Oxidation of Amitriptyline by Bromamine-T in Acidic Buffer Medium: A Kinetic and Mechanistic Approach
Authors: Chandrashekar, R. T. Radhika, B. M. Venkatesha, S. Ananda, Shivalingegowda, T. S. Shashikumar, H. Ramachandra
The kinetics of the oxidation of amitriptyline (AT) by sodium N-bromotoluene sulphonamide (C6H5SO2NBrNa) has been studied in an acidic buffer medium of pH 1.2 at 303 K. The oxidation reaction of AT was followed spectrophotometrically at maximum wavelength, 410 nm. The reaction rate shows a first order dependence each on concentration of AT and concentration of sodium N-bromotoluene sulphonamide. The reaction also shows an inverse fractional order dependence at low or high concentration of HCl. The dielectric constant of the solvent shows negative effect on the rate of reaction. The addition of halide ions and the reduction product of BAT have no significant effect on the rate. The rate is unchanged with the variation in the ionic strength (NaClO4) of the medium. Addition of reaction mixtures to be aqueous acrylamide solution did not initiate polymerization, indicating the absence of free radical species. The stoichiometry of the reaction was found to be 1:1 and oxidation product of AT is identified. The Michaelis-Menton type of kinetics has been proposed. The CH3C6H5SO2NHBr has been assumed to be the reactive oxidizing species. Thermodynamical parameters were computed by studying the reactions at different temperatures. A mechanism consistent with observed kinetics is presented.
Keywords: Amitriptyline, bromamine-T, kinetics, oxidation.
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 Barbuic, Hotopf M “Amitriptyline V, the rest: still the leading antidepressant after 40 years of randomized controlled trails”. The British Journal of psychiatry: The Journal of Mental science 178(2):129-144, (2001).
 Amitriptyline hydrochloride “The American society of health-system pharmacists, http://www.drugs.com/monograph/Amitriptyline-hydrochloride.html. Retrieved 3, (2011).
 S. G. Hubscher, Functional biliary type pain Syndrome. In P.J. Pasricha, W. D. Willis and G.F Gebhart (Eds) ‘Italics chronic abdominal and visceral pain. ‘Italics” London: Informa health care, pp.459-461, (2006).
 Breyer-Pfaff Ursula, Drug Metabolism and Disposition, 28(8), 869-872 (2000).
 Breyer-Pfaff Ursula, Drug Metabolism reviews, 36 (3-4): 723-746 (2004).
 Zhou Diansong Guo, J. Jian Linnenbach Alban, L. Booth Genthe Catherine and W Grimm Scott., Drug Metabolism and Disposition, 38 (5), 863-870 (2010).
 C. Abbar Jyothi, D. Lamani Shekappa and T. Nandibewoor Sharnappa, Ruthenium(III) Catalyzed Oxidative Degradation of Amitriptyline-A Tricyclic Antidepressant Drug by Permanganate in Aqueous Acidic Medium., Journal of Solution Chemistry 40 (3) 502-520 (2011).
 B. Ledesma, S. Roman, J. F. Gonzalez, F. Zamora and Rayo M.C., Study of the Mechanisms Involved in the Adsorption of Amitriptyline from Aqueous Solution onto Activated Carbons Adsorption Science and Technology, 28 (8/9), 739-750, (2010).
 R. Vijaya, T. Jayaraj, Pratheeba, A. Anuzvi and K. Ruckmani. Formulation and Evaluation of Transdermal Drug Delivery System of Simvastatin. Journal of Pharamacy Research, 4 (6) 1748-1750, (2011).
 D. Lamani Shekappa and S.T Nandibewoor. Journal of Thermodynamics and Catalysis, 2 (2) 110, (2011).
 Jang: Liu, X, Chan, C. Weinshenker, D. Hall. R, Xiao, G. Ye,K “Amitriptyline is a TrKA and TrKB receptor agoinist that promotes TrKA TrKB heterodimerization and has potent neurotrophic activity” chemistry and biology, 16(6) 644-656, (2009).
 Mahadevappa. D. S. Ananda. S. Murthy. A. S. A and Rangappa. K. S., Tetrahedron, 10, 1673 (1984).
 P. V. S. Rao, K. V Subbaiah and P. S. N Murthy. Reaction kinet catol, lett., 10, 79, (1979), 11, 287 (1979).
 S. Ananda, B. M. Venkatesha, D. S. Mahadevappa and N. M. Madegowda. Indian J. chem., 30A, 789-792 (1991).
 Chandrashekar, B. M. Venkatesha, S. Ananda, Research Journal of Chemical Sciences 2 (8), 26-30 (2012).
 F. Ruff and Kucsman ‘Oxidation of dialkyl sulphides with BAT in alkaline buffer solutions. Journal of the Chemical society. Perkin Transactions, II, p.1075, (1990).
 D.S. Mahadevappa and Puttaswamy, ‘Kinetics of Oxidation of aliphatic ketones with bromamine-T in acid medium. Bulletin of the Chemical Society of Japan, Vol.61, No.2, pp.543-547, (1988).
 Chandrashekar, B.M. Venkatesha, S. Ananda and N.M. Madegowda. Kinetic and mechanistic study of oxidation of piperazines by bromamine-T in acidic medium. Modern Research in Catalysis, 2, 157-163, (2013).
 Puttaswamy, R. Ramachandrappa. Ruthenium(III) catalysed reactions oxidation of substituted ethanols by BAT in hydrochloric acid medium ‘Transition Metal Chemistry, Vol. 24, No.3, pp, 326-332, (1999).
 Chandrashekar R. T, Radhika, B. M. Venkatesha And S. Ananda. Kinetics and mechanistic, study of oxidation of Nicotinamide by bromamine-T in hydrochloric acid medium catalysed by Ru(III) ion. International Journal of Current Research vol6, issue 01, 2014, pp 4567-4571, (2014).
 C. G. R. Nair and P. Indrasenan, New redox titratants in aqueous or partially aqueous media-VI1 ‘Potentiometric determinations using dibromamine-T and some further applications of dichloramine-T. Talanta, Vol.23, No.3, pp 239-241 (1976).
 J. C. Morris, J.A. Salazar and M.A., Wineman. J. Ame. Chem. Soc, 70, 2036 (1948).
 D. S Mahadevappa and N.M Madegowda. Estimation of glutathione with Chloramine-T and dichloramine-T, Talanta, Vol,22, No.9, pp 771-773, (1975).
 B. G. Pryde, F. G. Soper, Journal of Chem. Soc., 1582, (1926).
 E Bishop and V.J. Jennings. ‘Titrimetric analysis with chloramine-T. The status of Chloramine-T as a titrimetric reagent. Talanta, Vol,1, No.3, PP 197-212, (1958).
 F. F Hardy and Johnston, ‘The interactions of N-bromo-N-Sodiobenzenesulphonamide (bromamine-B) with p-nitrophenoxide ion. Journal of the Chemical Society, perkin Trasections II, No.6, pp.742-746 (1973).