Pseudomorphine - Misplaced Pages

"Dehydromorphine" redirects here. Not to be confused with dihydromorphine.

Pseudomorphine
Names

IUPAC name (5α,6α)-2--17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol
Identifiers
CAS Number	125-24-6
3D model (JSmol)	Interactive image
Abbreviations	2,2'-bimorphine
ChemSpider	4590027
ECHA InfoCard	100.169.464
PubChem CID	234570
UNII	AEZ78QX2G7
CompTox Dashboard (EPA)	DTXSID50924984
InChI InChI=1S/C34H36N2O6/c1-35-9-7-33-19-3-5-23(37)31(33)41-29-25(33)15(13-21(19)35)11-17(27(29)39)18-12-16-14-22-20-4-6-24(38)32-34(20,8-10-36(22)2)26(16)30(42-32)28(18)40/h3-6,11-12,19-24,31-32,37-40H,7-10,13-14H2,1-2H3Key: FOJYFDFNGPRXDR-UHFFFAOYSA-N
SMILES CN1CCC23C4C1CC5=C2C(=C(C(=C5)C6=CC7=C8C(=C6O)OC9C81CCN(C(C7)C1C=CC9O)C)O)OC3C(C=C4)O
Properties
Chemical formula	C₃₄H₃₆N₂O₆
Molar mass	568.670 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Pseudomorphine (also known as oxydimorphine or dehydromorphine) is an inactive, natural dimerisation product of the morphine molecule in tandem and thus a common impurity in morphine concentrations. It was first described by Pelletier in 1835.

This compound may be synthesized by the oxidative coupling of morphine by potassium ferricyanide.

Pseudomorphine contributes very little to morphine's effects. It produces no effects in the central nervous or gastrointestinal systems, but it might have some effects on the circulatory system.

References

^ Bentley, K. W.; Dyke, S. F. (1959). "512. The structure of pseudomorphine". Journal of the Chemical Society (Resumed). 1959: 2574–2577. doi:10.1039/JR9590002574.
A. K. Balls (1927). "Concerning Pseudomorphine". Journal of Biological Chemistry. 71 (2): 537–542. doi:10.1016/S0021-9258(18)84438-6.
Schmidt, Carl F.; Livingston, A. E. (1933-04-01). "A Note Concerning the Actions of Pseudomorphine". Journal of Pharmacology and Experimental Therapeutics. 47 (4): 473–485. ISSN 0022-3565.

v t e Opium components
Alkaloids	16-Hydroxythebaine Berberine Canadine Codamine Coptisine Coreximine Cycloartenone Cyclolaudenol Dehydroreticuline Dihydrosanguinarine Glaucine Isoboldine Isocorypalmine Laudanidine Magnoflorine Narceine Narceinone Norlaudanosoline Norsanguinarine Oripavine Oxysanguinarine Palaudine Papaverrubine B (O-methyl-porphyroxine) Papaverrubine C (epiporphyroxine) Reticuline Salutaridine (sinoacutine) Sanguinarine Scoulerine Somniferine Stepholidine
Morphine group (Phenanthrenes. Includes opioids)	Codeine Morphine Narcotoline Neopine Perparin Papaverrubine D (porphyroxine) Pseudocodeine Pseudomorphine Thebaine
Isoquinolines	Cotarnine Eupaverine Hydrocotarnine Laudanosine Laudanine Noscapine (narcotine) Papaverine Papaveraldine Xanthaline
Protopine group	α-Allocryptopine Corycavamine Corycavine Cryptopine Protopine
Tetrahydroprotoberberine group	Corydaline Corybulbine Isocorybulbine Capaurine
Aporphine group	Dicentrine Glaucine Corytuberine Cularine Corydine Isocorydine Bulbocapnine
Phtalide-isoquinolines	Adulmine Bicuculline Bicucine Corlumine
α-Naphthaphenanthridines	Chelidonine β-Homochelidonoine Chelerythrine Sanguinarine
Other components	Meconic acid Cycloartenol

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References