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Merck

C2401

Crotaline

Pulmotoxic, powder

Synonym(s):

(-)-Monocrotaline, Monocrotaline

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About This Item

Empirical Formula (Hill Notation):
C16H23NO6
CAS Number:
315-22-0
Molecular Weight:
325.36
NACRES:
NA.77
PubChem Substance ID:
24892326
UNSPSC Code:
12352200
MDL number:
MFCD00084656
Beilstein/REAXYS Number:
48732

Product Name

Crotaline,

InChI key

QVCMHGGNRFRMAD-XFGHUUIASA-N

SMILES string

[H][C@@]12[C@H]3CCN1CC=C2COC(=O)[C@](C)(O)[C@](C)(O)[C@@H](C)C(=O)O3

InChI

1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1

form

powder

mp

204 °C (dec.) (lit.)

storage temp.

2-8°C

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Application

Crotaline has been used in hydrochloric acid (HCl) and injected into experimental animals to induce-pulmonary hypertension.

Biochem/physiol Actions

Crotaline induces pulmonary vascular syndrome in rats. It is considered toxic and results in hepatic cirrhosis, enlarged liver, sinusoidal obstruction syndrome and right ventricular hypertrophy.Monocrotaline is known to inhibit the growth of various experimental tumors.

General description

Crotaline is a macrocyclic compound belonging to the pyrrolizidine alkaloid family. It is naturally present in Crotalaria spectabilis.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H351

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF6577V
WXBF5510V
WXBF4230V
WXBF2954V
WXBF0845V

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Zhongkai Zhu et al.
Pulmonary circulation, 10(3), 2045894020922129-2045894020922129 (2020-09-15)
Pulmonary hypertension is a chronic vascular disease characterized by pulmonary vasoconstriction and pulmonary arterial remodeling. Pulmonary arterial remodeling is mainly due to small pulmonary arterial wall thickening and lumen occlusion. Previous studies have described intravascular changes in lung sections using
The effects of vasoactive intestinal peptide on monocrotaline induced pulmonary hypertensive rabbits following cardiopulmonary bypass: a comparative study with isoproteronol and nitroglycerine
Gunaydin S, et al.
Cardiovascular Surgery (London, England), 10(2), 138-145 (2002)
Blockade of frontocortical-brain stem pathway prevents ventricular fibrillation of ischemic heart
Skinner JE and Reed JC
American Journal of Physiology. Heart and Circulatory Physiology, 240(2), H156-H163 (1981)
Yunhong Zeng et al.
Aging, 13(14), 18238-18256 (2021-07-27)
N6-methyladenosine (m6A) modification is one of the most common chemical modifications of eukaryotic mRNAs, which play an important role in tumors and cardiovascular disease through regulating mRNA stability, splicing and translation. However, the changes of m6A mRNA and m6A-related enzymes
Yi Ma et al.
Journal of cellular and molecular medicine, 25(11), 5202-5219 (2021-05-05)
Pulmonary arterial hypertension (PAH) featured a debilitating progressive disorder. Here, we intend to determine diagnosis-valuable biomarkers for PAH and decode the fundamental mechanisms of the biological function of these markers. Two mRNA microarray profiles (GSE70456 and GSE117261) and two microRNA
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