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76-57-3Relevant articles and documents
Enantioselective synthesis of (-)-codeine and (-)-morphine
Trost, Barry M.,Tang, Weiping
, p. 14542 - 14543 (2002)
A new synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges employing a Pd-catalyzed asymmetric allylic alkylation to set the stereochemistry. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate, the latter available from glutaraldehyde and the Emmons-Wadsworth-Horner phosphate reagent. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine is formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine. Copyright
BIOTRANSFORMATION OF CODEINONE TO CODEINE BY IMMOBILIZED CELLS OF PAPAVER SOMNIFERUM
Furuya, Tsutomu,Yoshikawa, Takafumi,Taira, Megumi
, p. 999 - 1002 (1984)
Papaver somniferum (opium poppy) cells were immobilized in calcium alginate, where they continued to live with their biological activity for 6 months.The immobilized living cells performed the biotransformation of (-)-codeinone to (-)-codeine in both a shake flask and a column bioreactor.The biotransformation ratio in the shake flask (70.4percent) was higher than that in the cell suspension (60.8percent).Furthermore, 88percent of the codeine converted was extracted in the medium.The column bioreactor was functional for 30 days under optimal conditions (20 deg C, 3,75 vvm in aeration), whereas the ratio was 41.7percent.Key Word Index - Papaver somniferum; Papaveraceae; immobilized cell; biotransformation; bioreactor; codeinone; codeine; GC/MS; SIM.
Total Synthesis of Codeine
Li, Qilin,Zhang, Hongbin
, p. 16379 - 16382 (2015/11/09)
In this paper, a new strategy towards the synthesis of codeine and morphine is reported. This new approach features a cascade cyclization to construct the dihydrofuran ring, and an intramolecular palladium catalyzed C-H olefination of unactivated aliphatic alkene to install the morphinan ring system.
On the selection of an opioid for local skin analgesia: Structure-skin permeability relationships
Musazzi, Umberto M.,Matera, Carlo,Dallanoce, Clelia,Vacondio, Federica,De Amici, Marco,Vistoli, Giulio,Cilurzo, Francesco,Minghetti, Paola
, p. 177 - 185 (2015/05/20)
Recent studies demonstrated that post-herpetical and inflammatory pain can be locally managed by morphine gels, empirically chosen. Aiming to rationalize the selection of the most suitable opioid for the cutaneous delivery, we studied the in vitro penetration through human epidermis of eight opioids, evidencing the critical modifications of the morphinan core. Log P, log D, solid-state features and solubility were determined. Docking simulations were performed using supramolecular assembly made of ceramide VI. The modifications on position 3 of the morphinan core resulted the most relevant in determining both physicochemical characteristics and diffusion pattern. The 3-methoxy group weakened the cohesiveness of the crystal lattice structure and increased the permeation flux (J). Computational studies emphasized that, while permeation is essentially controlled by molecule apolarity, skin retention depends on a fine balance of polar and apolar molecular features. Moreover, ChemPLP scoring the interactions between the opioids and ceramide, correlated with both the amount retained into the epidermis (Qret) and J. The balance of the skin penetration properties and the affinity potency for μ-receptors evidenced hydromorphone as the most suitable compound for the induction of local analgesia.
Transformation of codeine and codeine-6-glucuronide to opioid analogues by urine adulteration with pyridinium chlorochromate: Potential issue for urine drug testing
Luong, Susan,Ung, Alison T.,Kalman, John,Fu, Shanlin
, p. 1609 - 1620 (2014/06/23)
Rationale: Pyridinium chlorochromate (PCC) is the active ingredient of 'Urine Luck', a commercially available in vitro adulterating agent used to conceal the presence of drugs in a urine specimen. The exposure of codeine and its major glucuronide metabolite codeine-6-glucuronide (C6G) to PCC was investigated to determine whether PCC is an effective masking agent for these opiate compounds. Methods: Following the addition of PCC to both spiked and authentic codeine and C6G-positive urine specimens, the samples were monitored using liquid chromatography/mass spectrometry (LC/MS). Stable reaction products were identified and characterized using high-resolution MS analysis and, where possible, nuclear magnetic resonance (NMR) analysis. Results: It was determined that PCC effectively oxidizes codeine and C6G, thus altering the original codeine-to-C6G ratio in the urine specimen. Four reaction products were identified for codeine: codeinone, 14-hydroxycodeinone, 6-O-methylcodeine and 8-hydroxy-7,8-dihydrocodeinone. Similarly, three reaction products were identified for C6G: codeinone, codeine and a lactone of C6G (tentative assignment). Conclusions: Besides addressing the complications added to interpretation, more investigation is warranted to further determine their potential for use as markers for monitoring the presence of codeine and C6G in urine specimens adulterated with PCC. Copyright
Polonovski-type N-demethylation of N-methyl alkaloids using substituted ferrocene redox catalysts
Kok, Gaik B.,Scammells, Peter J.
experimental part, p. 2587 - 2594 (2012/09/22)
Various substituted ferrocenes have been trialed as catalysts in the nonclassical Polonovski reaction for N-demethylation of N-methyl alkaloids. Earlier studies suggest that conditions facilitating a higher ferrocenium ion concentration lead to superior outcomes. In this regard, the bifunctional ferrocene FcCH2CO2H, with electron donor and acceptor moieties in the same molecule, has been shown to be advantageous for use as a catalyst in the N-demethylation of a number of tertiary N-methylamines such as codeine, thebaine, and oripavine. These substrates are readily N-demethylated under mild conditions, employing sub-stoichiometric amounts of the substituted ferrocene at ambient temperature. These reactions are equally efficient in air and may also be carried out in one pot. Georg Thieme Verlag Stuttgart · New York.
A total synthesis of (±)-codeine by 1,3-dipolar cycloaddition
Erhard, Thomas,Ehrlich, Gunnar,Metz, Peter
supporting information; experimental part, 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.
Total synthesis of (-)-morphine
Koizumi, Hifumi,Yokoshima, Satoshi,Fukuyama, Tohru
supporting information; experimental part, p. 2192 - 2198 (2011/06/19)
We have developed an efficient total synthesis of (-)-morphine in 5% overall yield with the longest linear sequence consisting of 17 steps from 2-cyclohexen-1-one. The cyclohexenol unit was prepared by means of an enzymatic resolution and a Suzuki-Miyaura coupling as key steps. Construction of the morphinan core features an intramolecular aldol reaction and an intramolecular 1,6-addition. Furthermore, mild deprotection conditions to remove the 2,4-dinitrobenzenesulfonyl (DNs) group enabled the facile construction of the morphinan skeleton. We have also established an efficient synthetic route to a cyclohexenol unit containing an N-methyl-DNsamide moiety.
SYNTHESIS OF MORPHINE AND RELATED DERIVATIVES
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Page/Page column 84-85, (2010/12/17)
The present invention relates to methods for the synthesis of galanthamine, morphine, intermediates, salts and derivatives thereof, wherein the starting compound is biphenyl.
Further investigation of the N-demethylation of tertiary amine alkaloids using the non-classical Polonovski reaction
Thavaneswaran, Shanti,Scammells, Peter J.
, p. 2868 - 2871 (2007/10/03)
The iron salt-mediated Polonovski reaction efficiently N-demethylates certain opiate alkaloids. In this process, the use of the hydrochloride salt of the tertiary N-methyl amine oxide was reported to give better yields of the desired N-demethylated product. Herein, we report further investigation into the use of N-oxide salts in the iron salt-mediated Polonovski reaction. An efficient approach for the removal of iron salts that greatly facilitates isolation and purification of the N-nor product is also described.