Cidoxepin

Base Information

• Chemical Name: Cidoxepin
• CAS No.: 3607-18-9
• Molecular Formula: C₁₉H₂₁NO
• Molecular Weight: 279.382
• UNII: F96TTB8728
• DSSTox Substance ID: DTXSID301318253
• Nikkaji Number: J9.508G,J8.179E
• Wikipedia: Cidoxepin,Doxepin
• Wikidata: Q416791
• NCI Thesaurus Code: C65328
• RXCUI: 3638
• Pharos Ligand ID: VP48GX1L54L3
• Metabolomics Workbench ID: 43364
• ChEMBL ID: CHEMBL101740
• Mol file: 3607-18-9.mol

Synonyms:Apo Doxepin;Apo-Doxepin;ApoDoxepin;Aponal;Deptran;Desidox;Doneurin;Doxepia;Doxepin;Doxepin beta;Doxepin Hydrochloride;Doxepin Hydrochloride, Cis-Trans Isomer Mixture (approximately 1:5);Doxepin RPh;Doxepin-RPh;Espadox;Hydrochloride, Doxepin;Mareen;Novo Doxepin;Novo-Doxepin;Prudoxin;Quitaxon;Sinequan;Sinquan;Xepin;Zonalon

Chemical Property of Cidoxepin

Chemical Property:

• Vapor Pressure: 4.87E-07mmHg at 25°C
• Melting Point: 192-193°
• Refractive Index: 1.629
• Boiling Point: 413.3°C at 760 mmHg
• Flash Point: 121.3°C
• PSA: 12.47000
• Density: 1.122g/cm³
• LogP: 3.96240
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 279.162314293
• Heavy Atom Count: 21
• Complexity: 363

Purity/Quality:

90%+ ^*data from raw suppliers

DOXEPIN HYDROCHLORIDE IMPURITY-D 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CN(C)CCC=C1C2=CC=CC=C2COC3=CC=CC=C31
• Isomeric SMILES: CN(C)CC/C=C\1/C2=CC=CC=C2COC3=CC=CC=C31
• Recent ClinicalTrials: Characterization of New Human Models of Non-histaminergic Itch and Their Interaction With the TRPM8 Receptor
• Recent EU Clinical Trials: Pharmacovigilance in children and adolescents:
• Uses: Antidepressant.

Technology Process of Cidoxepin

There total 31 articles about Cidoxepin 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: 93.0%

doxepin N-oxide (22684-91-9) → doxepin (1668-19-5,3607-18-9,3607-34-9)

Guidance literature:

With sodium tetrahydroborate; In water; at 50 - 60 ℃; chemoselective reaction;

DOI:10.1016/j.tetlet.2010.08.045

Reference yield: 76.57%

6,11-dihydrodibenz[b,e]oxepin-11-one (4504-87-4) + diethyl 3-(N,N-dimethylamino)propylphosphonate (79333-82-7) → doxepin (1668-19-5,3607-18-9,3607-34-9)

Guidance literature:

diethyl 3-(N,N-dimethylamino)propylphosphonate; With sodium hydride; In tetrahydrofuran; at -40 ℃; for 0.5h; Inert atmosphere;

6,11-dihydrodibenz[b,e]oxepin-11-one; In tetrahydrofuran; at -40 ℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield: 74.52%

6,11-dihydrodibenz[b,e]oxepin-11-one (4504-87-4) + chlorure de N,N-dimethylamino-3 propyltriphenylphosphonium (83300-00-9) → doxepin (1668-19-5,3607-18-9,3607-34-9)

Guidance literature:

chlorure de N,N-dimethylamino-3 propyltriphenylphosphonium; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

6,11-dihydrodibenz[b,e]oxepin-11-one; In tetrahydrofuran; at 0 ℃; for 18h; Temperature; Reagent/catalyst; Inert atmosphere;

upstream raw materials:

doxepin hydrochloride

dimethyl amine

11-(3-chloropropylidene)-6,11-dihydrodibenzo-[b,e]-oxepine

doxepin N-oxide

Downstream raw materials:

((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-{3-[6H-dibenzo[b,e]oxepin-(11E)-ylidene]-propyl}-dimethyl-ammonium; chloride

((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-{3-[6H-dibenzo[b,e]oxepin-(11E)-ylidene]-propyl}-dimethyl-ammonium; chloride

doxepin N-oxide

Doxepin hydrochloride

Refernces

• 1、 -. "Synthesis method of doxepin hydrochloride". . . Retrieved 2021/11/03.
• 2、 -. "Synthetic method of doxepin hydrochloride". . . Retrieved 2020/12/30.