Chemical Properties
Crystallized from acetone, melting point 139°C. Acute toxicity LD50 in mice (5 days) (mg/kg): 92.7 by intravenous injection. Alizapride hydrochloride: C16H21N5O2·HCl. [59338-87-3]. Crystallized from methanol-methyl ethyl ketone, melting point 206-208°C.
Originator
Plitican ,Delagrange ,France ,1981
Uses
Alizapride is a strong antiemetic, well-absorbed, and potent, capable of antagonizing vomiting caused by apomorphine and dihydroergotamine, but with weak central nervous system depressant effects and no cholinergic effects. It is used to prevent and treat nausea and vomiting induced by chemotherapy for cancer.
Definition
ChEBI: 6-methoxy-N-[(1-prop-2-enyl-2-pyrrolidinyl)methyl]-2H-benzotriazole-5-carboxamide is a member of benzotriazoles.
Manufacturing Process
38.6 g (0.2 mol) of 2-methoxy-4,5-azimidobenzoic acid were dissolved in
anhydrous toluene and 56 g (0.4 mol) of 1-allyl-2-amino-methylpyrrolidine
were added. The mixture was heated to 50°C and then 42 g (0.3 mol) of
phosphoric anhydride were added. The mixture was warmed at reflux
temperature for 3 hours and then cooled to 80°C. After adding water, the
aqueous layer was alkalized. The crystals were filtered, washed with water
and then dissolved in 450 ml of acetone. After crystallization, the product was 40.4 g (yield 65%) of N-(1'-allyl-2'-pyrrolidylmethyl)-2-methoxy-4,5-
azimidobenzamide having a melting point of 139°C were obtained.
Therapeutic Function
Neuroleptic, Antiemetic
