Rhoeadine

Chemical compound From Wikipedia, the free encyclopedia

Rhoeadine (rheadine) is an alkaloid derived from the flowers of the corn poppy (Papaver rhoeas).[1] It has been studied for its potential use in the treatment of morphine dependence.[2]

Quick facts Names, Identifiers ...
Rhoeadine
Names
IUPAC name
8β-Methoxy-16-methyl-2′H,2′′H-bis([1,3]dioxolo)[4′,5′:2,3;4′′,5′′:10,11]rhedan
Systematic IUPAC name
(5bR,13bR,15S)-15-Methoxy-6-methyl-5b,6,7,8,13b,15-hexahydro-2H,11H-[1,3]dioxolo[4,5-h][1,3]dioxolo[4′,5′:7,8][2]benzopyrano[3,4-a][4]benzazepine
Other names
Rheadine; Rhoeadin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C21H21NO6/c1-22-6-5-11-7-15-16(26-9-25-15)8-13(11)19-18(22)12-3-4-14-20(27-10-24-14)17(12)21(23-2)28-19/h3-4,7-8,18-19,21H,5-6,9-10H2,1-2H3/t18-,19-,21+/m1/s1 checkY
    Key: XRBIHOLQAKITPP-SBHAEUEKSA-N checkY
  • InChI=1/C21H21NO6/c1-22-6-5-11-7-15-16(26-9-25-15)8-13(11)19-18(22)12-3-4-14-20(27-10-24-14)17(12)21(23-2)28-19/h3-4,7-8,18-19,21H,5-6,9-10H2,1-2H3/t18-,19-,21+/m1/s1
    Key: XRBIHOLQAKITPP-SBHAEUEKBA
  • CN1CCC2=CC3=C(C=C2[C@@H]4[C@H]1C5=C([C@H](O4)OC)C6=C(C=C5)OCO6)OCO3
Properties
C21H21NO6
Molar mass 383.400 g·mol−1
Density 1.45 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Toxicity

5 different patients were admitted to ER after being intoxicated with corn poppy. Symptoms of intoxication include nausea, vomiting, confusion, seizures, myosis and arrhythmia. These symptoms may be an outlier due to the exceptionally high dose ingested.[3]

References

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