Pseudomorphine

"Dehydromorphine" redirects here. Not to be confused with dihydromorphine.
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 Edit this at Wikidata
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]

  1. ^ a b 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.