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Monocrotaline information


Monocrotaline
Skeleton formula of a carbon ring, containing oxygen, hydrogen and nitrogen atoms. It is supposed to be monocrotaline
Chemical structure of monocrotaline
Names
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
Other names
  • Crotaline
  • (-)-Monocrotaline
  • Retronecine cyclic 2,3-dihydroxy-2,3,4-trimethylglutarate
Identifiers
3DMet
  • 315-22-0
ChEBI
  • CHEBI:6980
ECHA InfoCard 100.156.772 Edit this at Wikidata
PubChem CID
  • 9415
UNII
  • 73077K8HYV
CompTox Dashboard (EPA)
  • DTXSID9020902 Edit this at Wikidata
Properties
Chemical formula
C16H23NO6
Molar mass 325.361 g·mol−1
Appearance Crystalline solid
Melting point 204 °C (399 °F; 477 K)
Solubility in water
Slightly soluble
Hazards
GHS labelling:
Pictograms
GHS06: Toxic GHS08: Health hazard
Hazard statements
H301, H351
Precautionary statements
P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, P501
Lethal dose or concentration (LD, LC):
LD50 (median dose)
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).
Infobox references

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.

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Monocrotaline

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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...

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Crotalaria

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pyrrolizidine alkaloids that are found in Crotalaria plants are monocrotaline and spectabiline. Monocrotaline is most toxic to the pulmonary vasculature and is used...

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IARC group 2B

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Mitoxantrone Molybdenum trioxide 3-Monochloro-1,2-propanediol (3-MCPD) Monocrotaline 5-(Morpholinomethyl)-3-[(5-nitrofurfurylidene)amino]-2-oxazolidinone...

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Methylsulfonylmethane

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effects of methylsulfonylmethane on hemodynamics and oxidative stress in monocrotaline-induced pulmonary hypertensive rats". Advances in Pharmacological Sciences...

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Minocycline

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(June 2018). "Involvement of Neuroinflammation in the Pathogenesis of Monocrotaline-Induced Pulmonary Hypertension". Hypertension. 71 (6): 1156–1163. doi:10...

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Pyrrolizidine alkaloid

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in differences in toxicity. For example, retronecine-type PAs like monocrotaline are known to be highly hepatotoxic, while other types may exhibit lower...

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California Proposition 65 list of chemicals

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(furilazole) 121776-33-8 3-Monochloropropane-1,2-diol (3-MCDP) 96-24-2 Monocrotaline 315-22-0 MOPP (vincristine-prednisone-nitrogen mustard-procarbazine...

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Crotalaria cunninghamii

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known to contain pyrrolizidine alkaloids, the most potent of which are monocrotaline, retrorsine and retronecine. Pyrrolizidine alkaloids are found in 3%...

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Simmerafil

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List of compounds with carbon number 16

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C16H23NO2 piperocaine 136-82-3 C16H23NO2 properidine 561-76-2 C16H23NO6 monocrotaline 315-22-0 C16H23N3OS buprofezin 69327-76-0 C16H24N2 isoaminile 77-51-0...

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Pyrrolizidine alkaloidosis

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ranges from moderate to severe, as well as damage to other organs. Monocrotaline specifically causes pulmonary arterial hypertension. The longevity of...

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Enantiostasis

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Guanidinoethane Sulfonate on Toxicity of the Pyrrolizidine Alkaloid Monocrotaline". Biochemical Pharmacology. 51 (3): 321–329. doi:10.1016/0006-2952(95)02185-X...

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