(+)-Nomifensine

Base Information

• Chemical Name: (+)-Nomifensine
• CAS No.: 89664-20-0
• Molecular Formula: C16H18N2
• Molecular Weight: 238.332
• UNII: 37W6H6V7ST
• ChEMBL ID: CHEMBL400964
• DSSTox Substance ID: DTXSID801316945
• Metabolomics Workbench ID: 67007
• Pharos Ligand ID: YWQTMK6AJPVF
• Mol file: 89664-20-0.mol

Synonyms:(+)-Nomifensine;(R)-Nomifensine;(+)-Nomiphensine;89664-20-0;Nomifensine, (R)-;37W6H6V7ST;CHEMBL400964;CHEBI:521391;(4R)-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine;(R)-1,2,3,4-Tetrahydro-2-methyl-4-phenyl-8-isoquinolinamine;(4R)-2-methyl-4-phenyl-3,4-dihydro-1H-isoquinolin-8-amine;8-ISOQUINOLINAMINE, 1,2,3,4-TETRAHYDRO-2-METHYL-4-PHENYL-, (R)-;UNII-37W6H6V7ST;SCHEMBL125020;DTXSID801316945;BDBM50426364;(4R)-1,2,3,4-TETRAHYDRO-2-METHYL-4-PHENYL-8-ISOQUINOLINAMINE;BRN 6064059;EN300-27118123;Q27225764;8-Isoquinolinamine, 1,2,3,4-tetrahydro-2-methyl-4-phenyl-, (4R)-

Chemical Property of (+)-Nomifensine

Chemical Property:

• Melting Point: 179-181oC
• PSA: 29.26000
• LogP: 3.36520
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 238.146998583
• Heavy Atom Count: 18
• Complexity: 272

Purity/Quality:

99% ^*data from raw suppliers

Nomifensine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC(C2=C(C1)C(=CC=C2)N)C3=CC=CC=C3
• Isomeric SMILES: CN1C[C@@H](C2=C(C1)C(=CC=C2)N)C3=CC=CC=C3
• Uses: A novel labelled antidepressant distinguished from existing tricyclic and tetracyclic antidepressants by its bicyclic structure.

Technology Process of (+)-Nomifensine

There total 8 articles about (+)-Nomifensine 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: 100.0%

oxomorpholine → (R)-(-)-2-Methyl-4-phenyl-8-amino-1,2,3,4-tetrahydroisochinolin (89664-20-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; for 14h; under 775.743 Torr;

Reference yield:

nomifensine (24526-64-5) → (R)-(-)-2-Methyl-4-phenyl-8-amino-1,2,3,4-tetrahydroisochinolin (89664-20-0) + (S)-(+)-2-Methyl-4-phenyl-8-amino-1,2,3,4-tetrahydroisochinolin (89664-18-6)

Guidance literature:

With Chiracel AD column; In hexane; isopropyl alcohol; Resolution of racemate;

DOI:10.1016/j.bmcl.2012.09.050

Reference yield:

2-[(2-Amino-benzyl)-methyl-amino]-1-phenyl-ethanone (119810-30-9) → (R)-(-)-2-Methyl-4-phenyl-8-amino-1,2,3,4-tetrahydroisochinolin (89664-20-0) + (S)-(+)-2-Methyl-4-phenyl-8-amino-1,2,3,4-tetrahydroisochinolin (89664-18-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / ethanol / 1.5 h / 0 - 20 °C

2: sulfuric acid / dichloromethane / 0.33 h / 0 - 20 °C

3: Chiracel? AD column / hexane; isopropyl alcohol / Resolution of racemate

With sodium tetrahydroborate; sulfuric acid; In ethanol; hexane; dichloromethane; isopropyl alcohol;

DOI:10.1016/j.bmcl.2012.09.050

upstream raw materials:

nomifensine

2-[(2-Amino-benzyl)-methyl-amino]-1-phenyl-ethanone

N-(2-Aminobenzyl)-2-(methylamino)-1-phenyl-1-ethanol

o-aminobenzaldehyde

Downstream raw materials:

(R)-(-)-2-Methyl-4-phenyl-8-ethoxycarbonylamino-1,2,3,4-tetrahydroisochinolin