120-29-6Relevant articles and documents
Kinetics of oxidation of atropine by alkaline KMnO4 in aqueous solutions
Saleh, Abdullah I.,Al-Ghreizat, Sanad K.,Abdel-Halim, Hamzeh M.
, p. 3877 - 3882 (2015)
Kinetics of oxidation of atropine by alkaline KMnO4 has been studied in aqueous solutions at various temperatures. Kinetic I measurements were performed at constant pH and constant ionic strength, under pseudo-first order condition in which the concentration i of atropine was around an order of magnitude greater than that of KMnO4. The observed rate constant was obtained by following the change in absorbance of the reaction mixture with time at a predetermined wavelength. The overall rate constant and the orders of the I reaction with respect to concentrations of both atropine and KMnO4 were determined. Two observed rates and hence, two rates constant | were found. This indicates that the oxidation process occurs in two steps with the formation of intermediates. A suggested mechanism for I the reaction is given which agrees with kinetics results. The activation energy of the process was convoluted from temperature effect on. the rate of the reaction.
Difficulties in Differentiating Natural from Synthetic Alkaloids by Isotope Ratio Monitoring using 13 C Nuclear Magnetic Resonance Spectrometry
Robins, Richard J.,Romek, Katarzyna M.,Grand, Mathilde,Nun, Pierrick,Diomande, Didier,Julien, Maxime,Remaud, Gérald S.
, p. 935 - 940 (2018)
Within the food and pharmaceutical industries, there is an increasing legislative requirement for the accurate labeling of the product's origin. A key feature of this is to indicate whether the product is of natural or synthetic origin. With reference to
The synthesis and separation of [3-2H]tropine and [3-2H]pseudotropine (Ψ-tropine)
Bartholomew,Smith,Darcy,Trudgill,Hopper
, p. 85 - 91 (1994)
Tropine was reduced using sodium borodeuteride to give a mixture of the epimers [3-2H]tropine and [3-2H]pseudotropine with the latter compound predominating and constituting about 70% of the mixture. Crystallisation of the product from diethyl ether gave crystals of pure [3-2H]pseudotropine and a supernatant solution containing a mixture of the epimers. Acetylation of this mixture using acetyl chloride preferentially acetylated the pseudotropine and the acetylated products were separated from the tropine by flash chromatography to leave a sample of pure [3-2H]tropine.
CRYSTALLINE ATROPINE SULFATE
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Page/Page column 4-5, (2014/07/21)
The present invention relates to crystalline polymorph form of Atropine sulfate and process for the preparation thereof.
Spectroscopic investigation and oxidation of the anticholinergic drug atropine sulfate monohydrate by hexacyanoferrate(III) in aqueous alkaline media: A mechanistic approach
Meti, Manjunath,Nandibewoor, Sharanappa,Chimatadar, Shivamurti
, p. 477 - 487 (2014/06/09)
The oxidation of the anticholinergic drug atropine sulfate monohydrate by hexacyanoferrate(III) in aqueous alkaline media was investigated spectrophotometrically by monitoring the decrease in absorbance of hexacyanoferrate(III) (HCF(III)). Oxidation products were identied. The oxidation mechanism was proposed from kinetic studies. The reaction constants involved in the dierent steps of the mechanism were calculated. The eects of added products, ionic strength, and dielectric constant of the reaction were investigated. The polymerization test revealed that oxidation occurred with intervention of free radicals. The activation parameters were evaluated. TUeBITAK.
Spectroscopic investigation and reactivities of ruthenium(iii) catalyzed oxidation of anticholinergic drug atropine sulfate monohydrate by hexacyanoferrate(iii) in aqueous alkaline media: A mechanistic approach
Meti, Manjunath D.,Nandibewoor, Sharanappa T.,Chimatadar, Shivamurti A.
, p. 263 - 272 (2013/11/19)
The kinetics of oxidation of an atropine sulfate monohydrate (ASM) by hexacyanoferrate (HCF) (III) has been investigated spectrophotometrically in presence of ruthenium(III) catalyst in aqueous alkaline medium at 25°C. The stoichiometry is 1: 2. The reaction is first order in HCF(III) and has less than unit order in ASM concentrations. The effect of ionic strength and dielectric constants were studied on the rate of reaction. The active species of oxidant and catalyst are Fe(CN)63- and [Ru(H2O)5(OH)]2+, respectively. A suitable mechanism is proposed. The catalytic constant (KC) was also calculated. The activation parameters and thermodynamic quantities are also determined and discussed.
Catalytic activity of ruthenium(III) on the oxidation of an anticholinergic drug-atropine sulfate monohydrate by copper(III) periodate complex in aqueous alkaline medium - Decarboxylation and free radical mechanism
Byadagi, Kirthi S.,Nandibewoor, Sharanappa T.,Chimatadar, Shivamurti A.
, p. 617 - 627 (2013/09/23)
Atropine sulfate monohydrate (ASM) is an anticholinergic drug, having a wide spectrum of activity. Hence, the kinetics of oxidation of ASM by diperiodatocuperate (DPC) in the presence of micro (10-6) amounts of Ru(III) catalyst has been investigated spectrophotometrically in aqueous alkaline medium at I = 0.50 mol dm-3. The reaction between DPC and ASM exhibits 1:2 stoichiometry (ASM:DPC) i. e., one mole of ASM require two moles of DPC to give products. The main oxidation products were confirmed by spectral studies. The reaction is first order with respect to [DPC] and [Ru(III)], while the order with respect to [ASM] and [OH-] was less than unity. The rates decreased with increase in periodate concentration. The reaction rates revealed that Ru(III) catalyzed reaction was about seven-fold faster than the uncatalyzed reaction. The catalytic constant (KC) was also determined at different temperatures. A plausible mechanism is proposed. The activation parameters with respect to slow step of the mechanism were calculated and the thermodynamic quantities were also determined. Kinetic experiments suggest that [Cu(H 2IO6)(H2O)2] is the reactive Cu(III) species and [Ru(H2O)5OH]2+ is the reactive Ru(III) species.
A METHOD FOR THE N-DEMETHYLATION OF N-METHYL HETEROCYCLES
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Page/Page column 42, (2011/04/19)
The present invention provides methods of N-demethylating, N-methylated heterocycles and N-methyl, N-oxide heterocycles using a transition metal with an oxidation state of zero, ferrocene or substituted derivatives thereof, or Cr 3+ .N-demethylated heterocycles prepared by the methods of the present invention are also provided.
N-Demethylation of N-methyl alkaloids with ferrocene
Kok, Gaik B.,Scammells, Peter J.
supporting information; experimental part, p. 4499 - 4502 (2010/09/15)
Under Polonovski-type conditions, ferrocene has been found to be a convenient and efficient catalyst for the N-demethylation of a number of N-methyl alkaloids such as opiates and tropanes. By judicious choice of solvent, good yields have been obtained for dextromethorphan, codeine methyl ether, and thebaine. The current methodology is also successful for the N-demethylation of morphine, oripavine, and tropane alkaloids, producing the corresponding N-nor compounds in reasonable yields. Key pharmaceutical intermediates such oxycodone and oxymorphone are also readily N-demethylated using this approach.
Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura
Boswell, Henry D.,Draì?ger, Birgit,McLauchlan, W. Russell,Portsteffen, Andreas,Robins, David J.,Robins, Richard J.,Walton, Nicholas J.
, p. 871 - 878 (2007/10/03)
The enzymes N-methylputrescine oxidase (MPO), the tropine-forming tropinone reductase (TRI), the pseudotropine-forming tropinone reductase (TRII), the tropine:acyl-CoA transferase (TAT) and the pseudotropine:acyl-CoA transferase (PAT) extracted from transformed root cultures of Datura stramonium and a Brugmansia candida x aurea hybrid were tested for their ability to accept a range of alternative substrates. MPO activity was tested with N-alkylputrescines and N-alkylcadaverines as substrates. TRI and TRII reduction was tested against a series of N-alkylnortropinones, N- alkylnorpelletierines and structurally related ketones as substrates. TAT and PAT esterification tests used a series of N-substituted tropines, pseudotropines, pelletierinols and pseudopelletierinols as substrates to assess the formation of their respective acetyl and tigloyl esters. The results generally show that these enzymes will accept alien substrates to varying degrees. Such studies may shed some light on the overall topology of the active sites of the enzymes concerned.
