17617-45-7

Usage

Biochem/physiol Actions

GABAA receptor antagonist; binds to the GABA receptor-linked Cl? channel.

Enzyme inhibitor

These neurotoxic GABAA receptor antagonists, consisting of a nearly 1:1 mixture of picrotoxinin, (FW = 292.29 g/mol; CAS 17617-45-7) and picrotin (FW = 310.30 g/mol; CAS 124-87-8), is a bitter-tasting (hence the Greek prefix picros) principle, also known as cocculin, from fishberry seeds (Anamirta cocculus) and the Philippine bayating (Tinomiscium philippinense). Picrotoxin binds to the chloride channel of the receptor without displacing g-aminobutyric acid. Picrotoxin is highly toxic, exerting both stimulant and convulsant effects, and care must be exercised when handling this agent.

InChI:InChI=1/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

Upstream product

• 124-87-8 (2aS)-2a,3c-epoxy-4a-hydroxy-9syn-(α-hydroxy-isopropyl)-8b-methyl-(2ar,4ac,8ac,8bc)-octahydro-1,7-dioxa-5c,8c-methano-cyclopent[cd]azulene-2,6-dione; compound with picrotoxinin 
• 242809-83-2 (S)-1-((1R,5R,7S,8R)-7-Bromomethyl-8-hydroxymethyl-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-yl)-but-3-yn-2-ol 
• 20744-71-2 β-Brom-picrotoxinin 
• 6485-40-1 (R)-Carvone 
• 242809-50-3 (1R,5S,8R,9S,11S)-9-Bromomethyl-5,9-dimethyl-10-oxa-tricyclo[6.2.1.0^1,5]undeca-3,6-diene-4,11-dicarboxylic acid 
• 242809-84-3 (1R,5S,8R,9S,11R)-9-(bromomethyl)-4-(acetoxymethyl)-5,9-dimethyl-11-(hydroxymethyl)-10-oxotricyclo<6.2.1.0^1.5>undec-3,6-diene 
• 172172-82-6 C₂₁H₂₈O₉ 
• 172172-83-7 (2aS,3R,4aR,5S,6R,7R,7aS,7bR)-7-Acetoxy-2a,3,4a-trihydroxy-6-isopropenyl-7b-methyl-2-oxo-decahydro-indeno[7,1-bc]furan-5-carboxylic acid methyl ester 
• 172172-81-5 C₁₉H₂₆O₈ 
• 172172-71-3 (1R,5R,7S,8R)-7-Bromomethyl-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-8-(tert-butyl-dimethyl-silanyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-ene 
• 172172-80-4 C₁₉H₂₆O₈ 
• 172172-70-2 (1R,3R,5S,8R,9S,11R)-9-(bromomethyl)-3-<(tert-butyldimethylsilyl)oxy>-11-<<(tert-butyldimethylsilyl)oxy>methyl>-5,9-dimethyl-4-methylidine-10-oxotricyclo<6.2.1.0^1.5>undec-6-ene 
• 172172-79-1 8,9-dihydroxy-β-bromopicrotoxinic acid methyl ester 
• 172172-96-2 (1R,2R,4R,5S,6R,7R,10S,11R)-2,4,5,11-tetrahydroxy-10-isopropenyl-6-methyl-9-oxo-8-oxatricyclo<5.2.2.0^2,6>undecane-5-carboxylic acid methyl ester 

Downstream Products

• 119619-32-8 13-(Phenylseleno)picrotin 
• 21416-53-5 picrotin 
• 17617-46-8 α-dihydropicrotoxinin 
• 5947-63-7 (2aS)-9syn-acetyl-2a,3c-epoxy-4a-hydroxy-8b-methyl-(2ar,4ac,8ac,8bc)-octahydro-1,7-dioxa-5c,8c-methano-cyclopent[cd]azulene-2,6-dione 
• 1909-79-1 2-methyl-2-cyclopenten-1-one-3-carboxylic acid 

Relevant academic research and scientific papers

Stereocontrolled Total Synthesis of (-)-Picrotoxinin and (+)-Coriamyrtin via a Common Isotwistane Intermediate

Stereocontrolled total synthesis of (-)-picrotoxinin (1) and (+)-coriamyrtin (2), toxic sesquiterpenoids of plant origin, is described, utilizing isotwistane compounds as common and key intermediates.

Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation

We report a concise, stereocontrolled synthesis of the neurotoxic sesquiterpenoid (-)-picrotoxinin (1, PXN). The brevity of the route is due to regio-and stereoselective formation of the [4.3.0] bicyclic core by incorporation of a symmetrizing geminal dim

SHORT SYNTHESES OF (-)-PICROTOXININ AND RELATED COMPOUNDS

The present disclosure relates to concise processes for making (?)-picrotoxinin (1, PXN) and 5-methyl-picrotoxinin (20, 5MePXN), and to 5MePXN, its pharmaceutical compositions, and its method of use for inhibiting GABAA receptor.

Palladium-catalyzed enyne cycloisomerization reaction in an asymmetric approach to the picrotoxane sesquiterpenes. 2. Second-generation total syntheses of corianin, picrotoxinin, picrotin, and methyl picrotoxate

An alternative, more efficient synthesis of the picrotoxane core by palladium-catalyzed cycloisomerization of an enyne requires the design of a new catalyst system based upon 1,3-bis(dibenzophospholyl)propane and 2- (diphenylphosphino)benzoic acid as liga

Stereoselective Total Synthesis of (-)-Picrotoxnin and (-)-Picrotin

The stereoselective total synthesis of (-)-picritoxnin (1) and (-)-picrotin (2), starting from (+)-5β-hydroxycarvone (3), is described.Eight contiguous asymmetric centers on a cis-fused hydrindane ring system were stereoselectively prepared via three key