Nemonapride

Base Information

• Chemical Name: Nemonapride
• CAS No.: 75272-39-8
• Deprecated CAS: 93664-94-9
• Molecular Formula: C21H26 Cl N3 O2
• Molecular Weight: 387.909
• European Community (EC) Number: 689-004-7
• UNII: Q88T5P3444
• DSSTox Substance ID: DTXSID601116422
• Nikkaji Number: J257.592B
• Wikipedia: Nemonapride
• NCI Thesaurus Code: C73036
• Pharos Ligand ID: LYH5ZBPNWYVY
• Metabolomics Workbench ID: 63246
• Mol file: 75272-39-8.mol

Synonyms:cis-N-(1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-methylaminobenzamide;emonapride;nemonapride;nemonapride, (cis)-isomer;YM 09151-2;YM 09151-M;YM-09151-2

Chemical Property of Nemonapride

Chemical Property:

• Vapor Pressure: 1.03E-10mmHg at 25°C
• Melting Point: 152-153°C
• Boiling Point: 514.9°C at 760 mmHg
• Flash Point: 265.2°C
• PSA: 53.60000
• Density: 1.23g/cm³
• LogP: 4.18490
• Storage Temp.: Store at RT
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 387.1713548
• Heavy Atom Count: 27
• Complexity: 486

Purity/Quality:

98%Min ^*data from raw suppliers

Nemonapride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(CCN1CC2=CC=CC=C2)NC(=O)C3=CC(=C(C=C3OC)NC)Cl
• Isomeric SMILES: C[C@@H]1[C@@H](CCN1CC2=CC=CC=C2)NC(=O)C3=CC(=C(C=C3OC)NC)Cl
• Description: Nemonapride is a potent dopamine D2receptor antagonist antipsychotic reported to have superior efficacy against hallucinations and delusions and also to be effective in the treatment of negative symptoms. The compound is a benzamide diastereomer and, although more potent than haloperidol, side effects are reported to be few primarily akinesia and some muscle rigidity with extrapyramidal symptoms being rare. Nemonapride is an antipsychotic that readily passes through the blood brain barrier and exhibits potent neuroleptic effects in animals. It binds dopamine 2 (D2)-like receptors preferentially over D1-like receptors (Kis = 0.06, 0.3, and 0.15 nM for D2, D3, and D4, respectively). Nemonapride also binds sigma 1 (σ1) and σ2 receptors (Kis = 8.4 and 9.6 nM, respectively) and activates the serotonin 1A receptor (5-HT1A; IC50 = 34 nM).
• Uses: Nemonapride is a selective dopamine D2 receptor antagonist. Nemonapride is used as an antipsychotic. A selective dopamine D2 receptor antagonist. Used as an antipsychotic

Technology Process of Nemonapride

There total 28 articles about Nemonapride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 51.0%

(2S,3S)-3-azido-1-benzyl-2-methylpyrrolidine (1337862-77-7) + 5-chloro-2-methoxy-4-(methylamino)benzoic acid (61694-98-2) → N-((2S,3S)-1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide (75272-39-8)

Guidance literature:

(2S,3S)-3-azido-1-benzyl-2-methylpyrrolidine; With hydrogen; In methanol; at 20 ℃;

5-chloro-2-methoxy-4-(methylamino)benzoic acid; With chloroformic acid ethyl ester; triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1248/cpb.c16-00568

Reference yield:

1-benzyl-3-(hydroxyimino)-2-methylpyrrolidine (74880-17-4) → N-((2S,3R)-1-Benzyl-2-methyl-pyrrolidin-3-yl)-5-chloro-2-methoxy-4-methylamino-benzamide (70325-83-6,75272-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, aq. ammonia / Raney nickel / methanol; ethanol / 5 °C

2: CH₂Cl₂ / 2 h / Ambient temperature

With ammonium hydroxide; hydrogen; nickel; In methanol; ethanol; dichloromethane;

DOI:10.1021/jm00142a019

Reference yield:

1-benzyl-3-(hydroxyimino)-2-methylpyrrolidine (74880-17-4) → Emilace (70325-83-6,75272-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, aq. ammonia / Raney nickel / methanol; ethanol / 5 °C

2: CH₂Cl₂ / 2 h / Ambient temperature

With ammonium hydroxide; hydrogen; nickel; In methanol; ethanol; dichloromethane;

DOI:10.1021/jm00142a019

upstream raw materials:

trans-3-amino-1-benzyl-2-methylpyrrolidine

5-chloro-2-methoxy-4-(methylamino)benzoic acid

5-chloro-2-methoxy-4-(methylamino)benzoic acid methyl ester

1-benzyl-3-(hydroxyimino)-2-methylpyrrolidine

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