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Topic: Codeinone

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Jim Valvano

	Synthesis of Oxycodone from Codeine
		A solution of codeinone dienol acetate (0.50 g, 1.48 mmol), formic acid (0.7 ml), hydrogen peroxide (0.43 g, 30%, 3.79 mmol), and water (1.4 ml) was heated at 43-44°C for 6 hr and cooled to rt.
		Codeinone (6.0 g) with toluene (104 g) was added to a reaction flask equipped with a mechanical stirrer, thermocouple, Dean-Stark trap with condenser attached, and a nitrogen-inlet adapter.
		Codeinone was prepared by oxidation of codeine phosphate or codeine.
	designer-drugs.com /pte/12.162.180.114/dcd/chemistry/oxycodone.html (2978 words)

	UNODC - Bulletin on Narcotics - 1950 Issue 2 - 003
		Codeine itself is oxidized into codeinone, and the methyl ether of the enol form of this is the same as thebaine.
		Moreover, since the action of acetic anhydride on codeinone makes it possible to isolate 3-methoxy-4:6 dihydroxyphenanthrene,[16] the respective positions of the phenol group and of the alcoholic hydroxyl must clearly be 3 and 6.
		The constitution of these phenanthrene derivatives (morphol,[17] morphenol, thebaol,[18] etc.) was explained by Pschorr, who pioneered in the field of phenanthrene synthesis and succeeded in synthesizing the substitute phenanthrenes which have made it possible to identify by direct comparison most of the products of degradation of the morphine alkaloids.
	www.unodc.org /unodc/en/bulletin/bulletin_1950-01-01_2_page004.html (5222 words)

	Patent 4054566: Process for converting neopinone to codeinone
		Since codeinone can be easily converted to codeine by reducing the ketone group of codeinone to a hydroxyl group, a procedure for converting neopinone to codeinone would be an advancement in the art.
		When a mixture containing neopinone and codeinone is employed it is generally a mixture containing any portion of codeinone from about 1% to about 99% by weight and from about 99% to about 1% neopinone by weight based on the total weight of the mixture.
		of codeinone (100% codeinone) as analyzed by nmr and reduction to codeine with sodium borohydride and analysis of the codeine by gc.
	www.freepatentsonline.com /4054566.html (1722 words)

	Method for Producing Oxycodone
		Codeinone was added to a mixture of p-toluenesulfonic acid (dehydrated prior to reaction), absolute methanol and dried benzene, the solution refluxed for 3 hours under azeotropic removal of water, and the reaction mixture purified by washing with diluted sodium hydroxide, to obtain thebaine.
		Codeinone is then reacted with an organosilyl compound having an effective leaving group, such as a halogen.
		A codeinone dienol silyl ether, such as the intermediate compound formed in the conversion of codeine to oxycodone according to certain embodiments of the present invention, is disclosed in pending European patent application No. EP 0 889 045 A1 to Jen-Sen Dung.
	www.poppies.org /news/99502129975371.shtml (6398 words)

	Patent 4052402: Process for synthesizing codeinone from thebaine
		Codeinone is prepared by reacting thebaine with a hydrogen halide, under anhydrous conditions, in the presence of iodine as a catalyst, at a temperature of less than 10.degree.
		The conversion of thebaine to codeinone via 14-bromocodeinone and neopinone was also attempted by Conroy and Krausz, J. Am.
		The codeinone which precipitates during concentration of the organic solution, which exhibits a clear pink color, is then filtered and washed with diethyl ether.
	www.freepatentsonline.com /4052402.html (582 words)

	Synthesis of Oxycodone from Codeine - [www.rhodium.ws]
		A mixture of codeinone (5.98 g, 0.02 mole), sodium acetate (1.77 g, 0.02 mole) and acetic anhydride (35.76 g, 0.35 mole) in toluene (6 ml) was heated at 90°C about 105°C for 5 hr, cooled, diluted with CH Cl
		A solution of codeinone dienol acetate (1.12 g, 3.3 mmol), formic acid (90% aqueous solution, 0.80 g, 15.6 mmol), hydrogen peroxide (31% aqueous solution, 0.90 g, 8.2 mmol), and water (1.60 g) was allowed to stir at 40-42°C for 4.5 hr, cooled to room temperature, basified with concentrated NH
		A solution of codeinone dienol acetate (1.16 g, 3.4 mmol), oxalic acid (0.70 g, 7.4 mmol) and 3-chloroperoxybenzoic acid (57.about.86%, 0.83 g) in glacial acetic acid (10.02 g) was allowed to stir at room temperature for 6 hr, basified with concentrated NH OH, and extracted with CH Cl
	www.erowid.org /archive/rhodium/chemistry/oxycodone.html (3036 words)

	Production of thebaine and oripavine - US Patent 6723894 (Site not responding. Last check: 2007-11-07)
		Codeinone and morphinone vary only in the presence of a methyl group at the 3-position of codeinone.
		The enzyme codeinone reductase (NADPH) is believed to be active in both pathways, reducing codeinone to codeine and morphinone to morphine.
		Codeinone reductase has been isolated, its activity is described and its physical properties are characterized by Lenz, R., and Zenk, M. H., Eur.
	www.patentstorm.us /patents/6723894.html (5631 words)

	Oxycodone from Codeine
		1074); (2) the oxidation of codeinone pyrrolidinyl di-enamine to 1 4-hydroxycodeinone (30-40% yield, I. Seki, Chem.
		Alternatively, codeinone dienol acetate is reacted with a peroxyacid oxidizing agent in an aqueous or non-aqueous system with a weak acid at room temperature to form 14-hydroxycodeinone in excellent yield.
		A mixture of codeinone (5.98 g, 0.02 mole), sodium acetate (1.77 g, 0.02 mole) and acetic anhydride (35.76 g, 0.35 mole) in toluene (6 ml) was heated at 90-105.degree.
	www.poppies.org /news/99502122134978.shtml (7088 words)

	Cell death-inducing activity of opiates in human oral tumor cell lines.
		A study of structurally-related compounds suggested that the alpha,beta-unsaturated ketone group of codeinone was responsible for its antitumor cytotoxicity.
		The cytotoxic activity of codeinone was significantly reduced by N-acetylcysteine, but not affected by FeCl3, CuCl2, CoCl2, sodium ascorbate or catalase.
		These data suggest that codeinone induces cytotoxicity in oral tumor cell lines, possibly by a Michael-like addition of a protein SH or of an amino group to the bouble bond of codeinone.
	www.pdg.cnb.uam.es /UniPub/iHOP/gp/9462498.html (207 words)

	The Scientist :: RNAi turns poppies off morphine, Nov. 15, 2004
		The enzymology of the entire morphine pathway is largely elucidated, but virtually nothing is known of what regulates the accumulation of morphine and its intermediates in poppies.
		Larkin and colleagues employed RNA interference to silence codeinone reductase (COR), the penultimate enzyme in morphine biosynthesis, and shed light on pathway controls.
		Larkin and colleagues suggest the unexpected reticuline phenotype may have been caused by a buildup of morphine substrates codeinone and neopinione that triggered negative feedback on one or more earlier enzymes or transport steps of the morphine branch.
	www.biomedcentral.com /news/20041115/01 (712 words)

	Codeinone from Thebaine (Site not responding. Last check: 2007-11-07)
		The extract was added to the previous organic phase, washed with water, and dried with anhydrous sodium sulphate.
		The solvent was then removed from the solution under vacuum until its volume was reduced to 1/leo Codeinone of a clear pure colour was obtained by concentration of the solution, filtration and washing with ethyl ether.
		96 g Codeinone having a melting point of 165-167°C and a purity of 90.36% were obtained with a calculated yield of 98%.
	designer-drugs.com /pte/12.162.180.114/dcd/chemistry/codeinone.html (277 words)

	In vivo formation of codeinone and morphinone from codeine. Isolation and identification from guinea pig bile -- Ishida ...
		In vivo formation of codeinone and morphinone from codeine.
		Articles by Ishida, T. Articles by Toki, S. In vivo formation of codeinone and morphinone from codeine.
		Codeinone (CO) and morphinone (MO) were isolated and identified in the bile
	dmd.aspetjournals.org /cgi/content/abstract/19/5/895 (217 words)

	Crystal Structure of Bacterial Morphinone Reductase and Properties of the C191A Mutant Enzyme -- Barna et al. 277 (34): ...
		Protein Purification and Mutagenesis-- MR was purified from a recombinant strain of E.
		donor in the reduction of 2-cyclohexenone and codeinone.
		Transients obtained for the oxidation of wild-type and C191A MR by codeinone.
	www.jbc.org /cgi/content/full/277/34/30976 (5012 words)

	UNODC - Bulletin on Narcotics - 1958 Issue 3 - 006
		Codeine can be oxidized to codeinone with potassium permanganate, and codeinone reacts with the diazo reagent to form a coloured compound.
		Thebaine, as an enol ether of codeinone, can be transformed into the latter by acid hydrolysis, and undergoes the same colour reaction.
		With this degree of acidity, the codeinone already present at the beginning of oxidization is oxidized fast enough and the extinctions, even for minute quantities of codeine (0.04-0.2 mg) are still large enough to permit of sufficiently accurate measurement, as shown by table 7.
	www.unodc.org /bulletin/bulletin_1958-01-01_3_page007.html (8741 words)

	ANESTH.OR.JP INFORMATION (Site not responding. Last check: 2007-11-07)
		"We have recently found that codeinone, an oxidation metabolite of codeine, induced apoptosis characterized by internucleosomal DNA fragmentation and mitochondrial cytochrome c release in HL-60 human promyelocytic leukemic cell lines, most effectively among 10 opioids.
		Fluorometric assay showed that codeinone time-dependently activatied caspase 3 and 9, but not caspase 8, suggesting the activation of intrinsic apoptotic signaling pathway via mitochondria.
		Codeinone did not significantly change the MnSOD activity nor its mRNA expression.
	kansai.anesth.or.jp /kako/masui50/abstract/E1-03.html (190 words)

	codeinone (Site not responding. Last check: 2007-11-07)
		Catalyses the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum.
		reticuline to thebaine biosynthesis EC 1.1.1.218 morphine 6-dehydrogenase EC 1.1.1.247 codeinone reductase (NADPH)
		are salutaridinol 7- O -acetyltransferase and codeinone reductase the penultimate enzyme of the morphine pathway that reduces codeinone to codeine.
	codeinone.networklive.org (325 words)

	Codeinone - Wikipedia, the free encyclopedia
		Codeinone can described as the methylether of morphinone: 3-Methyl-morphinone.
		Codeinone can be also described as the Ketone of Codeine: Codein-6-on
		This page was last modified 02:31, 26 July 2005.
	en.wikipedia.org /wiki/Codeinone (88 words)

	Codeine And Morphine: Advantages Of Morphine Pump on Popular Links (Site not responding. Last check: 2007-11-07)
		morphine addiction Pathways reducing codeinone to codeine and morphinone to morphine.
		Codeinone reductase has.Most common are morphine sulfate and ethex morphine image morphine hydrochloride.
		Effects similar to morphine except euphoria is similar to codeine nausea and vomiting is.1 Pupil diameter gradually returned to baseline values over the course of the remainder of the study
	codeine-and-morphine.popularlinks.info (463 words)

	Annotated Rhodium Chemistry Archive - Opioid chemistry - Heroin Helper (Site not responding. Last check: 2007-11-07)
		Codeinone, along with codeine, is the chemical most used to create morphine in the laboratory (except that as a society, we get a lot more morphine directly from poppies than we use).
		Should someone have thebaine just sitting around, this procedure could probably be carried out by anyone.
		There is a lot of information on making intermediaries such as the process for changing codeinone to 14-hydroxycodeinone with hydrogen peroxide (H2O2).
	www.heroinhelper.com /curious/chemistry/rhodium.shtml (1880 words)

	[No title]
		To establish the synthetic route to the desired precursors suitable for labelling, the apomorphine backbone was chosen as the model compound.
		The synthesis started by an oxidation of codeine (1) to codeinone (2) which underwent ring-opening followed by sceletal rearrangement to give morphothebaine (3) when treated with methanesulfonic acid (Scheme 1).
		After the sceletal rearrangement the nitrogen will be protected with an appropriate protecting group which can easily be removed at a late stage of the synthetic sequence.
	info.dfh.dk /phd/forskningensdag/2004/p25.doc (620 words)

	EC 1.1.1.247 (Site not responding. Last check: 2007-11-07)
		Comments: Catalyses the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum.
		Lenz, R. and Zenk, M.H. Stereoselective reduction of codeinone, the penultimate step during morphine biosynthesis in Papaver somniferum.
		Lenz, R. and Zenk, M.H. Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures.
	www.chem.qmw.ac.uk /iubmb/enzyme/EC1/1/1/247.html (70 words)

	Fermentation Biotechnology
		Using alginate as the immobilising polymer, digitoxin from Digitalis lanata was converted into digoxin, which is a therapeutic agent in great demand.
		Similarly, codeinone was converted into codeine and tyrosine from Mucuna pruriens was converted into DOPA.
		It is possible to induce production or enhance production of a compound in cultures by using elicitors, which may be micro-organisms.
	www.fbae.org /Channels/General_issues/fermentation_biotechnology.htm (3156 words)

	The opium poppy : sites of alkaloid biosynthesis (Site not responding. Last check: 2007-11-07)
		The benzylisoquinoline alkaloids of opium poppy accumulate in the cytoplasm, or latex, of specialized laticifers that accompany vascular tissues throughout the plant.
		However, immunofluorescence labeling using affinity-purified antibodies showed that three key enzymes, (S)-N-methylcoclaurine 3'-hydroxylase (CYP80B1), berberine bridge enzyme (BBE), and codeinone reductase (COR), involved in the biosynthesis of morphine and the related antimicrobial alkaloid sanguinarine, are restricted to the parietal region of sieve elements adjacent or proximal to laticifers.
		The localization of laticifers was demonstrated using antibodies specific to the major latex protein (MLP), which is characteristic of the cell type.
	www.opioids.com /opium/alkaloids.html (206 words)

	Tramadol, buy tramadol, antibiotics, Weight Loss drugs, weight loss herbs, weight loss herbal formula, weight loss, ... (Site not responding. Last check: 2007-11-07)
		RX 336-M, a new chemical tool in the analysis of the quasi-morphine withdrawal syndrome.
		Cowan A. RX 336-M (7,8-dihydro-5',6'-dimethylcyclohex-5'-eno-1',2',8',14 codeinone) and four other chemically-diverse agents--AG-3-5 (1-[2-hydroxyphenyl]-4-[3-nitrophenyl]-1,2,3,6-tetrahydropyrimidine-2-one), Sgd 8473 (alpha-[4-chlorobenzylideneamino)-oxy]-isobutyric acid), thyrotropin releasing hormone (TRH), and sodium valproate--each induce signs of withdrawal, most notably 'wet-dog' shaking, after acute i.p.
		They are therefore additions to a recently recognized and, as yet, ill-defined class of behaviorally active compounds.
	www.wellstreetpharmacy.com /ref-depakote/depakote-research-abs3.764.html (596 words)

	Plant Tissue Culture: an alternative for production of useful metabolite. Chapter 7.
		The efficient production of thebaine and codeine using cell culture systems by de novo synthesis was not successful, Furuya et al.
		(153), therefore studied the biotransformation of codeinone to codeine using immobilized cells of P.
		The conversion yield was 70.4% and about 88% of codeine converted was excreted into the medium.
	www.fao.org /docrep/t0831e/t0831e08.htm (4969 words)

	Erowid Psychoactive Vaults
		About hydrocodone: Prepn by hydrogenation of codeinone: Mannich, Lowenheim, _Arch Pharm_ 258, 295 (1920); by oxidation of dihydrocodeine, Ger.
		I wonder if all those methods for reduction of the double bond in hydroxycodeine to get oxycodone are applicable to reduction of codeine or codeinone.
		The one about "reduction of the bromination products" sounds like they add bromine across the double bond and then reduce the halide, I believe hydrides (LAH, NaBH4) can be used for this, and maybe H2 + catalyst, but I'm really not too sure.
	www.erowid.org /chemicals/opiates/opiates_info2.shtml (4593 words)

	Tramadol, buy tramadol, antibiotics, Weight Loss drugs, weight loss herbs, weight loss herbal formula, weight loss, ... (Site not responding. Last check: 2007-11-07)
		Lysergic acid diethylamide antagonizes shaking induced in rats by five chemically different compounds.
		Cowan A, Watson T. Thyrotropin-releasing hormone (TRH), sodium valproate, AF-3-5 (1-[2-hydroxyphenyl]-4-[3-nitrophenyl]-1,2,3,6-tetrahydropyrimidine-2-one), RX336-M (7,8-dihydro-5',6'-dimethylcyclohex-5'-eno-1',2',8',14 codeinone), and Sgd 8473 (alpha-[4-chlorobenzylideneamino)-oxy]-isobutyric acid) each induced repetitive shaking of the body of rats after intraperitoneal injection.
		This action of the five diverse chemicals appears to be subserved by a common pharmacological component, because pretreatment with d-lysergic acid diethylamide (0.03--1.0 mg kg-1, s.c.) attenuated the shaking behavior in a dose-related manner, and cross tolerance was found between RX336-M and TRH, sodium valproate, and AG-3-5.
	www.wellstreetpharmacy.com /ref-depakote/depakote-research-abs3.45.html (651 words)

	Molecular Characterization of the Salutaridinol 7-O-Acetyltransferase Involved in Morphine Biosynthesis in Opium Poppy ...
		The number of restriction endonuclease recognition sites that occur within the open reading frame are as follows: EcoRI, 0; HindIII, 0; ApoI, 1; SalI, 1; SpeI, 1; HincII, I; and MspI, 3.
		This is in stark contrast to the other known morphine-specific biosynthetic gene cor1 encoding codeinone reductase for which
		of the morphine pathway that reduces codeinone to codeine (13).
	www.jbc.org /cgi/content/full/276/33/30717 (4042 words)

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