Synthesizing Diazeniumdiolates from Primary Amines as Nitroxyl Donors

Abstract

The use of Nitroxyl (HNO) donors has been shown to have a multitude of pharmaceutical and medicinal uses, ranging from slowing tumor growth to treatment of alcoholism. Primary amine based diazeniumdiolates, also known as NONOates, are extensively used in biochemical, physiological and pharmacological studies due to their ability to slowly release Nitroxyl (HNO.). While their counterpart, secondary amine based diazeniumdiolates can slowly release nitric oxide (NO). Herein, we report the synthesis, characterization and chemical properties of several primary amine-based diazeniumdiolates. These compounds extend the range of known diazeniumdiolate-based HNO donors. For our study, the primary amines we used were: Isopropylamine, Cyclopentylamine and 4-methylcyclohexylamine. Faculty Sponsor: Cory DiCarl