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PICROTOXININ

CAS No.
17617-45-7
Chemical Name:
PICROTOXININ
Synonyms
PICROTOXININ;Picrotoxinin CRS;PICROTOXININ USP/EP/BP;Yellowmouth Dutchmanspipe Root;6a-beta,8as*,8b-beta,9r*))-6-beta;ahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-,(1ar-(1a-alpha,2a-beta,3-bet;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)-
CBNumber:
CB7420980
Molecular Formula:
C15H16O6
Molecular Weight:
292.28
MDL Number:
MFCD00078765
MOL File:
17617-45-7.mol
MSDS File:
SDS
Last updated:2023-05-25 18:01:17

PICROTOXININ Properties

Melting point 203-205°C
alpha D17 +4.4° (c = 4.28 in abs alc), +3.49° (c = 7.57 in acetone)
Boiling point 354.22°C (rough estimate)
Density 1.2207 (rough estimate)
refractive index 1.4359 (estimate)
storage temp. 2-8°C
pka 13.18±0.60(Predicted)
LogP -0.130 (est)
FDA UNII 9K011NUF0R
EPA Substance Registry System Picrotoxinin (17617-45-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300
Precautionary statements  P301+P310+P330
Hazard Codes  T+
Risk Statements  25-28
Safety Statements  13-20-45-36/37-28
RIDADR  3172
WGK Germany  3
RTECS  PC5150000
HazardClass  6.1(a)
PackingGroup  I
Toxicity LD50 i.p. in mice: 3 mg/kg (Jarboe)

PICROTOXININ price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Y0001528 Picrotoxinin European Pharmacopoeia (EP) Reference Standard 17617-45-7 y0001528 $220 2024-03-01 Buy
Sigma-Aldrich P8390 Picrotoxinin 17617-45-7 250mg $229 2024-03-01 Buy
Sigma-Aldrich PHL80339 Picrotoxinin phyproof? Reference Substance 17617-45-7 20mg $344 2024-03-01 Buy
TRC P437633 Picrotoxinin 17617-45-7 500mg $210 2021-12-16 Buy
TRC P437633 Picrotoxinin 17617-45-7 250mg $130 2021-12-16 Buy
Product number Packaging Price Buy
Y0001528 y0001528 $220 Buy
P8390 250mg $229 Buy
PHL80339 20mg $344 Buy
P437633 500mg $210 Buy
P437633 250mg $130 Buy

PICROTOXININ Chemical Properties,Uses,Production

Uses

Picrotoxinin is a L-glutamate and channel blockers.

Definition

ChEBI: Picrotoxinin is a picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone gamma-lactone formation by O-alkylation to positions 4 and 5, respectively. A component of picrotoxin. It has a role as a plant metabolite, a GABA antagonist and a serotonergic antagonist. It is an organic heteropentacyclic compound, an epoxide, a tertiary alcohol, a gamma-lactone and a picrotoxane sesquiterpenoid.

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.

172172-74-6
17617-45-7
Synthesis of PICROTOXININ from Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

PICROTOXININ Preparation Products And Raw materials

Raw materials

Preparation Products

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6a-beta,8as*,8b-beta,9r*))-6-beta ahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-,(1ar-(1a-alpha,2a-beta,3-bet PICROTOXININ Yellowmouth Dutchmanspipe Root Picrotoxinin CRS 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 USP/EP/BP 17617-45-7 C15H16O6 C15H16O6H2O GABAA receptor antagonist; binds to the GABA receptor-linked Cl- channel. Cell Signaling and Neuroscience Cell Biology BioChemical Ligand-Gated Ion Channels Ion Channels GABA and Glycine Receptor Modulators Miscellaneous Natural Products AntagonistsIon Channels GABA and Glycine Receptor Modulators GABAergics Ligand-Gated Ion Channels Neurotransmitters