Rhoeadine

Rhoeadine
Names
	Preferred 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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8836;
ChemSpider	171184 ;
KEGG	C09619 ;
PubChem CID	197775;
UNII	9Q9C65WH3B ;
CompTox Dashboard (EPA)	DTXSID10181652 ;
	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 Key: XRBIHOLQAKITPP-SBHAEUEKSA-N ; 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;
	SMILES 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). verify (what is ?) Infobox references

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.[3]

References

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.
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.
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.

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[Montgomery1983-1] 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.

[Günaydın-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.