Oleandrin

Oleandrin
Names
IUPAC name
16β-(Acetyloxy)-3β-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyloxy)-14-hydroxy-5β-card-20(22)-enolide
Systematic IUPAC name
(1R,2S,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a-Hydroxy-7-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-2-yl acetate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.693 Edit this at Wikidata
UNII
  • InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20+,21-,22-,23+,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1 checkY
    Key: JLPDBLFIVFSOCC-XYXFTTADSA-N checkY
  • InChI=1/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20+,21-,22-,23+,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1
    Key: JLPDBLFIVFSOCC-XYXFTTADBR
  • O=C\1OC/C(=C/1)[C@H]2[C@@H](OC(=O)C)C[C@@]6(O)[C@]2(C)CC[C@H]4[C@H]6CC[C@@H]5C[C@@H](O[C@@H]3O[C@H]([C@H](O)[C@@H](OC)C3)C)CC[C@]45C
Properties
C32H48O9
Molar mass 576.72 g/mol
Appearance Oleandrin forms colourless, odourless, acicular crystals that are very bitter
Density 1.261 g/ml
Melting point 250.0 °C (482.0 °F; 523.1 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Acute Toxicity (Oral, inhalation)
GHS labelling:
GHS06: ToxicGHS08: Health hazard
Danger
H300, H330, H373
P260, P264, P270, P271, P284, P301+P310, P304+P340, P310, P320, P330, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
0
0
Lethal dose or concentration (LD, LC):
0.248 mg/kg (Cat, Intravenous)
Safety data sheet (SDS) Safety Data Sheet
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Oleandrin is a cardiac glycoside found in the poisonous plant oleander (Nerium oleander L.).[1] As a main phytochemical of oleander, oleandrin is associated with the toxicity of oleander sap, and has similar properties to digoxin.[1]

Oleander has been used in traditional medicine for its presumed therapeutic purposes, such as for treating cardiac insufficiency. There is no clinical evidence that oleander or its constituents, including oleandrin, are safe or effective. Oleandrin is not approved by regulatory agencies as a prescription drug or dietary supplement.[1]

  1. ^ a b c "Oleander". Drugs.com. 1 December 2018. Retrieved 17 August 2020.