CAS 17617-45-7: (-)-Picrotoxinin

Description: (-)-Picrotoxinin is a naturally occurring organic compound classified as a bicyclic sesquiterpene. It is primarily derived from the seeds of the plant Anamirta cocculus, commonly known as the fish berry or cocculus indicus. This compound is known for its neurotoxic properties, acting as a potent antagonist of the GABA_A receptor, which plays a crucial role in inhibitory neurotransmission in the central nervous system. As a result, (-)-Picrotoxinin can induce convulsions and has been studied for its effects on neuronal excitability. The substance is typically encountered as a white crystalline solid and is soluble in organic solvents but has limited solubility in water. Due to its toxic nature, it is important to handle (-)-Picrotoxinin with caution in laboratory settings. Its applications extend to research in neuropharmacology and toxicology, where it serves as a valuable tool for studying GABAergic signaling pathways. However, due to its toxicity, it is not used therapeutically in humans.

Formula: C₁₅H₁₆O₆

InChI: 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: InChIKey=PIMZUZSSNYHVCU-YKWPQBAZSA-N

SMILES: O=C1OC2C3OC(=O)C45OC5CC(O)(C1C2C(=C)C)C34C

Synonyms:

• (1aR,2aR,3R,6S,6aS,8aS,8bR,9R)-2a-hydroxy-8b-methyl-9-(prop-1-en-2-yl)hexahydro-3,6-methano-1,5,7-trioxacyclopenta[ij]cyclopropa[a]azulene-4,8(3H)-dione
• (1aR,2aR,3R,6S,8aS,8bR,9R)-2a-hydroxy-8b-methyl-9-(1-methylethenyl)hexahydro-3,6-methano-1,5,7-trioxacyclopenta[ij]cyclopropa[a]azulene-4,8(3H)-dione
• (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
• (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
• 2a-hydroxy-8b-methyl-9-(prop-1-en-2-yl)hexahydro-3,6-methano-1,5,7-trioxacyclopenta[ij]cyclopropa[a]azulene-4,8(3H)-dione
• 3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-, (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-
• 3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-, (1aR-(1a-alpha,2a-beta,3-beta,6-beta,6a-beta,8as*,8b-beta,9R*))-
• 3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-, [1aR-(1aα,2aβ,3β,6β,6aβ,8aS*,8bβ,9R*)]-
• Ai3-41571
• Nsc 129537
• Picrotoxinin (from Anamirta cocculus seed)
• Picrotoxinine
• Unii-9K011Nuf0R
• (-)-Picrotoxinin
• Picrotoxinin

Picrotoxinin CRS

CAS: 17617-45-7

• Formula: C₁₅H₁₆O₆
• Molecular weight: 292.2839

3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-, (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-

CAS: 17617-45-7

• Formula: C₁₅H₁₆O₆
• Purity: 98%
• Color and Shape: Solid
• Molecular weight: 292.28394

Picrotoxinin

CAS: 17617-45-7

• Purity: 98.07%
• Molecular weight: 292.28g/mol

Picrotoxinin

CAS: 17617-45-7

• Formula: C₁₅H₁₆O₆
• Molecular weight: 292.28

Picrotoxinin

CAS: 17617-45-7

Lactone

• Formula: C₁₅H₁₆O₆
• Purity: ≥ 95.0 % (HPLC)
• Color and Shape: Powder
• Molecular weight: 292.29

Picrotoxinin

CAS: 17617-45-7

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• Formula: C₁₅H₁₆O₆
• Purity: Min. 95%
• Color and Shape: Powder
• Molecular weight: 292.28 g/mol

Picrotoxinin

CAS: 17617-45-7

Picrotoxinin blocks chloride channels, antagonizes GABAA noncompetitively (IC50: 1.15 μM, α1β2γ2L), and induces convulsions.

• Formula: C₁₅H₁₆O₆
• Purity: 98.07%
• Color and Shape: Solid
• Molecular weight: 292.28