Chemical structure of monocrotaline
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Names | |
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IUPAC name
(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
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Other names
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.156.772 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C16H23NO6 | |
Molar mass | 325.361 g·mol−1 |
Appearance | Crystalline solid |
Melting point | 204 °C (399 °F; 477 K) |
Slightly soluble | |
Hazards | |
GHS labelling: | |
H301, H351 | |
P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, P501 | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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66 mg/kg (rat, oral) / 259 mg/kg (mouse) intravenous) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Monocrotaline (MCT) is a pyrrolizidine alkaloid that is present in plants of the Crotalaria genus. These species can synthesise MCT out of amino acids and can cause liver, lung and kidney damage in various organisms. Initial stress factors are released intracellular upon binding of MCT to BMPR2 receptors and elevated MAPK phosphorylation levels are induced, which can cause cancer in Homo sapiens. MCT can be detoxified in rats via oxidation, followed by glutathione-conjugation and hydrolysis.