467-08-3Relevant academic research and scientific papers
A total synthesis of (±)-codeine by 1,3-dipolar cycloaddition
Erhard, Thomas,Ehrlich, Gunnar,Metz, Peter
, p. 3892 - 3894 (2011/06/24)
Nitrone cycloaddition on a dearomatized bicyclic phenol enabled the facile construction of the correctly configured phenanthrene skeleton of codeine. Further steps yielded allopseudocodeine in a completely diastereoselective manner and finally (±)-codeine by allylic transposition through the hydrolysis of chlorocodides.
The Structure of Methyldihydropseudocodeine Methyl Ether
Theuns, Hubert G.,Janssen, Richard H. A. M.,George, Albert V. E.,Biessels, Hubertus W. A.
, p. 1461 - 1477 (2007/10/02)
Methyldihydropseudocodeine methyl ether, the product reported from the Grignard reaction of methyl magnesiumiodide with pseudocodeine methyl ether, was shown to have no resemblance to dibenzazonine alkaloids, as suggested earlier.It still belongs to the morphinan alkaloids.Spectral analysis shows it to be 5,6-didehydro-3,8β-dimethoxy-7β,17-dimethyl-morphinan-4-ol (4).Another product of the reaction mentioned was shown to be epimeric at C-7 with compound (4), and to have structure (5).In the course of this work the ethanamine bridge of these compounds, as well as of thebaine and codeine, were studied. 13C N.m.r. chemical shifts were assigned for the morphinan alkaloids, related to this research.
Synthesis and Pharmacological Evaluation of an 8β-Bis(2-chloroethyl)amino Opiate as a Nonequilibrium Opioid Receptor Probe
Fang, Su-nan,Bell, K. H.,Portoghese, P. S.
, p. 1090 - 1092 (2007/10/02)
8β--6,7-didehydro-3-hydroxy-17-methyl-4,5α-epoxymorphinan (3) was synthesized from codeine, and its configuration at C-8 was determined by NMR.When evaluated in the quinea pig ileum and mouse vas deferens preparations, 3 was found to be a feeble, reversible agonist in both tissues without any irreversible agonist or antagonist activity.The fact that the 8β-bis-(2-hydroxyethyl)amino analogue was devoid of opioid activity suggests that steric hindrance to ligand-receptor association by a bulky 8-substituent may be responsible for this inactivity.
