Crotaline

Modify Date: 2024-01-02 14:27:13

Crotaline Structure
Crotaline structure
 Common Name Crotaline
CAS Number 315-22-0 Molecular Weight 325.357
Density 1.4±0.1 g/cm3 Boiling Point 537.3±50.0 °C at 760 mmHg
Molecular Formula C16H23NO6 Melting Point 204ºC (dec.)(lit.)
MSDS Chinese USA Flash Point 278.7±30.1 °C
Symbol GHS06 GHS08
GHS06, GHS08		 Signal Word Danger

 Use of Crotaline


Monocrotaline is an pyrrolizidine alkaloid extracted from the seeds of the Crotalaria spectabilis plant to induce pulmonary hypertension in rodents.

 Names

Name monocrotaline
Synonym More Synonyms

 Crotaline Biological Activity

Description Monocrotaline is an pyrrolizidine alkaloid extracted from the seeds of the Crotalaria spectabilis plant to induce pulmonary hypertension in rodents.
Related Catalog
In Vitro Monocrotaline (MCT) is an 11-membered macrocyclic pyrrolizidine alkaloid (PA) derived from the seeds of the Crotalaria spectabilis plant[1]. Monocrotaline a natural ligand exhibits dose-dependent cytotoxicity with potent antineoplastic activity. The in vitro cytotoxicity of monocrotaline is proved at IC50 24.966 µg/mL and genotoxicity at 2 X IC50 against HepG2 cells[2].
In Vivo MCT causes a pulmonary vascular syndrome in rats characterized by proliferative pulmonary vasculitis, pulmonary hypertension (PH), and cor pulmonale[3]. Among preclinical models of pulmonary arterial hypertension (PAH), monocrotaline animal model offers the advantage of mimic several key aspects of human PAH, including vascular remodeling, proliferation of smooth muscle cells, endothelial dysfunction, upregulation of inflammatory cytokines, and right ventricle failure, requiring a single drug injection[4]. Changes in multiple pathways associated with the development of PH, including activated glycolysis, increased markers of proliferation, disruptions in carnitine homeostasis, increased inflammatory and fibrosis biomarkers, and a reduction in glutathione biosynthesis are observed with the injection of monocrotaline[5].
Animal Admin Rats: A total of 20 male Sprague Dawley rats (SD; 220-270g) are used in this study (n=10 per group). Control group received vehicle for monocrotaline (MCT). Pre-pulmonary hypertension (PH) group received a single injection of MCT (60 mg/kg i.p.) to induce and are sacrificed after 14 days[5].
References

[1]. Gomez-Arroyo JG, et al. The monocrotaline model of pulmonary hypertension in perspective. Am J Physiol Lung Cell Mol Physiol. 2012 Feb 15;302(4):L363-9.

[2]. Kusuma SS, et al. Antineoplastic activity of monocrotaline against hepatocellular carcinoma. Anticancer Agents Med Chem. 2014;14(9):1237-48.

[3]. Wilson DW, et, al. Mechanisms and pathology of monocrotaline pulmonary toxicity. Crit Rev Toxicol. 1992;22(5-6):307-25.

[4]. Nogueira-Ferreira R, et al. Exploring the monocrotaline animal model for the study of pulmonary arterial hypertension: A network approach. Pulm Pharmacol Ther. 2015 Dec;35:8-16.

[5]. Rafikova O,et al. Metabolic Changes Precede the Development of Pulmonary Hypertension in the Monocrotaline Exposed RatLung. PLoS One. 2016 Mar 3;11(3):e0150480.

 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

 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
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

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 Synonyms

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
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