Nomifensine

Base Information

• Chemical Name: Nomifensine
• CAS No.: 24526-64-5
• Deprecated CAS: 89664-19-7,118184-50-2
• Molecular Formula: C16H18 N2
• Molecular Weight: 238.332
• Hs Code.: 2933499090
• UNII: 1LGS5JRP31
• DSSTox Substance ID: DTXSID0023377
• Nikkaji Number: J16.715K
• Wikipedia: Nomifensine
• Wikidata: Q409948
• NCI Thesaurus Code: C72824
• Pharos Ligand ID: YWQMVTC9H71T
• Metabolomics Workbench ID: 143614
• ChEMBL ID: CHEMBL273575
• Mol file: 24526-64-5.mol

Synonyms:Hoe 984;Hoe-984;Hoe984;Linamiphen;Maleate, Nomifensine;Merital;Nomifensin;Nomifensine;Nomifensine Maleate;Nomifensine Maleate (1:1)

Chemical Property of Nomifensine

Chemical Property:

• Vapor Pressure: 6.28E-06mmHg at 25°C
• Melting Point: 179-181°
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 378.4°Cat760mmHg
• PKA: 7.85±0.40(Predicted)
• Flash Point: 164°C
• PSA: 29.26000
• Density: 1.114g/cm³
• LogP: 3.36520
• Storage Temp.: 2-8°C(protect from light)
• 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:

98%,99%, ^*data from raw suppliers

2-Methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: CN1CC(C2=C(C1)C(=CC=C2)N)C3=CC=CC=C3
• Description: Nomifensine is an inhibitor of norepinephrine (NE) and dopamine (DA) reuptake. It inhibits uptake of NE, DA, and serotonin (5-HT) in rat brain synaptosomes with IC50 values of 6.6, 48, and 830 nM, respectively. It is selective for DA, NE, and 5-HT uptake inhibition over binding to dopamine D2, α1- adrenergic-, 5-HT2, and muscarinic receptors (IC50s = 43,000, 1,200, 3,800, and >13,000 nM, respectively, in rat brain membranes). Nomifensine is selective for inhibition of NE over DA uptake in vivo with minimal inhibitory doses of 28 and less than 57 μmol/kg, respectively. It decreases the time Wistar Kyoto, but not Sprague-Dawley, rats spend immobile in the forced swim test but also increases locomotor activity in the open field test in Wistar Kyoto and Sprague-Dawley rats when administered at a chronic dose of 10 mg/kg.
• Uses: A novel antidepressant distinguished from existing tricyclic and tetracyclic antidepressants by its bicyclic structure.
• Therapeutic Function: Psychostimulant

Technology Process of Nomifensine

There total 14 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:

N-(2-Aminobenzyl)-2-(methylamino)-1-phenyl-1-ethanol (65514-97-8) → nomifensine (24526-64-5)

Guidance literature:

With hydrogenchloride; sulfuric acid; zinc; Yield given. Multistep reaction; 1) EtOH, 0 - 5 deg C, 2) CH₂Cl₂, r.t., 10 - 12 h;

DOI:10.1055/s-1990-26846

Reference yield:

(2-nitrobenzyl)methylamine (56222-08-3) → nomifensine (24526-64-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / triethylamine / diethyl ether / 4 h / 18 - 25 °C

2: 88 percent / NaBH₄ / methanol; H₂O / 4 h / Ambient temperature

3: 87 percent / H₂ / Raney nickel / ethanol / 12 h / 760 Torr

4: conc. H₂SO₄ / CH₂Cl₂ / 0.5 h / 6 - 8 °C

With sodium tetrahydroborate; sulfuric acid; hydrogen; triethylamine; nickel; In methanol; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jm00157a012

Reference yield:

2-acetophenone (102436-67-9) → nomifensine (24526-64-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / NaBH₄ / methanol; H₂O / 4 h / Ambient temperature

2: 87 percent / H₂ / Raney nickel / ethanol / 12 h / 760 Torr

3: conc. H₂SO₄ / CH₂Cl₂ / 0.5 h / 6 - 8 °C

With sodium tetrahydroborate; sulfuric acid; hydrogen; nickel; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/jm00157a012

upstream raw materials:

styrene oxide

(2-nitrobenzyl)methylamine

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

2-acetophenone

Downstream raw materials:

N-(2-Methyl-4-phenyl-1,2,3,4-tetrahydro-8-isochinolyl)-acetamid

8-(N'-chloroacetylureido)-4-phenyl-2-methyl-1,2,3,4-tetrahydroisoquinoline

4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline

2-Methyl-4-phenyl-8-chlor-1,2,3,4-tetrahydroisochinolin hydrogenmaleat

Refernces

• 1、 Venkov, Atanas P.,Vodenicharov, Daniel M.. "A New Synthesis of 1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines". . p. 253 - 255. Retrieved 2007/10/02.
• 2、 Zara-Kaczian, E.,Gyoergy, L.,Deak, G.,Seregi, A.,Doda, M.. "Synthesis and Pharmacological Evaluation of Some New Tetrahydroisoquinoline Derivatives Inhibiting Dopamine Uptake and/or Possessing a Dopaminomimetic Property". . p. 1189 - 1195. Retrieved 2007/10/02.