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467-13-0Relevant articles and documents
Combined biological and chemical catalysis in the preparation of oxycodone
Walker, Adam J.,Bruce, Neil C.
, p. 561 - 568 (2004)
The opioid oxycodone was produced from codeine, using a combination of chemical and biological catalysis. The use of novel functionalized ionic liquids permitted this reaction to be performed in a single solvent.
Total Synthesis of (?)-Morphine
Umihara, Hirotatsu,Yokoshima, Satoshi,Inoue, Masayuki,Fukuyama, Tohru
, p. 6993 - 6995 (2017)
Asymmetric total synthesis of (?)-morphine has been accomplished in 18 steps from commercially available 7-methoxy-2-tetralone. Our synthesis features a simple transformation from a readily prepared chiral intermediate, construction of the E-ring by acid-mediated cyclization, and singlet oxygen-mediated manipulation of the C-ring. Transformation of the final stage involves construction of the morphinan skeleton by means of 1,6-addition of in situ generated secondary amine.
Glucosides of morphine derivatives: Synthesis and characterization
Váradi, András,Lévai, Dóra,Tóth, Gerg?,Horváth, Péter,Noszál, Béla,Hosztafi, Sándor
, p. 255 - 262 (2013)
Six 3-O- and 6-O-glucosides of morphine and codeine derivatives were synthesized by means of glucosylation with acetobromo-α-d-glucose. O-Glucosylation at C6 was carried out by the Koenigs-Knorr method, whereas the 3-O-glycoside of morphine was synthesized directly upon stirring morphine with acetobromo-α-d-glucose and aqueous sodium hydroxide in acetone. Complete 1H and 13C NMR assignments are presented for each synthesized compound based on one- and two-dimensional homo- and heteronuclear NMR techniques. Circular dichroism, ultraviolet absorbance, and high-resolution mass spectroscopy data ensure identification and structural characterization of the O-glucoside conjugates. The synthesized glucoside conjugates are potential analgesics; the presented spectral and chromatographic data are useful references for various analytical and metabolic studies including samples of biological origin.
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)
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
Compositions and Methods For Making Alkaloid Morphinans
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Paragraph 0051; 0236-0238, (2017/09/30)
Methods that may be used for the manufacture of a class of chemical compounds known as morphinans, including neopine, are provided. Compositions useful for the synthesis of morphinans, including neopine, are also provided.
Thiol-Reactive Analogues of Galanthamine, Codeine, and Morphine as Potential Probes to Interrogate Allosteric Binding within Nicotinic Acetylcholine Receptors
Gallagher, Ryan,Chebib, Mary,Balle, Thomas,McLeod, Malcolm D.
, p. 1834 - 1841 (2015/12/26)
Alkaloids including galanthamine (1) and codeine (2) are reported to be positive allosteric modulators of nicotinic acetylcholine receptors (nAChRs), but the binding sites responsible for this activity are not known with certainty. Analogues of galanthamine (1), codeine (2), and morphine (3) with reactivity towards cysteine thiols were synthesized including conjugated enone derivatives of the three alkaloids 4-6 and two chloro-alkane derivatives of codeine 7 and 8. The stability of the enones was deemed sufficient for use in buffered aqueous solutions, and their reactivity towards thiols was assessed by determining the kinetics of reaction with a cysteine derivative. All three enone derivatives were of sufficient reactivity and stability to be used in covalent trapping, an extension of the substituted cysteine accessibility method, to elucidate the allosteric binding sites of galanthamine and codeine at nAChRs.
On the features of reactivity of 8-[(1E)-2-phenylethenyl]-substituted thebaine and codeinone derivatives
Moiseev,Shishkov,Kalinin
body text, p. 557 - 560 (2011/11/05)
An improved method for the synthesis of 8-[(1E)-2-phenylethenyl]codeinone dimethyl ketal was described. The ability of [(1E)-2-phenylethenyl] substituent to stabilize effectively the π-system of the ring C is responsible for the essential difference in both the reactivity and the compositions of products formed in the reactions of the corresponding substituted and unsubstituted codeinone and thebaine derivatives.
Total synthesis of (-)-morphine
Koizumi, Hifumi,Yokoshima, Satoshi,Fukuyama, Tohru
, 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.
Salutaridine reductase and morphine biosynthesis
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, (2008/06/13)
Plants of the order Ranunculales, especially members of the species Papaver, accumulate a large variety of benzylisoquinoline alkaloids with about 2,500 structures. But only the opium poppy, Papaver somniferum, and Papaver setigerum, are able to produce morphinan alkaloids such as the analgesic morphine or the antitussive codeine. We investigated the molecular basis for this exceptional biosynthetic capability by comparison of alkaloid profiles with gene expression profiles between sixteen different Papaver species and identified one cDNA which exhibits very similar expression pattern to previously isolated cDNAs coding for enzymes in benzylisoquinoline biosynthesis and which showed the highest amino acid identity to reductases in menthol biosynthesis. When expressed, the protein encoded by this cDNA reduced the keto group of salutaridine yielding salutaridinol, an intermediate in morphine biosynthesis. The stereoisomer epi-salutaridinol was not formed. The encoded protein was identified as salutaridine reductase (SalR; EC 1.1.1.248) and it was found to belongs to the family of the short chain dehydrogenases / reductases.
Synthesis and binding studies of 2-arylapomorphines
Sondergaard, Kare,Kristensen, Jesper Langgaard,Palner, Mikael,Gillings, Nie,Knudsen, Gitte Moos,Roth, Bryan L.,Begtrup, Mikael
, p. 4077 - 4081 (2007/10/03)
From codeine, four different 2-aryl substituted apomorphines were synthesised in 6 steps each. Oxidation of codeine with IBX followed by acid catalysed rearrangement gave morphothebaine, which was selectively triflylated at the 2-position and subsequently O-acetylated at the 11-position. The resulting triflate was coupled in a Suzuki-Miyaura type reaction with a series of 4-substituted arylboronic esters which, after deprotection, gave the desired 2-aryl apomorphines. The analogues were tested for affinity towards a range of dopaminergic, serotonergic and adrenergic receptors. 2-(4-Hydroxyphenyl)- apomorphine exhibited high affinity for the dopamine D2 receptor. A putative ligand-receptor interaction was put forward. The Royal Society of Chemistry 2005.