Pseudomorphine

Pseudomorphine
IUPAC name (5α,6α)-2-[(5α,6α)-3,6-dihydroxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-2-yl]-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol
Identifiers
Abbreviations	2,2'-bimorphine[1]
CAS number	125-24-6 Y
PubChem	234570
ChemSpider	4590027 Y
UNII	AEZ78QX2G7
Jmol-3D images	Image 1
SMILES CN1CCC23C4C1CC5=C2C(=C(C(=C5)C6=CC7=C8C(=C6O)OC9C81CCN(C(C7)C1C=CC9O)C)O)OC3C(C=C4)O
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,7-10,13-14H2,1-2H3 Key: FOJYFDFNGPRXDR-UHFFFAOYSA-N
Properties
Molecular formula	C34H36N2O6
Molar mass	568.66 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.^[2]

This compound may be synthesized by the oxidative coupling of morphine by potassium ferricyanide.^[1]

See also

• Thebaine (paramorphine)
• Morphine-N-oxide
• Morphine-3-glucuronide
• Morphine-6-glucuronide

References

1. ↑ 1.0 1.1 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. 
2. ↑ A. K. Balls (1927). "Concerning Pseudomorphine". Journal of Biological Chemistry 71 (2): 537–542.