Picrotoxin | CAS#124-87-8 | stimulant

MedKoo Cat#: 592104 | Name: Picrotoxin

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Description:

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

Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound. Due to its interactions with the inhibitory neurotransmitter GABA, picrotoxin acts as a stimulant and convulsant.

Chemical Structure

Picrotoxin

CAS#124-87-8

Theoretical Analysis

MedKoo Cat#: 592104

Name: Picrotoxin

CAS#: 124-87-8

Chemical Formula: C30H34O13

Exact Mass: 602.1999

Molecular Weight: 602.59

Elemental Analysis: C, 59.80; H, 5.69; O, 34.52

Price and Availability

Size	Price	Availability	Quantity
1g	USD 240.00
5g	USD 470.00

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Synonym

Picrotoxin; NSC 403139; NSC-403139; NSC403139

IUPAC/Chemical Name

3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1aR,2aR,3S,6R,6aS,8aS,8bR,9S)-, compd. with (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-3,6-methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione (1:1)

InChi Key

VJKUPQSHOVKBCO-ZZJBNGRXSA-N

InChi Code

InChI=1S/C15H18O7.C15H16O6/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9;1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h5-9,18-19H,4H2,1-3H3;6-10,18H,1,4H2,2-3H3/t5-,6-,7-,8-,9-,13-,14-,15+;/m1./s1

SMILES Code

O=C1[C@]([C@H]2C(C)(O)C)([H])[C@]3(O)C[C@]4([H])[C@](O4)(C(O5)=O)[C@]3(C)[C@@]5([H])[C@]2([H])O1.O=C6C(C7C(C)=C)C8(O)CC9C(O9)(C(O%10)=O)C8(C)C%10C7O6

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:

Picrotoxin (Picrotin, Cocculin, Cocculus, NSC 403139), a plant alkaloid, is a non-competitive antagonist of neuronal GABA and glycine receptors.

In vitro activity:

The first two subunits of the glutamate-gated chloride channel family, GluClalpha and GluClbeta, were cloned from the free living nematode Caenorhabditis elegans. This study analyzed the blockade of these novel channels by picrotoxin. In vitro synthesized GluClalpha and GluClbeta RNAs were injected individually or coinjected into Xenopus oocytes. The EC50 values for picrotoxin block of homomeric GluClalpha and GluClbeta were 59 microM and 77 nM, respectively. Picrotoxin block of homomeric GluClbeta channels was promoted during activation of membrane current with glutamate. In addition, recovery from picrotoxin block was faster during current activation by glutamate. Reference: J Neurochem. 1999 Jan;72(1):318-26. https://pubmed.ncbi.nlm.nih.gov/9886084/

In vivo activity:

The present study examined whether exposure to the GABAA receptor antagonist picrotoxin causes ASD-like pathophysiology in offspring by conducting behavioral tests from the juvenile period to adulthood and performing gene expression analyses in mature mouse brains. Here, we found that male mice that were prenatally exposed to picrotoxin exhibited a reduction of active interaction time in the social interaction test in both adolescence and adulthood. The gene expression analyses showed that picrotoxin-exposed male mice exhibited a significant increase in the gene expression of odorant receptors. Reference: Front Psychiatry. 2022 Feb 3;13:821354. https://pubmed.ncbi.nlm.nih.gov/35185658/

	Solvent	mg/mL	mM
Solubility
	Ethanol	57.5	95.42
	DMSO	47.4	78.58
	DMSO:PBS (pH 7.2) (1:3)	0.3	0.41

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 602.59 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. Etter A, Cully DF, Liu KK, Reiss B, Vassilatis DK, Schaeffer JM, Arena JP. Picrotoxin blockade of invertebrate glutamate-gated chloride channels: subunit dependence and evidence for binding within the pore. J Neurochem. 1999 Jan;72(1):318-26. PMID: 9886084. 2. Newland CF, Cull-Candy SG. On the mechanism of action of picrotoxin on GABA receptor channels in dissociated sympathetic neurones of the rat. J Physiol. 1992 Feb;447:191-213. doi: 10.1113/jphysiol.1992.sp018998. PMID: 1317428; PMCID: PMC1176032. 3. Kotajima-Murakami H, Hagihara H, Sato A, Hagino Y, Tanaka M, Katoh Y, Nishito Y, Takamatsu Y, Uchino S, Miyakawa T, Ikeda K. Exposure to GABAA Receptor Antagonist Picrotoxin in Pregnant Mice Causes Autism-Like Behaviors and Aberrant Gene Expression in Offspring. Front Psychiatry. 2022 Feb 3;13:821354. doi: 10.3389/fpsyt.2022.821354. PMID: 35185658; PMCID: PMC8850354. 4. Dombrowski PA, Fernandes LH, Andreatini R. Picrotoxin blocks the anxiolytic- and panicolytic-like effects of sodium valproate in the rat elevated T-maze. Eur J Pharmacol. 2006 May 10;537(1-3):72-6. doi: 10.1016/j.ejphar.2006.03.037. Epub 2006 Mar 24. PMID: 16626689.

In vitro protocol:

In vivo protocol:

1. Kotajima-Murakami H, Hagihara H, Sato A, Hagino Y, Tanaka M, Katoh Y, Nishito Y, Takamatsu Y, Uchino S, Miyakawa T, Ikeda K. Exposure to GABAA Receptor Antagonist Picrotoxin in Pregnant Mice Causes Autism-Like Behaviors and Aberrant Gene Expression in Offspring. Front Psychiatry. 2022 Feb 3;13:821354. doi: 10.3389/fpsyt.2022.821354. PMID: 35185658; PMCID: PMC8850354. 2. Dombrowski PA, Fernandes LH, Andreatini R. Picrotoxin blocks the anxiolytic- and panicolytic-like effects of sodium valproate in the rat elevated T-maze. Eur J Pharmacol. 2006 May 10;537(1-3):72-6. doi: 10.1016/j.ejphar.2006.03.037. Epub 2006 Mar 24. PMID: 16626689.

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