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Substance Name: Picrotoxinin
RN: 17617-45-7
UNII: 9K011NUF0R
InChIKey: PIMZUZSSNYHVCU-YKWPQBAZSA-N

Note

  • Toxic component of picrotoxin; noncompetitive antagonist of ionotropic GABA-A receptors.

Molecular Formula

  • C15-H16-O6

Molecular Weight

  • 292.2854
 

Classification Codes

  • GABA Agents
  • GABA Antagonists
  • GABA-A Receptor Antagonists
  • Neurotransmitter Agents
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Names and Synonyms

Name of Substance

  • Picrotoxinin

Synonyms

  • AI3-41571
  • NSC 129537
  • Picrotoxinin
  • Picrotoxinine
  • UNII-9K011NUF0R

Systematic Names

  • (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
  • 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*))-
  • Picrotoxinin (from Anamirta cocculus seed)

Registry Numbers

CAS Registry Number

  • 17617-45-7

FDA UNII

  • 9K011NUF0R

System Generated Number

  • 0017617457

Structure Descriptors

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

InChIKey

PIMZUZSSNYHVCU-YKWPQBAZSA-N

Smiles

[C@@]123C(=O)O[C@H]4[C@@]1([C@]([C@H]1C(=O)O[C@@H]4[C@H]1C(=C)C)(C[C@H]2O3)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo subcutaneous 1100ug/kg (1.1mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
frog LDLo subcutaneous 1100ug/kg (1.1mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
mouse LD50 intracrebral 10ug/kg (0.01mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Toxicology Letters. Vol. 60, Pg. 289, 1992.
mouse LD50 intraperitoneal 8980ug/kg (8.98mg/kg)   Current Toxicology. Vol. 1, Pg. 199, 1993.
mouse LDLo subcutaneous 1600ug/kg (1.6mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of the American Pharmaceutical Association. Vol. 23, Pg. 98, 1934.
pigeon LDLo intramuscular 1600ug/kg (1.6mg/kg)   Journal of the American Pharmaceutical Association. Vol. 23, Pg. 98, 1934.
pigeon LDLo subcutaneous 1600ug/kg (1.6mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rabbit LDLo subcutaneous 1350ug/kg (1.35mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.