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. Can. J. Chem. 66, 1566Chem. 66, (1988. The basic hydrolysis of diazepam and several N-alkyl nitrazepam derivatives has been studied in the presence of reactive counterion micelles of cetyltrimethylammonium hydroxide (CTAOH) and vesicles of didodecyldimethylarnmonium hydroxide (DDAOH). In both surfactants, the rate of hydrolysis of all compounds was found to be dependent on the hydroxide concentration at constant surfactant concentration and this was interpreted as evidence for initial amide hydrolysis. The hydrolysis in CTAOH was inhibited by added salts in the order Br-< NO3-< so4'-. At concentrations above 3 mM surfactant, the rate of hydrolysis of each compound was similar in CTAOH and in DDAOH. At lower concentrations of CTAOH, however, the rate of hydrolysis was significantly lower than that in DDAOH. On the basis of this evidence, it was concluded that the cmc of CTAOH was between 2-3 mM, which is in good agreement with the value of 1.8 mM obtained by Zana from conductivity measurements. For diazepam, a mechanistic change is indicated on transfer from water to either micelles or vesicles and since vesicles are considered good models of biological membranes, this suggests that conclusions concerning the bioavailability of diazepam should not be based on studies in water but rather on studies in either micelles or vesicles. puisque les vCsicules sont considCrCes comme de bons modeles des membranes biologiques, il est suggCrC que les conclusions concernant la bio-disponibilitk du diazepam ne devraient pas 6tre basCes sur des Ctudes dans l'eau mais plutbt sur des Ctudes dans des micelles ou dans des v6sicules.[Traduit par la revue]

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The rate of the hydrolysis of (I) increases in both micellar and vesicular solution on enhancement of the concentrations of NaOH or the detergent.