Tag: Umespirone

What is Umespirone?

Published on by Andrew Marshall1 Comment

Introduction

Umespirone (KC-9172) is a drug of the azapirone class which possesses anxiolytic and antipsychotic properties.

Outline

It behaves as a 5-HT1A receptor partial agonist (Ki = 15 nM), D2 receptor partial agonist (Ki = 23 nM), and α1-adrenoceptor receptor antagonist (Ki = 14 nM), and also has weak affinity for the sigma receptor (Ki = 558 nM).

Unlike many other anxiolytics and antipsychotics, umespirone produces minimal sedation, cognitive/memory impairment, catalepsy, and extrapyramidal symptoms.

Synthesis

The condensation between ethyl cyanoacetate and acetone gives ethylisopropylidenecyanoacetate 759-58-0. This product is reacted with N-butylcyanoacetamide 39581-21-0 in sodium methoxide solution to give N-butyl-2,4-dicyano-3,3-dimethylglutarimide, CID:10681941. The glutarimide is cyclized with phosphoric acid to yield 3-butyl-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone, https://pubchem.ncbi.nlm.nih.gov/compound/10825633 CID:10825633.

The reaction between 1-(o-anisyl)piperazine 35386-24-4 and 1,4-dibromobutane 110-52-1 gives the Quat salt CID:15895413.

Convergent synthesis (in the presence of potassium carbonate) affords Umespirone (KC-9172).

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