75272-39-8

Usage

Uses

Used in Pharmaceutical Industry:
Nemonapride is used as an antipsychotic for the treatment of various psychiatric disorders. It acts as a selective dopamine D2 receptor antagonist, providing potent neuroleptic effects in animals. Its preferential binding to D2-like receptors over D1-like receptors, along with its interaction with sigma and serotonin receptors, contributes to its effectiveness in managing hallucinations, delusions, and negative symptoms associated with psychiatric conditions.
Nemonapride is particularly useful in the treatment of schizophrenia and other psychotic disorders due to its ability to alleviate positive symptoms such as hallucinations and delusions, while also addressing negative symptoms like social withdrawal and emotional blunting. Its low incidence of extrapyramidal symptoms and muscle rigidity make it a preferred choice for patients who are sensitive to side effects commonly associated with other antipsychotic medications.

Originator

Yamanouchi (Japan)

Biological Activity

Highly potent dopamine D 2 -like receptor antagonist; selective over D 1 -like receptors (K i values are 0.1 and 740 nM for D 2 -like and D 1 -like receptors respectively). Also potent 5-HT 1A receptor agonist (IC 50 = 34 nM) and has affinity for sigma receptors.

InChI:InChI=1/C21H26ClN3O2/c1-14-18(9-10-25(14)13-15-7-5-4-6-8-15)24-21(26)16-11-17(22)19(23-2)12-20(16)27-3/h4-8,11-12,14,18,23H,9-10,13H2,1-3H3,(H,24,26)

Upstream product

• 764-37-4 (E)-3-penten-1-ol 
• 1337862-77-7 (2S,3S)-3-azido-1-benzyl-2-methylpyrrolidine 
• 61694-98-2 5-chloro-2-methoxy-4-(methylamino)benzoic acid 
• 50403-13-9 (3R,4R)-3,4-epoxypentan-1-ol 
• 324752-71-8 tert-butyl (1S,2R)-2-hydroxy-1-methylpent-4-enylcarbamate 
• 1352347-71-7 C₁₃H₁₉NO₃S 
• 202743-06-4 (4R,5S)-1-benzyl-4-(hydroxy)-5-methylpyrrolidin-2-one 
• 1337862-62-0 tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)hex-5-en-2-ylcarbamate 
• 202743-07-5 (2S,3R)-1-benzyl-2-methylpyrrolidin-3-ol 
• 1337862-76-6 (4R,5S)-1-benzyl-4-(tert-butyldimethylsilyloxy)-5-methylpyrrolidin-2-one 
• 1337862-69-7 (2S,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidine-1-carboxylate 
• 1294446-91-5 (S)-tert-butyl-N-(3-oxohex-5-en-2-yl)carbamate 
• 78775-32-3 methyl 5-chloro-2-methoxy-4-(N-methyl-N-tosylamido)benzoate 
• 78784-42-6 methyl 2-methoxy-4-(N-methyl-N-tosylamido)benzoate 

Relevant academic research and scientific papers

Concise, protecting-group-free synthesis of (+)-nemonapride via Eu(OTf)3-catalyzed aminolysis of 3,4-epoxy alcohol

A concise, protecting-group-free synthesis of the antipsychotic agent (+)-nemonapride has been achieved featuring a europium(III) trifluoromethanesulfonate (Eu(OTf)3)-catalyzed C4 selective aminolysis of a 3,4-epoxy alcohol by benzylamine and a

A facile approach to trans-4,5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine

An efficient approach to trans-4-hydroxylpyrrolidine lactams 1 starting from amino acid is described. The utility of this method has been demonstrated in the synthesis of antipsychotic nemonapride 3 and antiangiogenic streptopyrrolidine 4. Compared four s