Monocrotaline

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.156.772 Edit this at Wikidata
EC Number
  • 628-506-2
KEGG
UNII
  • 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
    Key: QVCMHGGNRFRMAD-XFGHUUIASA-N
  • C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O
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:
GHS06: Toxic GHS08: Health hazard
H301, H351
P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, P501
Lethal dose or concentration (LD, LC):
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).

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.