Pseudomorphine
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Names | |
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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 | |
CAS Number |
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3D model (JSmol) |
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Abbreviations | 2,2'-bimorphine[1] |
ChemSpider |
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ECHA InfoCard | 100.169.464 ![]() |
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | 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 |
Chemical compound
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
- Thebaine (paramorphine)
- Morphine-N-oxide
- Morphine-3-glucuronide
- Morphine-6-glucuronide
References
- ^ 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.
- ^ A. K. Balls (1927). "Concerning Pseudomorphine". Journal of Biological Chemistry. 71 (2): 537–542. doi:10.1016/S0021-9258(18)84438-6.
- ^ 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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Opium components
- 16-Hydroxythebaine
- Berberine
- Canadine
- Codamine
- Coptisine
- Coreximine
- Cycloartenone
- Cyclolaudenol
- Dehydroreticuline
- Dihydrosanguinarine
- Glaucine
- Isoboldine
- Isocorypalmine
- Laudanidine
- Magnoflorine
- Narceine
- Narceinone
- Norlaudanosoline
- Norsanguinarine
- Oripavine
- Oxysanguinarine
- Palaudine
- Papaverrubine B (O-methyl-porphyroxine)
- Papaverrubine C (epiporphyroxine)
- Reticuline
- Salutaridine (sinoacutine)
- Sanguinarine
- Scoulerine
- Somniferine
- Stepholidine
(Phenanthrenes. Includes opioids)
- Codeine
- Morphine
- Narcotoline
- Neopine
- Perparin
- Papaverrubine D (porphyroxine)
- Pseudocodeine
- Pseudomorphine
- Thebaine
- Cotarnine
- Eupaverine
- Hydrocotarnine
- Laudanosine
- Laudanine
- Noscapine (narcotine)
- Papaverine
- Papaveraldine
- Xanthaline
- α-Allocryptopine
- Corycavamine
- Corycavine
- Cryptopine
- Protopine
- Corydaline
- Corybulbine
- Isocorybulbine
- Capaurine
- Dicentrine
- Glaucine
- Corytuberine
- Cularine
- Corydine
- Isocorydine
- Bulbocapnine
- Adulmine
- Bicuculline
- Bicucine
- Corlumine
- Chelidonine
- β-Homochelidonoine
- Chelerythrine
- Sanguinarine
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