Picrotoxinin | CAS#17617-45-7 |

MedKoo Cat#: 592178 | Name: Picrotoxinin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Picrotoxinin negatively modulate the action of GABA on GABAA receptors.

Chemical Structure

Picrotoxinin

CAS#17617-45-7

Theoretical Analysis

MedKoo Cat#: 592178

Name: Picrotoxinin

CAS#: 17617-45-7

Chemical Formula: C15H16O6

Exact Mass: 292.0947

Molecular Weight: 292.29

Elemental Analysis: C, 61.64; H, 5.52; O, 32.84

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250mg	USD 480.00

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Synonym

Picrotoxinin; NSC 129537; NSC-129537; NSC129537

IUPAC/Chemical Name

(1aR-(1aalpha,2abeta,3beta,6beta,6abeta,8aS*,8bbeta,9R*))-Hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-3,6-methano-8H-1,5,7-trioxa cyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione

InChi Key

PIMZUZSSNYHVCU-YKWPQBAZSA-N

InChi Code

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

SMILES Code

O=C1[C@]([C@@H]2C(C)=C)([H])[C@]3(O)C[C@]4([H])[C@](O4)(C(O5)=O)[C@]3(C)[C@@]5([H])[C@]2([H])O1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Picrotoxinin, a potent convulsant, is a chloride channel blocker. Picrotoxinin is also a noncompetitive GABAA receptor antagonist.

In vitro activity:

Picrotoxinin is tenfold more potent for GABAA-ρ2 than for GABAA-ρ1 homomeric channels. This intra-subunit selectivity arises from the unconserved residues at the 2' sites, which are the essential molecular basis for both the binding and potency of picrotoxinin. The serine residues at the 2' positions of the ρ2 channel are predicted to form multiple hydrogen bonds and hydrophobic interactions with picrotoxinin, whereas the proline residues in the 2' positions of ρ1 channels are predicted to form only hydrophobic contacts with picrotoxinin. Reference: Comput Biol Chem. 2016 Oct;64:202-209. https://pubmed.ncbi.nlm.nih.gov/27423910/

In vivo activity:

Two strains of mice were shown to possess a differential sensitivity to picrotoxinin-induced convulsions; picrotoxinin elicited both tonic and clonic seizures at lower doses in the DBA/2J (DBA) strain compared to the BALB/c ByJ (BALB) strain. Biochemical studies revealed that picrotoxin inhibited 36Cl- efflux from forebrain synaptoneurosomes only in the DBA strain. In addition, picrotoxin inhibited pentobarbital-induced 36Cl- efflux to a greater extent in the DBA strain. Reference: Brain Res. 1989 Feb 27;481(1):169-74. https://pubmed.ncbi.nlm.nih.gov/2539878/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	100.0	342.13

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 292.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Naffaa MM, Samad A. The binding mode of picrotoxinin in GABAA-ρ receptors: Insight into the subunit's selectivity in the transmembrane domain. Comput Biol Chem. 2016 Oct;64:202-209. doi: 10.1016/j.compbiolchem.2016.07.003. Epub 2016 Jul 7. PMID: 27423910. 2. Yoon KW, Wotring VE, Fuse T. Multiple picrotoxinin effect on glycine channels in rat hippocampal neurons. Neuroscience. 1998 Dec;87(4):807-15. doi: 10.1016/s0306-4522(98)00158-4. PMID: 9759968. 3. Schwartz RD, Seale TW, Skolnick P, Paul SM. Differential seizure sensitivities to picrotoxinin in two inbred strains of mice (DBA/2J and BALB/c ByJ): parallel changes in GABA receptor-mediated chloride flux and receptor binding. Brain Res. 1989 Feb 27;481(1):169-74. doi: 10.1016/0006-8993(89)90499-x. PMID: 2539878.

In vitro protocol:

In vivo protocol:

1. Schwartz RD, Seale TW, Skolnick P, Paul SM. Differential seizure sensitivities to picrotoxinin in two inbred strains of mice (DBA/2J and BALB/c ByJ): parallel changes in GABA receptor-mediated chloride flux and receptor binding. Brain Res. 1989 Feb 27;481(1):169-74. doi: 10.1016/0006-8993(89)90499-x. PMID: 2539878.