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Substance Name: Picrotoxin [NF]
RN: 124-87-8
UNII: ZLT174DL7U
InChIKey: VJKUPQSHOVKBCO-ZTYBEOBUSA-N

Note

  • A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.

Molecular Formula

  • C15-H18-O7.C15-H16-O6

Molecular Weight

  • 602.586
 

Classification Codes

Classification Codes

  • Antidotes
  • Central Nervous System Agents
  • Central Nervous System Stimulants
  • Convulsants
  • Drug / Therapeutic Agent
  • GABA Agents
  • GABA Antagonists
  • Human Data
  • Natural Product
  • Neurotransmitter Agents
  • Protective Agents

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 500/10000 lb
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Names and Synonyms

Name of Substance

  • Picrotoxin
  • Picrotoxin [NF]

MeSH Heading

  • Picrotoxin

Synonyms

  • 3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1aR-(1aalpha,2abeta,3beta,6beta,6abeta,8aS*,8bbeta,9S*))-, compd with (1aR-(1aalpha,2abeta,3beta,6beta,6abeta,8aS*,8bbeta,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
  • AI3-17689
  • Caswell No. 663A
  • Cocculin
  • Cocculus
  • Coques du levant
  • Coques du levant [French]
  • EINECS 204-716-6
  • EPA Pesticide Chemical Code 002301
  • Fish berry
  • HSDB 6385
  • Indian berry
  • NSC 403139
  • Oriental berry
  • Picrotin, compd. with picrotoxinin (1:1)
  • Picrotin, compound with picrotoxinin (1:1)
  • Picrotox
  • Picrotoxin
  • Picrotoxine
  • Picrotoxinin - picrotin
  • Picrotoxinin, compd. with picrotin (1:1)
  • Picrotoxinum
  • UNII-ZLT174DL7U

Systematic Names

  • 3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1aR,2aR,3S,6R,6aS,8aS,8bR,9S)-, compd. with (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 (1:1)
  • 3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1aR-(1aalpha,2abeta,3beta,6beta,6abeta,8aS*,8bbeta,9S*))-, compd. with (1aR-(1aalpha,2abeta,3beta,6beta,6abeta,8aS*,8bbeta,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 (1:1)
  • Picrotoxin

Superlist Names

  • Cocculus
  • Picrotoxin

Registry Numbers

CAS Registry Number

  • 124-87-8

FDA UNII

  • ZLT174DL7U

System Generated Number

  • 0000124878

Molecular Formulas

Molecular Formula

  • C15-H18-O7.C15-H16-O6

Molecular Formula Fragments

  • C15-H16-O6
  • C15-H18-O7
  • COMPONENT

Structure Descriptors

InChI

1S/C15H18O7.C15H16O6/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;1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h5-9,18-19H,4H2,1-3H3;6-10,18H,1,4H2,2-3H3/t5-,6+,7?,8?,9-,13-,14-,15+;6?,7-,8?,9?,10+,13+,14+,15-/m10/s1

InChIKey

VJKUPQSHOVKBCO-ZTYBEOBUSA-N

Smiles

O1[C@H]2[C@@]31[C@@]1([C@@](C2)([C@@H]2[C@H](C(C)(C)O)[C@@H]([C@H]1OC3=O)OC2=O)O)C.O1[C@@]23[C@@]4([C@@]([C@@H]5[C@H](C(C)=C)[C@@H]([C@H]4OC3=O)OC5=O)(O)C[C@@H]12)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intracrebral 25ug/kg (0.025mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 9, 1962.
cat LDLo oral 1750ug/kg (1.75mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1385, 1935.
cat LDLo subcutaneous 2mg/kg (2mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1385, 1935.
dog LDLo intramuscular 1mg/kg (1mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1385, 1935.
dog LDLo subcutaneous 1500ug/kg (1.5mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1385, 1935.
frog LDLo intramuscular 2mg/kg (2mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1385, 1935.
frog LDLo parenteral 20mg/kg (20mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932.
frog LDLo subcutaneous 2mg/kg (2mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
guinea pig LDLo subcutaneous 300ug/kg (0.3mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1385, 1935.
human LDLo oral 357ug/kg (0.357mg/kg) GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 476, 1969.
man LDLo unreported 1471ug/kg (1.471mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 9200ug/kg (9.2mg/kg)   United States Patent Document. Vol. #3749765,
mouse LD50 intravenous 2440ug/kg (2.44mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 9, 1962.
mouse LD50 oral 15mg/kg (15mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: TREMOR
Journal of Pharmacology and Experimental Therapeutics. Vol. 128, Pg. 176, 1960.
mouse LD50 subcutaneous 4100ug/kg (4.1mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: REGIDITY

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 1, Pg. 423, 1964.
mouse LD50 unreported 4120ug/kg (4.12mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 2S, 1957.
mouse LDLo intracrebral 5ug/kg (0.005mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Research Communications in Chemical Pathology and Pharmacology. Vol. 39, Pg. 367, 1983.
pigeon LDLo intramuscular 1400ug/kg (1.4mg/kg)   Journal of the American Pharmaceutical Association. Vol. 23, Pg. 98, 1934.
pigeon LDLo subcutaneous 1400ug/kg (1.4mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rabbit LD50 intravenous 1016ug/kg (1.016mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 2, 1940.
rabbit LDLo oral 2500ug/kg (2.5mg/kg)   Journal of the American Pharmaceutical Association. Vol. 23, Pg. 98, 1934.
rabbit LDLo subcutaneous 1300ug/kg (1.3mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rat LD50 intraperitoneal 1990ug/kg (1.99mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 14, Pg. 996, 1964.
rat LD50 intravenous 1600ug/kg (1.6mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 14, Pg. 996, 1964.
rat LD50 subcutaneous 2880ug/kg (2.88mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 38, Pg. 604, 1949.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 203.5 deg C   EXP
log P (octanol-water) -2.810 (none)   EST
Water Solubility 4100 mg/L   EXP
Vapor Pressure 1.08E-11 mm Hg 25 EST
Henry's Law Constant 3.12E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.99E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.