Norfluoxetine hydrochloride

Base Information

• Chemical Name: Norfluoxetine hydrochloride
• CAS No.: 57226-68-3
• Molecular Formula: C₁₆H₁₆F₃NO*ClH
• Molecular Weight: 331.765
• European Community (EC) Number: 809-411-7
• DSSTox Substance ID: DTXSID30972680
• Mol file: 57226-68-3.mol

Synonyms:desmethylfluoxetine;norfluoxetin;norfluoxetine;norfluoxetine hydrochloride;norfluoxetine, (+-)-isomer

Chemical Property of Norfluoxetine hydrochloride

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 5.21E-06mmHg at 25°C
• Boiling Point: 381.1 °C at 760 mmHg
• Flash Point: 184.3 °C
• PSA: 35.25000
• Density: 1.204g/cm³
• LogP: 5.67660
• Storage Temp.: -20°C
• Solubility.: H2O: >4 mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 331.0950763
• Heavy Atom Count: 22
• Complexity: 294

Purity/Quality:

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

Norfluoxetine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CCN)OC2=CC=C(C=C2)C(F)(F)F.Cl
• Description: Norfluoxetine is an active metabolite of the antidepressant fluoxetine. It is formed from fluoxetine by the cytochrome P450 (CYP) isoforms CYP2C9, CYP2C19, and CYP3A. Norfluoxetine inhibits serotonin (5-HT) uptake in rat brain synaptosomal membrane preparations (Ki = 44.7 nM) and isolated human platelets (IC50 = ~15 nM). It has been found in the tissues of fish exposed to wastewater effluent.
• Uses: Norfluoxetine Hydrochloride is a metabolite of Fluoxetine (F597100), a selective serotonin reuptake inhibitor which is used as an antidepressant. Norfluoxetine hydrochloride has been used to examine if psychoactive pharmaceuticals in drinking water at environmental concentrations could induce neuronal gene expression. It has also been used to examine whether at environmental concentrations it can alter in vitro expression of autism spectrum disorders (ASD)-associated synaptic proteins in human neurons.

Technology Process of Norfluoxetine hydrochloride

There total 4 articles about Norfluoxetine hydrochloride 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-hydroxy-3-phenylpropanenitrile (73627-97-1,121617-17-2,132203-26-0,17190-29-3) → (R)-norfluoxetine hydrochloride (138614-32-1,57226-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen, NH₃ / Raney Ni / ethanol / 90 °C / p(NH₃) = 30 psi and p(H₂) = 170 psi

2: 1) NaH / 1) DMSO, 50 deg C, 20 min, 2) DMSO, 90 deg C, 40 min

With ammonia; hydrogen; sodium hydride; nickel; In ethanol;

DOI:10.1016/S0040-4039(00)76212-5

Reference yield:

3-hydroxy-3-phenylpropanenitrile (73627-97-1,121617-17-2,132203-26-0,17190-29-3) → (S)-(+)-norfluoxetine hydrochloride (138614-32-1,57226-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen, NH₃ / Raney Ni / ethanol / 90 °C / p(NH₃) = 30 psi and p(H₂) = 170 psi

2: 1) NaH / 1) DMSO, 50 deg C, 20 min, 2) DMSO, 90 deg C, 40 min

With ammonia; hydrogen; sodium hydride; nickel; In ethanol;

DOI:10.1016/S0040-4039(00)76212-5

Reference yield:

4-chlorobenzotrifluoride (98-56-6) + (1R)-3-amino-1-phenyl-1-propanol (138750-31-9) → (R)-norfluoxetine hydrochloride (138614-32-1,57226-68-3)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1) DMSO, 50 deg C, 20 min, 2) DMSO, 90 deg C, 40 min;

DOI:10.1016/S0040-4039(00)76212-5

upstream raw materials:

4-chlorobenzotrifluoride

(1R)-3-amino-1-phenyl-1-propanol

3-hydroxy-3-phenylpropanenitrile

(1S)-3-amino-1-phenyl-1-propanol

Downstream raw materials:

(S)-fluoxetine

Refernces