Nemonapride

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Nemonapride
Nemonapride.png
Systematic (IUPAC) name
N-(1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
  • (Prescription only)
Routes of
administration
Oral
Identifiers
CAS Registry Number 75272-39-8
ATC code None
PubChem CID: 4452
IUPHAR/BPS 983
UNII Q88T5P3444 YesY
KEGG D01468 YesY
Chemical data
Formula C21H26ClN3O2
Molecular mass 387.90 g/mol
 YesY (what is this?)  (verify)

Nemonapride (Emilace) is an atypical antipsychotic approved in Japan for the treatment of schizophrenia. It was launched by Yamanouchi in 1991. Nemonapride acts as a D2 and D3 receptor antagonist, and is also a potent 5-HT1A receptor agonist. It has affinity for sigma receptors.

Synthesis[edit]

Nemonapride synthesis:[1][2]

5-Chloro-2-methoxy-4-(methylamino)benzoic acid (1) is acylated with Ethyl chloroformate to give the mixed anhydride; Amidation then occurs in a second step via reaction with 3-amino-1-benzyl-2-methylpyrrolidine to give Nemonapride (2).

See also[edit]

References[edit]

  1. ^ M. Takashima et al., JP Kokai 79 14965; eidem, U.S. Patent 4,210,660 (1979, 1980 both to Yamanouchi).
  2. ^ doi:10.1021/jm00142a019
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