Notation):
C15H16O6
CAS Number:
17617-45-7
Molecular Weight:
292.28
MDL number:
MFCD00078765
UNSPSC Code:
41116107
PubChem Substance ID:
24898746
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
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P301 + P310 + P330

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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Dian-Shi Wang et al.
The Journal of biological chemistry, 282(22), 16016-16035 (2007-04-05)
Contrary to its effect on the gamma-aminobutyric acid type A and C receptors, picrotoxin antagonism of the alpha1 homomeric glycine receptors (GlyRs) has been shown to be non-use-dependent and nonselective between the picrotoxin components picrotoxinin and picrotin. Picrotoxin antagonism of
Eyal Margalit et al.
Visual neuroscience, 28(2), 145-154 (2011-04-06)
Retinal prosthetic devices are being developed to bypass degenerated retinal photoreceptors by directly activating retinal neurons with electrical stimulation. However, the retinal circuitry that is activated by epiretinal stimulation is not well characterized. Whole-cell patch clamp recordings were obtained from
Xuebin Chen et al.
Neuropharmacology, 56(1), 318-327 (2008-07-29)
The dihydropyridines (DHPs), nifedipine and nicardipine, modulate native glycine receptors (GlyRs) at micromolar concentrations. Nicardipine has a biphasic potentiating and inhibitory effect, whereas nifedipine causes inhibition only. The present study sought to investigate (1) the molecular mechanism by which these
Zhe Yang et al.
Journal of neurochemistry, 103(2), 580-589 (2007-08-24)
Picrotoxin, an antagonist of structurally-rated GABA(A) receptors (GABA(A)Rs) and glycine receptors (GlyRs), is an equimolar mixture of picrotoxinin (PTXININ) and picrotin (PTN). These compounds share a common structure except that PTN contains a slightly larger dimethylmethanol in place of the
Ping Li et al.
Visual neuroscience, 24(4), 513-521 (2007-07-31)
GABA receptor antagonists produce an unexpectedly significant inhibition of native glycine receptors in retina and in alpha1 or alpha2 homomeric glycine receptors (GlyRs) expressed in HEK 293 cells. In this study we evaluate this phenomenon in heteromeric glycine receptors, formed
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