PMID: 1536Jan 1, 1976

Synthesis and adrenoreceptor blocking action of aziridinium ions derived from phenoxybenzamine and dibenamine

Journal of Medicinal Chemistry
J G HenkelP Lewis


Crystalline perchlorate salts of aziridinium ions derived from phenoxybenzamine and dibenamine were prepared. Both aziridinium ions were tested on the rat vas deferens and found to possess alpha-adrenergic potencies which were nearly identical with those of the parent compounds. The hydrolysis rates of phenoxybenzamine and dibenamine aziridinium ions (2a,b) in physiological medium were found to be 6.0 4 x 10(-4) and 8.35 x 10(-4) sec-1, respectively. The rates of cyclization of the parent amines to 2a and 2b in aqueous medium were 1.9 x 10(-2) and 7.2 x 10(-3) sec-1, respectively. The potencies and kinetic profiles indicate that the aziridinium ion is the only active species in alpha-adrenergic blockade. Moreover, differences in potency between phenoxybenzamine and dibenamine appear to be exclusively to a difference in receptor affinity rather than to a difference in intrinsic alkylating ability.


May 1, 1985·Brain Research Bulletin·M WilkinsonD A Wilkinson
Oct 24, 2001·Drug and Alcohol Dependence·K J VarnerW H Soine
Mar 12, 2002·Bioorganic & Medicinal Chemistry·Dario GiardinàCarlo Melchiorre
Nov 16, 2002·Drug Metabolism and Disposition : the Biological Fate of Chemicals·B RegeW H Soine

Related Concepts

Adrenergic alpha-Antagonists
Smooth Muscle
Phenoxybenzamine Hydrochloride
Vas Deferens Structure

Related Feeds

Adrenergic Receptors: Trafficking

Adrenergic receptor trafficking is an active physiological process where adrenergic receptors are relocated from one region of the cell to another or from one type of cell to another. Discover the latest research on adrenergic receptor trafficking here.