Article · Wikipedia archive · Last revised Jun 20, 2026

Pseudomorphine

Pseudomorphine 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.

Last revised
Jun 20, 2026
Read time
≈ 1 min
Length
215 w
Citations
4
Source
Wikipedia ↗
Pseudomorphine
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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'-bimorphine1
ChemSpider
ECHA InfoCard 100.169.464
UNII
  • 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
  • CN1CCC23C4C1CC5=C2C(=C(C(=C5)C6=CC7=C8C(=C6O)OC9C81CCN(C(C7)C1C=CC9O)C)O)OC3C(C=C4)O
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).

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

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

See also

References

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. doi:10.1016/S0021-9258(18)84438-6.
  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.