Adatanserin

Adatanserin (WY-50,324, SEB-324) is a mixed 5-HT1A receptor partial agonist and 5-HT2A and 5-HT2C receptor antagonist. It was under development by Wyeth as an antidepressant but was ultimately not pursued.

Adantaserin has been shown to be neuroprotective against ischemia-induced glutamatergic excitotoxicity, an effect which appears to be mediated by blockade of the 5-HT2A receptor.

Synthesis

 * Adatanserin synthesis.svg

2-Chloropyrimidine (1) reacts with piperazine (2), forming 2-(1-piperazinyl)pyrimidine (3). Treatment with the phthalimide derivative N-(2-bromoethyl)phthalimide (4) in an alkylation reaction produces (5), which is deprotected using hydrazine to give the primary amine (6). Amide formation with the acid chloride of 1-adamantanecarboxylic acid yields adatanserin.