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Merck
CN

37024

Monocrotaline

analytical standard

Synonym(s):

Crotaline, Monocrotaline

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About This Item

Empirical Formula (Hill Notation):
C16H23NO6
CAS Number:
315-22-0
Molecular Weight:
325.36
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329755589
MDL number:
MFCD00084656
Beilstein/REAXYS Number:
48732

Key Documents

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Product Name

Monocrotaline, analytical standard

SMILES string

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

InChI key

QVCMHGGNRFRMAD-XFGHUUIASA-N

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

grade

analytical standard

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

204 °C (dec.) (lit.)

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

storage temp.

−20°C

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

General description

Monocrotaline is a pyrrolizidine alkaloid that is found in plants, which belongs to the genus Crotalaria sp.

Preparation Note

Dried down, 100 μg/mL after reconstitution with 1 mL of water

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV7793

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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
Satoshi Matsuo et al.
The Journal of thoracic and cardiovascular surgery, 149(3), 902-909 (2014-12-03)
Lung ischemia-reperfusion (IR) injury during cardiopulmonary surgery is associated with postoperative morbidity and mortality, particularly in patients with pulmonary hypertension (PH). Using a rat model for monocrotaline-induced PH, we investigated the protective effect of rosuvastatin against IR injury in lungs
Edward A Pankey et al.
American journal of physiology. Heart and circulatory physiology, 305(9), H1288-H1296 (2013-09-03)
Cardiovascular responses to the tyrosine kinase inhibitor imatinib were investigated in the rat. Intravenous injections of 0.3-30 mg/kg imatinib produced small decreases in pulmonary arterial pressure, larger dose-dependent decreases in systemic arterial pressure, and no change or small increases in
Jolyane Meloche et al.
Journal of the American Heart Association, 2(1), e005157-e005157 (2013-03-26)
Pulmonary arterial hypertension (PAH) is a vasculopathy characterized by enhanced pulmonary artery smooth muscle cell (PASMC) proliferation and suppressed apoptosis. This results in both increase in pulmonary arterial pressure and pulmonary vascular resistance. Recent studies have shown the implication of
Emily A Gray et al.
Journal of synchrotron radiation, 20(Pt 5), 756-764 (2013-08-21)
Blockade of the serotonin reuptake transporter (5-HTT), using fluoxetine, has been identified as a potential therapeutic target for preventing and, importantly, reversing pulmonary hypertension (PH). This study utilized synchrotron radiation microangiography to determine whether fluoxetine could prevent or reverse endothelial
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