CAS 124-87-8|Picrotoxin

Introduction：Basic information about CAS 124-87-8|Picrotoxin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Picrotoxin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles114
7. Synonyms

Common Name	Picrotoxin
CAS Number	124-87-8	Molecular Weight	301.29
Density	/	Boiling Point	/
Molecular Formula	C₁₅H₁₈O_7.C₁₅H₁₆O₆	Melting Point	203 â„ƒ(lit.)
MSDS	ChineseUSA	Flash Point	/
Symbol	GHS06	Signal Word	Danger

Names

Name	Picrotoxin,1:1mixtureofpicrotoxininandpicrotin
Synonym	More Synonyms

Picrotoxin BiologicalActivity

Description	Picrotoxin is a noncompetitive antagonist of GABAA receptor.
Related Catalog	Signaling Pathways >>Membrane Transporter/Ion Channel >>GABA ReceptorSignaling Pathways >>Neuronal Signaling >>GABA ReceptorResearch Areas >>Neurological DiseaseNatural 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.

Chemical & Physical Properties

Melting Point	203 â„ƒ(lit.)
Molecular Formula	C₁₅H₁₈O_7.C₁₅H₁₆O₆
Molecular Weight	301.29
PSA	190.95000
InChIKey	VJKUPQSHOVKBCO-UHFFFAOYSA-N
SMILES	C=C(C)C1C2OC(=O)C1C1(O)CC3OC34C(=O)OC2C14C.CC(C)(O)C1C2OC(=O)C1C1(O)CC3OC34C(=O)OC2C14C
Storage condition	-20°C

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

Articles114

Frequency-dependent, cell type-divergent signaling in the hippocamposeptal projection.

J. Neurosci. 34(35) , 11769-80, (2014)

Hippocampal oscillations are critical for information processing, and are strongly influenced by inputs from the medial septum. Hippocamposeptal neurons provide direct inhibitory feedback from the hip...

Parallel ON and OFF cone bipolar inputs establish spatially coextensive receptive field structure of blue-yellow ganglion cells in primate retina.

J. Mol. Endocrinol. 29 , 8372-87, (2009)

In the primate retina the small bistratified, "blue-yellow" color-opponent ganglion cell receives parallel ON-depolarizing and OFF-hyperpolarizing inputs from short (S)-wavelength sensitive and combin...

Modifications of diflunisal and meclofenamate carboxyl groups affect their allosteric effects on GABAA receptor ligand binding.

Neurochem. Res. 39(7) , 1183-91, (2014)

Gamma-aminobutyric acid type A receptors (GABAAR) are allosterically modulated by the nonsteroidal anti-inflammatory drugs diflunisal and fenamates. The carboxyl group of these compounds is charged at...

Synonyms

(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

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