Crotaline

Suppliers

Names

[ CAS No. ]:
315-22-0

[ Name ]:
Crotaline

[Synonym ]:
Monocrotaline/crotaline
Monccrotalire
Bulbus Lilii
CROTALINE
(13a,14a)-14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
Monocrotaline
2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-
(3R,4R,5R,13aR,13bR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
MONOCRATALINE
MFCD00084656
A 6080
MONOCROTALIN
CROTALIN
Crotaline,Monocrotaline

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
537.3±50.0 °C at 760 mmHg

[ Melting Point ]:
204ºC (dec.)(lit.)

[ Molecular Formula ]:
C₁₆H₂₃NO₆

[ Molecular Weight ]:
325.357

[ Flash Point ]:
278.7±30.1 °C

[ Exact Mass ]:
325.152527

[ PSA ]:
96.30000

[ LogP ]:
-0.37

[ Vapour Pressure ]:
0.0±3.2 mmHg at 25°C

[ Index of Refraction ]:
1.586

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QB3140000

CHEMICAL NAME :: Monocrotaline

CAS REGISTRY NUMBER :: 315-22-0

BEILSTEIN REFERENCE NO. :: 0048732

LAST UPDATED :: 199612

DATA ITEMS CITED :: 44

MOLECULAR FORMULA :: C16-H23-N-O6

MOLECULAR WEIGHT :: 325.40

WISWESSER LINE NOTATION :: T55 AN CUTJ FQ D1OV1- ET5OVTJ C1 D1 EQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 66 mg/kg

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), diffuse

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 130 mg/kg

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

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 92 mg/kg

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

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 60 mg/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 259 mg/kg

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

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 261 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 60 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 61600 ug/kg/28D-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - changes in lung weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other oxidoreductases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 18 mg/kg/10D-C

TOXIC EFFECTS :: Cardiac - changes in heart weight Lungs, Thorax, or Respiration - changes in lung weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 75600 ug/kg/3W-C

TOXIC EFFECTS :: Vascular - BP elevation not characterized in autonomic section Lungs, Thorax, or Respiration - changes in lung weight Cardiac - changes in heart weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 288 mg/kg/48W-I

TOXIC EFFECTS :: Vascular - thrombosis distant from injection site Blood - hemorrhage Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1050 mg/kg/14D-I

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - changes in spleen weight Blood - changes in leukocyte (WBC) count

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 130 mg/kg/1Y-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors Liver - tumors

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Heritable translocation test

TYPE OF TEST :: DNA damage

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Mammal - species unspecified Leukocyte

DOSE/DURATION :: 25 umol/L

REFERENCE :: CYTBAI Cytobios. (Faculty Press, 88 Regent St., Cambridge, UK) V.1- 1969- Volume(issue)/page/year: 14,151,1975 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,291,1976 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,291,1976 IARC Cancer Review:Group 2B IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 35,89,1976 TOXICOLOGY REVIEW CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,1171,1976

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H351

[ Precautionary Statements ]:
P281-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: Toxic;

[ Risk Phrases ]:
R25

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

[ RIDADR ]:
UN 1544 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
QB3140000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
29399990

Precursor & DownStream

Precursor

monocrotaline methylene acetal
(13R,14R)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione 4-oxide
(4R,5S)-2-(trimethylsilyl)ethyl 5-((R)-1-(((1R,7aR)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl)oxy)-1-oxopropan-2-yl)-4,5-dimethyl-1,3-dioxolane-4-carboxylate
(4R,5S)-2-(trimethylsilyl)ethyl 5-((R)-1-(((1R,7aR)-7-(((tert-butyldimethylsilyl)oxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl)oxy)-1-oxopropan-2-yl)-4,5-dimethyl-1,3-dioxolane-4-carboxylate
(2R,3R,4R)-2,3,4-trimethyl-2,3-methylenedioxypentanedioic anhydride
(2R,3R,4R)-2,3,4-Trimethyl-2,3-(methylenedioxy)pentanedioic acid
(2'R,3R,4S)-5-[2'-methoxy-2'-(trifluoromethyl)phenylacetoxy]-2,3,4-trimethyl-3,4-methylenedioxy-2-pentene
(2'R,2S,3R,4S)-5-[2'-methoxy-2'-(trifluoromethyl)phenylacetoxy]-2,3,4-trimethyl-3,4-methylenedioxypentanoic acid

DownStream

DEHYDRORETRONECINE
Dehydromonocrotaline
Butanedioic acid,2,3-dimethyl-, (2R,3S)-rel-
(13R,14R)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione 4-oxide
Spectabiline
(12R,13R,14R)-12,13-Bis(acetoxy)-14,19-dihydro-20-norcrotalanan-11,15-dione
2,3-dimethyl-4-oxopentanoic acid
Retronecine

Articles

The Japanese toxicogenomics project: application of toxicogenomics.

Mol. Nutr. Food. Res. 54 , 218-27, (2010)

Biotechnology advances have provided novel methods for the risk assessment of chemicals. The application of microarray technologies to toxicology, known as toxicogenomics, is becoming an accepted appr...

Developing structure-activity relationships for the prediction of hepatotoxicity.

Chem. Res. Toxicol. 23 , 1215-22, (2010)

Drug-induced liver injury is a major issue of concern and has led to the withdrawal of a significant number of marketed drugs. An understanding of structure-activity relationships (SARs) of chemicals ...

A predictive ligand-based Bayesian model for human drug-induced liver injury.

Drug Metab. Dispos. 38 , 2302-8, (2010)

Drug-induced liver injury (DILI) is one of the most important reasons for drug development failure at both preapproval and postapproval stages. There has been increased interest in developing predicti...