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C2401

Sigma-Aldrich

Crotaline

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
Beilstein/REAXYS Number:
48732
MDL number:
MFCD00084656
UNSPSC Code:
12352200
PubChem Substance ID:
24892326
NACRES:
NA.77

form

powder

mp

204 °C (dec.) (lit.)

storage temp.

2-8°C

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

InChI key

QVCMHGGNRFRMAD-XFGHUUIASA-N

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General description

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

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.

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_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

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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
Martin Connolly et al.
PloS one, 15(2), e0229409-e0229409 (2020-02-29)
The microRNA miR-1 is an important regulator of muscle phenotype including cardiac muscle. Down-regulation of miR-1 has been shown to occur in left ventricular hypertrophy but its contribution to right ventricular hypertrophy in pulmonary arterial hypertension are not known. Previous
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
Superiority of desflurane over sevoflurane and isoflurane in the presence of pressure-overload right ventricle hypertrophy in rats
Blaudszun G and Morel DR
Anesthesiology, 117(5), 1051-1061 (2012)
D W Wilson et al.
Critical reviews in toxicology, 22(5-6), 307-325 (1992-01-01)
Monocrotaline (MCT) is an 11-membered macrocyclic pyrrolizidine alkaloid (PA) that causes a pulmonary vascular syndrome in rats characterized by proliferative pulmonary vasculitis, pulmonary hypertension, and cor pulmonale. Current hypotheses of the pathogenesis of MCT-induced pneumotoxicity suggest that MCT is activated
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