N-Desmethylvenlafaxine

Base Information

• Chemical Name: N-Desmethylvenlafaxine
• CAS No.: 149289-30-5
• Molecular Formula: C16H25 N O2
• Molecular Weight: 263.38
• UNII: 19V5EX4E8B
• DSSTox Substance ID: DTXSID20881050
• Nikkaji Number: J347.734G
• Wikidata: Q27156915
• Metabolomics Workbench ID: 42516
• ChEMBL ID: CHEMBL1119
• Mol file: 149289-30-5.mol

Synonyms:N-desmethyl venlafaxine;N-desmethylvenlafaxine

Chemical Property of N-Desmethylvenlafaxine

Chemical Property:

• Vapor Pressure: 5.49E-07mmHg at 25°C
• Melting Point: 61-63°C
• Refractive Index: 1.543
• Boiling Point: 396.2°C at 760 mmHg
• PKA: 14.83±0.20(Predicted)
• Flash Point: 193.4°C
• PSA: 41.49000
• Density: 1.067g/cm³
• LogP: 3.08430
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 263.188529040
• Heavy Atom Count: 19
• Complexity: 256

Purity/Quality:

97% ^*data from raw suppliers

racN-DesmethylVenlafaxine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCC(C1=CC=C(C=C1)OC)C2(CCCCC2)O
• Uses: D,L N-Desmethylvenlafaxine is a metabolite of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant A metabolite of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant.

Technology Process of N-Desmethylvenlafaxine

There total 7 articles about N-Desmethylvenlafaxine 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: 88.8%

N-[2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide (272788-07-5) → N-Desmethylvenlafaxine (149289-30-5)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 5h; Reflux;

Reference yield:

methylamine hydrochloride (593-51-1) + 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol (93413-76-4,131801-69-9) → N-Desmethylvenlafaxine (149289-30-5)

Guidance literature:

With hydrogen; Pd-alumina; In methanol; at 20 ℃; for 24h; under 760.051 - 1520.1 Torr;

Reference yield:

p-methoxybenzylnitrile (104-47-2) → N-Desmethylvenlafaxine (149289-30-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi / 1.) THF, hexane, -70 deg C, 30 min, 2.) -65 deg C, 2 h

2: H₂ / 5percent Rh/Al₂O₃ / ethanol; aq. NH₃

3: 1.) NaHCO₃, 2.) LiAlH₄ / 1.) CH₂Cl₂, RT, 20 h, 2.) THF, reflux, 1.5 h

With lithium aluminium tetrahydride; n-butyllithium; hydrogen; sodium hydrogencarbonate; Rh/Al₂O₃; In ammonium hydroxide; ethanol;

DOI:10.1021/jm00172a035

upstream raw materials:

chloroformic acid ethyl ester

N,N-didesmethylvenlafaxine

cyclohexanone

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol

Downstream raw materials:

N-Desmethylvenlafaxine hydrochloride

N-Desmethyldesvenlafaxine