Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

C2401

Sigma-Aldrich

Crotaline

Synonym(s):

(-)-Monocrotaline, Monocrotaline

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C16H23NO6
CAS Number:
315-22-0
Molecular Weight:
325.36
Beilstein:
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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Danger

Hazard Statements

H301,H351

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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
Emmy Manders et al.
American journal of physiology. Lung cellular and molecular physiology, 303(12), L1070-L1078 (2012-09-11)
We previously demonstrated that diaphragm muscle weakness is present in experimental pulmonary arterial hypertension (PH). However, the nature of this diaphragm weakness is still unknown. Therefore, the aim of this study was to investigate whether changes at the sarcomeric level
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service