Primaquine Metabolite Synthesis and Analysis

Acetonitrile and methanol of HPLC-grade were obtained from Fisher Scientific (Fair Lawn, NJ, USA). Water was purified in a Milli-Q system (Millipore, Bedford, MA, USA). Primaquine diphosphate and formic acid were purchased from Sigma (St Louis, MO, USA). Carboxyprimaquine (cPQ) was prepared using the procedure reported by McChesney and Sarangan [32 (link)]. Primaquine alcohol, 2-hydroxyprimaquine, 3-hydroxyprimaquine, 4-hydroxyprimaquine, 5-hydroxyprimaquine, primaquine-5,6-ortho-quinone, primaquine N-carbamoyl glucuronide, primaquine methyl carbamate, carboxy primaquine lactam, carboxy primaquine methyl ester and primaquine N-acetate were synthesized at National Center for Natural Products Research (NCNPR) and their identity and purity were confirmed by spectral data (IR, NMR and High-Resolution MS) and comparison of their physical data (m.p.) with published values [20 (link), 21 (link)].