Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H18O7 |
Molecular Weight | 310.2992 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12OC(=O)[C@@]34O[C@@H]3C[C@@](O)([C@@H]5[C@@H]([C@H]1OC5=O)C(C)(C)O)[C@@]24C
InChI
InChIKey=RYEFFICCPKWYML-QCGISDTRSA-N
InChI=1S/C15H18O7/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/h5-9,18-19H,4H2,1-3H3/t5-,6+,7-,8-,9-,13-,14-,15+/m1/s1
Picrotin is a component of picrotoxin, an equimolar mixture of picrotoxinin and picrotin, which was isolated from the fruit of Anamirta cocculus. Picrotin is inactive in inhibiting the GABA-A and GABA-C receptors, but the compound is able to block homomeric alpha1 and alpha1 beta glycine receptors. Picrotoxin is used as an antidote to severe barbiturate poisoning, however picrotin does not participate in the activity. Picrotin is not toxic.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P23415 Gene ID: 2741.0 Gene Symbol: GLRA1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17714449 |
5.2 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
---|---|---|
Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors. | 2007 Jun 1 |
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A proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore. | 2007 Oct |
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Ginkgolide B and bilobalide block the pore of the 5-HT₃receptor at a location that overlaps the picrotoxin binding site. | 2011 Feb-Mar |
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NCI_THESAURUS |
C47795
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21416-53-5
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U06Z6QD7N2
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2163
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129536
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C87696
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m8796
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442291
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DTXSID80274161
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SUBSTANCE RECORD