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C2401

Crotaline

Name: Crotaline
Brand: SIGMA

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

Form:

powder

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Product Name

Crotaline,

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

Related Categories

Bioactive Small Molecules

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

GHS06,GHS08

signalword

Danger

hcodes

H301,H351

pcodes

P202 - P264 - P280 - P301 + P310 - P405 - P501

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

Regulatory Information

涉药品监管产品

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Integrated analysis of m6A mRNA methylation in rats with monocrotaline-induced pulmonary arterial hypertension.

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

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)

Bioinformatic analysis and validation of microRNA-508-3p as a protective predictor by targeting NR4A3/MEK axis in pulmonary arterial hypertension.

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

The monocrotaline model of pulmonary hypertension in perspective.

Jose G Gomez-Arroyo et al.

American journal of physiology. Lung cellular and molecular physiology, 302(4), L363-L369 (2011-10-04)

Severe forms of pulmonary arterial hypertension (PAH) are characterized by various degrees of remodeling of the pulmonary arterial vessels, which increases the pulmonary vascular resistance and right ventricular afterload, thus contributing to the development of right ventricle dysfunction and failure.

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Global Trade Item Number

SKU	GTIN
C2401-1G	04061833475812
C2401-500MG	04061833475829

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