Pseudomorphine

{{Redirect-distinguish|Dehydromorphine|dihydromorphine}} {{Chembox | ImageFile = Pseudomorphine skeletal.svg | ImageClass = skin-invert-image | ImageFile_Ref = {{chemboximage|correct|??}} | ImageName = | IUPACName = (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 |Section1={{Chembox Identifiers | Abbreviations = 2,2'-bimorphine<ref name=bentley/> | CASNo = 125-24-6 | CASNo_Ref = {{cascite|correct|??}} | UNII = AEZ78QX2G7 | PubChem = 234570 | ChemSpiderID = 4590027 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | EINECS = | KEGG = | KEGG_Ref = {{keggcite|correct|kegg}} | SMILES = CN1CCC23C4C1CC5=C2C(=C(C(=C5)C6=CC7=C8C(=C6O)OC9C81CCN(C(C7)C1C=CC9O)C)O)OC3C(C=C4)O | StdInChI = 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 | StdInChIKey = FOJYFDFNGPRXDR-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=34 | H=36 | N=2 | O=6 }} }}

'''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.<ref>{{cite journal | author = A. K. Balls | title = Concerning Pseudomorphine | journal = Journal of Biological Chemistry | year = 1927 | volume = 71 | issue = 2 | pages = 537–542 | doi = 10.1016/S0021-9258(18)84438-6 | url = http://www.jbc.org/content/71/2/537 | doi-access = free }}</ref>

This compound may be synthesized by the oxidative coupling of morphine by potassium ferricyanide.<ref name=bentley>{{cite journal | title = 512. The structure of pseudomorphine | year = 1959 | last1 = Bentley | first1 = K. W. | last2 = Dyke | first2 = S. F. | journal = Journal of the Chemical Society (Resumed) | volume = 1959 | pages = 2574–2577 | doi = 10.1039/JR9590002574 }}</ref>

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.<ref>{{Cite journal|last1=Schmidt|first1=Carl F.|last2=Livingston|first2=A. E.|date=1933-04-01|title=A Note Concerning the Actions of Pseudomorphine|url=http://jpet.aspetjournals.org/content/47/4/473|journal=Journal of Pharmacology and Experimental Therapeutics|language=en|volume=47|issue=4|pages=473–485|issn=0022-3565}}</ref>

==See also== *Thebaine (paramorphine) *Morphine-N-oxide *Morphine-3-glucuronide *Morphine-6-glucuronide

==References== {{Reflist|2}}

Category:4,5-Epoxymorphinans