112885-41-3

A poison by ingestion.

Mosapride citrate, a new gastroprokinetic benzamide was introduced in Japan as Gasmotin for the relief of gastrointestinal symptoms in patients with chronic gastritis, gastro-oesophageal reflux, dyspepsia and post-surgery use. Mosapride is synthesized by final amidation between the corresponding benzoic acid, itself obtained in 3 steps from methyl 4-acetamido salicylate, and the appropriate 2-aminomethyl-morpholine. Mosapride is a 5-HT4 partial agonist without notable activity for D2, 5-HT1 , 5-HT2, alpha-1 and alpha-2 receptors. In dogs, mosapride was as potent as cisapride to stimulate antral and duodenal motility. In most of species including man, mosapride undergoes extensive cleavage to a N-debenzylated metabolite which retains partial 5-HT4 activity but has potent 5-HT3 antagonist activity.

White to Off-White Crystalline Solid

Dainippon (Japan)

A selective 5-HT4 receptor agonist. Gastroprokinetic.

gastroprokinetic agent

ChEBI: Mosapride is a racemate comprising equimolar amounts of (R)- and (S)-mosapride. It is a gastroprokinetic agent which acts on 5-hydroxytryptamine type 4 (5-HT4) receptors in the gastrointestinal plexus, consequently increasing the release of acetylcholine and hence enhancing gastrointestinal motility and gastric emptying. It has a role as a gastrointestinal drug and a serotonergic agonist. It contains a (R)-mosapride and a (S)-mosapride.

Gasmotin

The general procedure for the synthesis of 4-amino-5-chloro-2-ethoxy-N-((4-(4-fluorobenzyl)morpholin-2-yl)methyl)benzamide from compound (CAS: 636582-70-2) was as follows: 12 mL (117%) of aqueous hydrochloric acid was added to a suspension of 1.3 g (2.5 mmol) of compound (VIII) and 3 mL of water. The resulting solution was stirred at 40 °C for 3 h. After cooling to 10 °C, 38 mL of a 4 M aqueous sodium hydroxide solution was added dropwise. The precipitated mosapride base (Formula IX) was filtered and washed twice with water to give 1.05 g (100%) of compound (IX). 1.01 g of compound (IX) obtained above was dissolved in 25 mL of 10% citric acid aqueous solution under stirring, heated to boiling, cooled to 0°C and filtered the precipitated product, washed twice with water to give 1.34 g (86%) of 4-amino-5-chloro-2-ethoxy-N-((4-(4-fluorobenzyl)morpholin-2-yl)methyl)benzamide. Melting point: 110-113°C.

Store at -20°C

[1] Patent: WO2003/106440, 2003, A2. Location in patent: Page 10