Sertraline

Base Information

• Chemical Name: Sertraline
• CAS No.: 79617-95-1
• Molecular Formula: C17H17 Cl2 N
• Molecular Weight: 306.235
• European Community (EC) Number: 616-708-3,642-001-4
• UNII: QUC7NX6WMB
• DSSTox Substance ID: DTXSID6023577
• Nikkaji Number: J33.072H
• Wikipedia: Sertraline
• Wikidata: Q407617
• NCI Thesaurus Code: C61939
• RXCUI: 36437
• Pharos Ligand ID: YUTBHTLKAWT2
• Metabolomics Workbench ID: 38699
• ChEMBL ID: CHEMBL809
• Mol file: 79617-95-1.mol

Synonyms:Altruline;Apo Sertraline;Apo-Sertraline;Aremis;Besitran;Gen Sertraline;Gen-Sertraline;Gladem;Hydrochloride, Sertraline;Lustral;Novo Sertraline;Novo-Sertraline;ratio Sertraline;ratio-Sertraline;Rhoxal sertraline;Rhoxal-sertraline;Sealdin;Sertraline;Sertraline Hydrochloride;Sertraline Hydrochloride (1S-cis)-Isomer;Zoloft

Chemical Property of Sertraline

Chemical Property:

• Melting Point: 270-273?C
• PSA: 12.03000
• LogP: 5.57050
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 305.0738049
• Heavy Atom Count: 20
• Complexity: 322

Purity/Quality:

98%Min ^*data from raw suppliers

rac-cis-Sertraline Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CNC1CCC(C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl
• Isomeric SMILES: CN[C@H]1CC[C@H](C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl
• Recent ClinicalTrials: Vortioxetine in the Elderly vs. Selective Serotonin Reuptake Inhibitors (SSRIs): a Pragmatic Assessment
• Recent EU Clinical Trials: Antidepressant for the prevention of DEPression following first episode Psychosis trial
• Recent NIPH Clinical Trials: The psychotropic drug dopamine PET study
• Uses: Potent and selective inhibitors of serotonin uptake cis-Sertraline is an isomer of Sertraline. Sertraline is a selective serotonin reuptake inhibitor. It is used as an antidepressant.

Technology Process of Sertraline

There total 35 articles about Sertraline 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: 96.0%

[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]carbamic acid methyl ester → cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine (79617-95-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 70 ℃; for 1h;

DOI:10.1021/jo010370l

Reference yield: 95.0%

C19H18Cl5NO3S → cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine (79617-95-1)

Guidance literature:

With acetic acid; In methanol; for 48h; Inert atmosphere;

Reference yield: 80.0%

cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine hydrochloride (79617-89-3) → cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine (79617-95-1)

Guidance literature:

With sodium hydroxide; In water; ethyl acetate;

DOI:10.1021/cg901197b

upstream raw materials:

N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

(2E,4E)-5-(3,4-Dichloro-phenyl)-penta-2,4-dienoic acid

(2E,4E)-5-(3,4-Dichloro-phenyl)-penta-2,4-dienoic acid ethyl ester

(2E,4E)-5-(3,4-Dichloro-phenyl)-penta-2,4-dienoic acid benzyl ester

Downstream raw materials:

(cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate

Sertraline

(1R,4R)-sertraline

Refernces

• 1、 Kwan, Maria H.T.,Pokar, Nisha P.B.,Good, Catherine,Jones, Martin F.,Munday, Rachel,Screen, Thomas,Blacker, A. John. "Deactivation mechanisms of iodo-iridium catalysts in chiral amine racemization". supporting information. . Retrieved 2020/12/29.
• 2、 Tang, Conghui,Okumura, Mikiko,Zhu, Yunbo,Hooper, Annie R.,Zhou, Yu,Lee, Yu-Hsuan,Sarlah, David. "Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents". . p. 10245 - 10249. Retrieved 2019/07/04.