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 Dopamine [receptor D2|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.