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Sigma-Aldrich

Picrotoxinin

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About This Item

Empirische Formel (Hill-System):
C15H16O6
CAS-Nummer:
17617-45-7
Molekulargewicht:
292.28
MDL-Nummer:
MFCD00078765
UNSPSC-Code:
41116107
PubChem Substanz-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

InChIKey

PIMZUZSSNYHVCU-KBLUICEQSA-N

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Allgemeine Beschreibung

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

Anwendung

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. Wirkung

Picrotoxinin acts as a potent convulsant.
GABAA receptor antagonist; binds to the GABA receptor-linked Cl− channel.

Leistungsmerkmale und Vorteile

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.

Sonstige Hinweise

Active component of picrotoxin

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H300

Gefahreneinstufungen

Acute Tox. 2 Oral

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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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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