Fluoxetine

Base Information

• Chemical Name: Fluoxetine
• CAS No.: 54910-89-3
• Deprecated CAS: 52341-67-0,57226-07-0,57226-07-0
• Molecular Formula: C₁₇H₁₈F₃NO
• Molecular Weight: 309.331
• Hs Code.: 29036990
• European Community (EC) Number: 611-209-7
• NSC Number: 283480
• UNII: 01K63SUP8D
• DSSTox Substance ID: DTXSID7023067
• Nikkaji Number: J292.434J
• Wikipedia: Fluoxetine
• Wikidata: Q422244
• NCI Thesaurus Code: C506
• RXCUI: 4493
• Pharos Ligand ID: MZYFV13ALAYR
• Metabolomics Workbench ID: 42819
• ChEMBL ID: CHEMBL41
• Mol file: 54910-89-3.mol

Synonyms:Fluoxetin;Fluoxetine;Fluoxetine Hydrochloride;Lilly 110140;Lilly-110140;Lilly110140;N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine;Prozac;Sarafem

Chemical Property of Fluoxetine

Chemical Property:

• Melting Point: 158oC
• Boiling Point: 395.1 °C at 760 mmHg
• PKA: 10.05±0.10(Predicted)
• Flash Point: 192.8 °C
• PSA: 21.26000
• Density: 1.159 g/cm³
• LogP: 4.82590
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 309.13404868
• Heavy Atom Count: 22
• Complexity: 308

Purity/Quality:

99% ^*data from raw suppliers

Fluoxetine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CNCCC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F
• Recent ClinicalTrials: Clinical Trial of Fluoxetine in Anxiety and Depression in Children, and Associated Brain Changes
• Recent EU Clinical Trials: PARACHUTES: Pedophilia At Risk – Acute Treatment – E-therapy vs SSRI
• Recent NIPH Clinical Trials: Study of the role of micro RNAs 16 and 135a in patients with lifelong premature ejaculation: A prospective case control study
• General Description: Fluoxetine, also known by trade names such as Prozac, is a selective serotonin reuptake inhibitor (SSRI) commonly prescribed for the treatment of major depressive disorder, obsessive-compulsive disorder, panic disorder, and bulimia nervosa. It works by increasing serotonin levels in the brain, which helps regulate mood, emotion, and behavior. Fluoxetine is characterized by its long half-life and active metabolite, norfluoxetine, contributing to its sustained therapeutic effects. While generally well-tolerated, it may cause side effects such as nausea, insomnia, and sexual dysfunction. Its efficacy and safety profile have made it a widely used antidepressant since its approval.

Technology Process of Fluoxetine

There total 129 articles about Fluoxetine 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%

2,2,2-trifluoro-N-methyl-N-(3-phenyl-3-(4-(trifluoromethyl)phenoxy)propyl)acetamide → FLUOXETINE (54910-89-3,57226-07-0,100568-02-3,100568-03-4,59333-67-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1039/c9ob02635e

Reference yield: 87.0%

3-methylamino-1-phenylpropan-1-ol (42142-52-9) + 4-chlorobenzotrifluoride (98-56-6) → FLUOXETINE (54910-89-3,57226-07-0,100568-02-3,100568-03-4,59333-67-4)

Guidance literature:

3-methylamino-1-phenylpropan-1-ol; With sodium hydride; In dimethyl sulfoxide; at 60 ℃; for 1h; Inert atmosphere;

4-chlorobenzotrifluoride; In dimethyl sulfoxide; at 100 ℃; for 10h; Inert atmosphere;

With water; In diethyl ether; dimethyl sulfoxide;

DOI:10.1080/00397910903422518

Reference yield: 86.0%

3-methylamino-1-phenylpropan-1-ol (42142-52-9) + 4-hydroxybenzotrifluoride (402-45-9) → FLUOXETINE (54910-89-3,57226-07-0,100568-02-3,100568-03-4,59333-67-4)

Guidance literature:

With tributylphosphine; di-isopropyl azodicarboxylate; In dichloromethane; N,N-dimethyl acetamide; at 70 ℃; for 0.0833333h;

DOI:10.1039/c0ob00906g

upstream raw materials:

N-benzyl-N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropyl-amine

3-(benzyl-methyl-amino)-1-phenylpropan-1-one

acetophenone

3-(N-benzyl-N-methylamino)-1-phenyl-propan-1-ol

Downstream raw materials:

(R)-fluoxetine

(S)-fluoxetine

N-methyl-N-(3-phenyl-3-(4-(trifluoromethyl)phenoxy)propyl)formamide

N-(2-Oxycarbonylethyl)fluoxetin

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.