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 ;
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. These symptoms may be an outlier due to the exceptionally high dose ingested.^[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.

[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.

[1]

[2]

[3]

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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8836
ChemSpider	171184^Y
KEGG	C09619^N
PubChem CID	197775
UNII	9Q9C65WH3B^Y
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^Y Key: XRBIHOLQAKITPP-SBHAEUEKSA-N^Y 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). N verify (what is ^YN ?) Infobox references