10,11-Dihydro-10,11-dihydroxy-5H-dibenz[b, f]azepine-5-carboxamide, a Metabolite of Carbamazepine Isolated from Human and Rat Urine

Abstract

The synthesis of 10,11-dihydro-10,11-dihydroxy-5H-dibenz[b, f]azepine-5-carboxamide from carbamazepine (Tegretol) is described and this is shown to be one of the metabolites of carbamazepine. The extraction procedure is described fully and further details about the metabolic pathway are discussed, in which carbamazepine epoxide is proposed as an intermediate. The synthesis of another possible metabolite, 10,-11-dihydro-10-hydroxy-5H-dibenz[6,f]azepine-5-carboxamide, from carbamazepine epoxide is also described, although this has not been found as a metabolite in urine. The decomposition of 10,11-dihydroxy-10,11-dihydro-5H-dibenz[b, f]azepine-5-carboxamide to acridine-9-carboxaldehyde under glc conditions is also discussed. © 1973, American Chemical Society. All rights reserved.