Kinetics of photooxidation of papaverine hydrochloride and its major photooxidation products

Abstract

HPCE methodology was modified to be used in kinetic experiments on photooxidation reactions of papaverine hydrochloride 1 and its oxidation products (papaverinol 2 and papaveraldine hydrochloride 3) chloroform solutions exposed to UV 254 light in aerobic conditions. On photooxygenation of the above compounds is formed the final degradation product, a brown compound X 4, 2,3,9,10-tetramethoxy-12-oxo-12 H-indolo[2,1- a]isoquinolinylim chloride. The rate of 4 formation from the above compounds can be given as 2 > 3 > 1 > 1 HCl. The photooxidation reactions of 1 and 2 proceed with pseudo first-order kinetics and that reaction for 3 follows zero-order kinetics. The most labile compound is 2 whose half-life time is 2.4 times shorter than that one of 1 HCL. The most stable product is 3 whose half-life time is 31-fold longer than of 2. The specific quantum yields are equal 0.28, 0.30 and 0.10 for 1 HCl, 2 and 3, respectively which confirm the above stability pattern of the compounds concerned.