Pseudomorphine

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]

Pseudomorphine
Names
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
3D model (JSmol)
Abbreviations 2,2'-bimorphine[1]
ChemSpider
ECHA InfoCard 100.169.464
UNII
Properties
C34H36N2O6
Molar mass 568.670 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

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.[3]

See also

References

  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.
  3. 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.


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