Picrotoxin

Names

[ CAS No. ]:
124-87-8

[ Name ]:
Picrotoxin

[Synonym ]:
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tetradecane-6,11-dione - (1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tetradecane-6,11-dione (1:1)
Picrotox
EINECS 204-716-6
PICROTOXIN
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)-, compd. with (1aR,2aR,3S,6R,6aS,8aS,8bR,9S)-hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-3,6-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione (1:1)
fishberry
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-14-isopropenyl-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tetradecan-6,11-dion--(1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxy-2-propanyl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tetradecan-6,11-dion(1:1)
indianberry
Picrotin - Picrotoxinin
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-13-méthyl-14-(1-propèn-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tétradécane-6,11-dione - (1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxy-2-propanyl)-13-méthyl-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tétradécane-6,11-dione (1:1)
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-14-isopropenyl-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tetradecane-6,11-dione - (1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxy-2-propanyl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tetradecane-6,11-dione (1:1)
picrotoxine
MFCD00074824
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-14-isopropenyl-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tetradecane-6,11-dione - (1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxy-2-pro panyl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1.0.0]tetradecane-6,11-dione (1:1)
COCCULIN
COCCULINE
Cocculus

Biological Activity

[Description]:

Picrotoxin is a noncompetitive antagonist of GABAA receptor.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Research Areas >> Neurological Disease

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Boulanger JJ, et al. Oligodendrocyte progenitor cells are paired with GABA neurons in the mouse dorsal cortex: Unbiased stereological analysis. Neuroscience. 2017 Aug 18. pii: S0306-4522(17)30584-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
203 â„ƒ(lit.)

[ Molecular Formula ]:
C₁₅H₁₈O_7.C₁₅H₁₆O₆

[ Molecular Weight ]:
301.29

[ PSA ]:
190.95000

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TJ9100000

CHEMICAL NAME :: Picrotoxin

CAS REGISTRY NUMBER :: 124-87-8

LAST UPDATED :: 199703

DATA ITEMS CITED :: 26

MOLECULAR FORMULA :: C15-H18-O7.C15-H16-O6

MOLECULAR WEIGHT :: 602.64

WISWESSER LINE NOTATION :: T D3556 J5 K 2AF N EOXVO MVO DH&TTTTJ A1 BQ KY1&U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 357 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - excitement Gastrointestinal - other changes

REFERENCE :: 34ZIAG "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969 Volume(issue)/page/year: -,476,1969

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1471 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85DCAI "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970 Volume(issue)/page/year: 2,73,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1990 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 14,996,1964

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2880 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 38,604,1949

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1600 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 14,996,1964

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - excitement

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 128,176,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 9200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3749765

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4100 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Behavioral - rigidity (including catalepsy)

REFERENCE :: RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 1,423,1964

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2440 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 135,9,1962

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 39,367,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4120 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 53,2S,1957

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1385,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1385,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 1750 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1385,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1385,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 25 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 135,9,1962

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPHAA3 Journal of the American Pharmaceutical Association. (Washington, DC) V.1-28, 1912-39; New series: V.1-17, 1961-77. Volume(issue)/page/year: 23,98,1934

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1300 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1016 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 29,2,1940

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 300 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1385,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Bird - pigeon

DOSE/DURATION :: 1400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Bird - pigeon

DOSE/DURATION :: 1400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPHAA3 Journal of the American Pharmaceutical Association. (Washington, DC) V.1-28, 1912-39; New series: V.1-17, 1961-77. Volume(issue)/page/year: 23,98,1934

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1385,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold Cardiac - other changes

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 166,437,1932 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 42 mg/kg/3W-I

TOXIC EFFECTS :: Musculoskeletal - other changes Nutritional and Gross Metabolic - changes in calcium Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

REFERENCE :: JCGBDF Journal of Craniofacial Genetics and Developmental Biology. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 8,351,1988

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+;N

[ Risk Phrases ]:
28-52/53

[ Safety Phrases ]:
28-36/37/39-45-61

[ RIDADR ]:
UN 3462 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
TJ9100000

[ Packaging Group ]:
I

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