| Identification | More | [Name]
4-Amino-5-chloro-2-ethoxy-N-((4-(4-fluorobenzyl)-2-morpholinyl)methyl)benzamide | [CAS]
112885-41-3 | [Synonyms]
4-AMINO-5-CHLORO-2-ETHOXY-N-((4-(4-FLUOROBENZYL)-2-MORPHOLINYL)METHYL)BENZAMIDE
4-AMINO-5-CHLORO-2-ETHOXY-N-[4-(4-FLUORO-BENZYL)-MORPHOLIN-2-YLMETHYL]-BENZAMIDE
4-AMINO-5-CHLORO-2-ETHOXY-N-[[[4-(4-FLUOROPHENYL)METHYL]-2-MORPHOLINYL]METHYL]-BENZAMIDE
MOSAPRIDE
((4-(4-fluorobenzyl)-2-morpholinyl)methyl)benzamide/mosapride
4-Amino-5-Chloro-2-Ethoxy-N-((4-(4-Fluorobenzyl)-2-Morpholinyl)Methyl)Benzamide/Mosapride | [Molecular Formula]
C21H25ClFN3O3 | [MDL Number]
MFCD00867430 | [Molecular Weight]
421.89 | [MOL File]
112885-41-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White to Off-White Crystalline Solid | [Melting point ]
151-153°C | [Boiling point ]
549.2±50.0 °C(Predicted) | [density ]
1.272±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.52±0.46(Predicted) | [color ]
White to Off-White | [Usage]
a selective 5-HT4 receptor agonist | [CAS DataBase Reference]
112885-41-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Hazard]
A poison by ingestion. | [Description]
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. | [Chemical Properties]
White to Off-White Crystalline Solid | [Originator]
Dainippon (Japan) | [Uses]
A selective 5-HT4 receptor agonist. Gastroprokinetic. | [Uses]
gastroprokinetic agent | [Definition]
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. | [Brand name]
Gasmotin | [Synthesis]
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. | [storage]
Store at -20°C | [References]
[1] Patent: WO2003/106440, 2003, A2. Location in patent: Page 10 |
| Safety Data | Back Directory | [Safety Profile]
A poison by ingestion.
When heated to decomposition it emits
toxic vapors of NOx, F-, and Cl-. |
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