title: Rapid aromatic hydrogen exchange in the antimalarial primaquine.
abstract: Primaquine, an 8-aminoquinoline antimalarial, is shown to undergo unexpectedly rapid aromatic proton exchange with the medium. At a pH less than 4, the exchange of C-5 is so fast as to be unmeasurable by proton nmr methods. At a pH of 6-6.5 the half-time for exchange is 4 to 5 minutes. This unexpectedly high rate of exchange of a carbon-proton with medium may provide an important clue to the biological activity of primaquine.
authors.affiliation: The Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS, 38677.
authors.forename: J D
authors.initials: JD
authors.lastname: McChesney
authors.forename: S
authors.initials: S
authors.lastname: Sarangan