Improved Delivery Through Biological Membranes. XVII. A Site-Specific Chemical Delivery System as a Short-Acting Mydriatic Agent.

O,O-Di(ethylsuccinyl) adrenalone was synthesized and studied as a potential short-acting mydriatic agent. This unsymmetrical tetraester has a very short hydrolytic half-life in biological fluids (approximately 1 minute). The hydrolysis produces the inactive adrenalone. On the other hand, a reduction-hydrolytic sequence resulting in adrenaline was established as the mechanism of action of these types of compounds. The facile activation to epinephrine and fast deactivation to adrenalone of the unreduced chemical delivery system results in a short-acting mydriatic agent, a potentially important diagnostic or surgical agent.