Cas no 17617-45-7 (Picrotoxinin)

Picrotoxinin is a sesquiterpene lactone derived from the seeds of Anamirta cocculus and related plants. It acts as a noncompetitive antagonist of GABA_A receptors, selectively blocking chloride channels and inducing convulsant activity. This compound is widely utilized in neuroscience research to study inhibitory neurotransmission and GABAergic mechanisms. Its high specificity and potency make it a valuable tool for investigating synaptic inhibition, epilepsy models, and receptor pharmacology. Picrotoxinin is also employed in electrophysiological studies to elucidate the role of GABA in neural circuits. Available in high-purity forms, it ensures reliable and reproducible experimental results in both in vitro and in vivo applications.
Picrotoxinin structure
Picrotoxinin structure
Product Name:Picrotoxinin
CAS No:17617-45-7
MF:C15H16O6
MW:292.283945083618
MDL:MFCD00078765
CID:156586
Update Time:2025-07-22

Picrotoxinin Chemical and Physical Properties

Names and Identifiers

    • 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)-
    • Picrotoxinin
    • 3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione,hexahydro-2a-hydrox...
    • 3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione,hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)
    • PICROTOXININ(RG)
    • Yellowmouth Dutchmanspipe Root
    • ahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-,(1ar-(1a-alpha,2a-beta,3-bet
    • 6a-beta,8as*,8b-beta,9r*))-6-beta
    • MDL: MFCD00078765
    • 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: PIMZUZSSNYHVCU-YKWPQBAZSA-N
    • SMILES: O1[C@@H]2C[C@]3([C@H]4C(=O)O[C@H]([C@H]4C(=C)C)[C@@H]4[C@@]3(C)[C@]12C(=O)O4)O

Computed Properties

  • Exact Mass: 292.09500
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 1
  • Complexity: 642
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 8
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • XLogP3: -0.5
  • Topological Polar Surface Area: 85.4

Experimental Properties

  • Color/Form: Uncertain
  • Density: 1.2207 (rough estimate)
  • Melting Point: 203-205°C
  • Boiling Point: 354.22°C (rough estimate)
  • Refractive Index: 1.4359 (estimate)
  • PSA: 85.36000
  • LogP: -0.06200
  • Solubility: Uncertain
  • Specific Rotation: D17 +4.4° (c = 4.28 in abs alc), +3.49° (c = 7.57 in acetone)

Picrotoxinin Security Information

  • Hazardous Material transportation number:UN 3172
  • Hazard Category Code: 25-28
  • Safety Instruction: 13-20-45-36/37-28
  • RTECS:PC5150000
  • Hazardous Material Identification: T+
  • Safety Term:6.1(a)
  • Risk Phrases:R25; R28
  • HazardClass:6.1(a)
  • PackingGroup:I
  • Toxicity:LD50 i.p. in mice: 3 mg/kg (Jarboe)
  • Hazard Level:6.1(a)

Picrotoxinin Pricemore >>

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Picrotoxinin Related Literature

Additional information on Picrotoxinin

Picrotoxinin: A Comprehensive Overview

Picrotoxinin, also known as CAS No. 17617-45-7, is a naturally occurring compound that has garnered significant attention in the fields of pharmacology and toxicology. This compound is primarily found in certain plant species and has been extensively studied for its biological activities and potential applications in medicine and research.

Picrotoxinin is a sesquiterpenoid lactone, a class of compounds known for their diverse biological properties. Its chemical structure, characterized by a unique arrangement of oxygen atoms and a lactone ring, contributes to its potent pharmacological effects. Recent studies have highlighted its role as a neurotoxin, particularly in its ability to induce seizures in experimental models. This property has led researchers to explore its mechanisms of action and potential therapeutic uses.

One of the most notable aspects of Picrotoxinin is its interaction with ion channels, particularly the GABAA receptor complex. Studies have shown that it enhances the activity of GABAA receptors, leading to increased chloride ion influx into neurons. This effect has been linked to its convulsant properties, as excessive neuronal excitation can trigger seizures. However, this same mechanism has also raised interest in its potential use as a tool for studying epilepsy and other neurological disorders.

Recent advancements in analytical techniques have allowed for a deeper understanding of Picrotoxinin's pharmacokinetics and metabolism. Researchers have identified key enzymes involved in its biotransformation, shedding light on how it is processed within the body. This knowledge is crucial for developing strategies to mitigate its toxic effects while maximizing its therapeutic potential.

In terms of applications, Picrotoxinin has been utilized as a research tool in neuropharmacology due to its ability to modulate neuronal activity. It has been employed in preclinical studies to investigate the pathophysiology of epilepsy and other seizure-related conditions. Additionally, its unique chemical structure makes it a valuable compound for drug discovery efforts aimed at developing novel antiepileptic agents.

Despite its promising applications, the toxicity profile of Picrotoxinin remains a critical area of investigation. Studies have demonstrated that it can cause adverse effects at higher doses, including neurotoxicity and hepatotoxicity. Understanding these effects is essential for ensuring safe use in both research and clinical settings.

Recent collaborative efforts between academic institutions and pharmaceutical companies have led to breakthroughs in synthesizing analogs of Picrotoxinin with improved safety profiles. These analogs are being tested for their efficacy in treating refractory epilepsy, a condition that currently lacks effective treatment options.

In conclusion, Picrotoxinin (CAS No. 17617-45-7) is a compound with significant scientific and therapeutic potential. Its unique pharmacological properties, coupled with ongoing research advancements, position it as a key player in the development of novel treatments for neurological disorders. As our understanding of this compound continues to grow, so too does its promise as a valuable tool in medicine and neuroscience.

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