Alizapride

Alizapride is a dopamine antagonist with prokinetic and antiemetic effects used in the treatment of nausea and vomiting, including postoperative nausea and vomiting. It is structurally related to metoclopramide and other benzamides.

Mechanism

Alizapride acts on the vomiting center by blocking D2 dopamine receptors.
Since alizapride is able to cross the blood-brain barrier, adverse effects may include temporary extrapyramidal motor disorders such as acute dystonia and dyskinesia.
It has a plasma half-life of 3 hours.

Synthesis

The synthesis of Alizapride happens in multiple steps:
4-Aminosalicylic acid is first methylated using dimethyl sulfate. A nitro group is then introduced that is reduced using Raney nickel to afford an amino group. The two amino groups are then closed to a triazole ring using sodium nitrite and hydrochloric acid. This is then condensed with 1-allyl-2-aminomethylpyrrolidine to afford Alizapride.