Rhoeadine

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
CAS Number
  • 2718-25-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:8836
ChemSpider
  • 171184 checkY
KEGG
  • C09619 ☒N
PubChem CID
  • 197775
UNII
  • 9Q9C65WH3B checkY
CompTox Dashboard (EPA)
  • DTXSID10181652 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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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Infobox references
Chemical compound

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]

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

  1. ^ Montgomery, Craig T.; Cassels, Bruce K.; Shamma, Maurice (1983-07-01). "The Rhoeadine Alkaloids". Journal of Natural Products. 46 (4): 441–453. doi:10.1021/np50028a001. ISSN 0163-3864. Retrieved 2021-04-07.
  2. ^ Shams, J.; Sahraei, H.; Faghih-Monzavi, Z.; Salimi, SH; Fatemi, SM; Pourmatabbed, A.; Ghoshooni, H.; Kamalinejad, M. (2008). "Effects of Papaver rhoeas Extract on the Tolerance Development to Analgesic Effects of Morphine in Mice". Iranian Journal of Pharmaceutical Research. 7 (2). doi:10.22037/ijpr.2010.757.
  3. ^ Günaydın, Yahya Kemal; Dündar, Zerrin Defne; Çekmen, Bora; Akıllı, Nazire Belgin; Köylü, Ramazan; Cander, Başar (2015-05-13). "Intoxication due to Papaver rhoeas (Corn Poppy): Five Case Reports". Case Reports in Medicine. 2015: –321360. doi:10.1155/2015/321360. ISSN 1687-9627. PMC 4444563. PMID 26074968.