Nisoxetine

Base Information

• Chemical Name: Nisoxetine
• CAS No.: 53179-07-0
• Deprecated CAS: 57226-61-6
• Molecular Formula: C17H21 N O2
• Molecular Weight: 271.359
• Hs Code.: 2922299090
• NSC Number: 283481
• UNII: 17NV064B2D
• DSSTox Substance ID: DTXSID0045175
• Wikipedia: Nisoxetine
• Wikidata: Q906885
• NCI Thesaurus Code: C75172
• Pharos Ligand ID: T94MNC9VHVD8
• Metabolomics Workbench ID: 66428
• ChEMBL ID: CHEMBL295467

Synonyms:3-(2-methoxyphenoxy)-N-methyl-3-phenylpropylamine;3-(o-methoxyphenoxy)-N-methyl-3-phenylpropylamine;DL-N-methyl-3-(o-methoxyphenoxy)-N-methyl-3-phenylpropylamine;Lilly 135252;Lilly 94939;LY 135252;LY 94939;LY-135252;N-methyl-gamma-(2-methylphenoxy)phenylpropanolamine;nisoxetine;nisoxetine hydrochloride;nisoxetine hydrochloride, (+-)-isomer;nisoxetine, (+-)-isomer

Chemical Property of Nisoxetine

Chemical Property:

• Vapor Pressure: 9.2E-07mmHg at 25°C
• Refractive Index: 1.547
• Boiling Point: 404.8°Cat760mmHg
• PKA: 10.16±0.10(Predicted)
• Flash Point: 170.6°C
• PSA: 30.49000
• Density: 1.054g/cm³
• LogP: 3.81570
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 271.157228913
• Heavy Atom Count: 20
• Complexity: 253

Purity/Quality:

99% ^*data from raw suppliers

NISOXETINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CNCCC(C1=CC=CC=C1)OC2=CC=CC=C2OC
• Uses: Antidepressant.
• Clinical Use: Nisoxetine was the initial phenoxyphenylpropylamine synthesized in the Lilly research laboratories during the early 1970s from the rearrangement of an oxygen atom in diphenyhydramine, a diphenylmethoxyethylamine, to a phenoxyphenylpropylamine. Nisoxetine was discovered to be a potent and very selective SNRI, with little affinity for other receptors. It underwent clinical studies as an alternative to Lilly's best-selling antidepressant, nortriptyline, but without the adverse effects associated with the tricyclic secondary amines. It was never marketed, however, because of a greater interest in developing its 4-trifluoromethyl analogue, fluoxetine, an SSRI.

Technology Process of Nisoxetine

There total 5 articles about Nisoxetine 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:

3-chloro-1-(o-methoxyphenoxy)propylbenzene (57226-60-5) + methylamine (74-89-5) → nisoxetine (53179-07-0,57226-61-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In methanol; at 80 ℃; for 24h; Sealed tube;

DOI:10.1124/mol.113.091249

Reference yield:

concentrated aqueous sodium hydroxide + 3-chloro-1-(o-methoxyphenoxy)propylbenzene (57226-60-5) → nisoxetine (53179-07-0,57226-61-6)

Guidance literature:

With methylamine; In methanol;

Reference yield:

phenylpropyl chloride (104-52-9) → nisoxetine (53179-07-0,57226-61-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide; dibenzoyl peroxide / chlorobenzene / 4 h / 85 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Sonication; Cooling with ice

2.2: 12 h / 20 °C / Inert atmosphere; Cooling with ice

3.1: tetra-(n-butyl)ammonium iodide; potassium carbonate / methanol / 24 h / 80 °C / Sealed tube

With N-Bromosuccinimide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; dibenzoyl peroxide; In methanol; N,N-dimethyl-formamide; chlorobenzene; mineral oil;

DOI:10.1124/mol.113.091249

upstream raw materials:

3-chloro-1-(o-methoxyphenoxy)propylbenzene

methylamine

phenylpropyl chloride

1-bromo-3-chloro-1-phenylpropane

Refernces

Asymmetric hydrogenation of β-amino ketones with the bimetallic complex RuPHOX-Ru as the chiral catalyst

10.1039/c3ob40135a

The study focuses on the asymmetric hydrogenation of β-amino ketones using a bimetallic complex, RuPHOX-Ru, as a chiral catalyst. The primary aim was to develop an efficient, environmentally friendly, and cost-effective method for synthesizing enantiomerically pure γ-amino alcohols, which are key intermediates in the production of antidepressants such as fluoxetine, tomoxetine, and nisoxetine. The researchers utilized a mixed solvent system of toluene and water, with KOH as the base, under a hydrogen atmosphere to achieve high yields and enantioselectivities (up to 99.9% ee) for the hydrogenation reactions. The study demonstrates that the RuPHOX-Ru catalyst is stable, can be used with low catalyst loadings, and offers a promising alternative for the synthesis of these drugs and their analogues.

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