Citalopram N-oxide

Base Information

• Chemical Name: Citalopram N-oxide
• CAS No.: 63284-72-0
• Molecular Formula: C20H21 F N2 O2
• Molecular Weight: 340.397
• European Community (EC) Number: 810-750-8
• UNII: 9E2C7VT4RR
• DSSTox Substance ID: DTXSID50435141
• Nikkaji Number: J378.717F
• Wikidata: Q27149646
• ChEMBL ID: CHEMBL3544717
• Mol file: 63284-72-0.mol

Synonyms:Citalopram N-oxide;63284-72-0;9E2C7VT4RR;Citalopram-d6N-Oxide;UNII-9E2C7VT4RR;3-[5-cyano-1-(4-fluorophenyl)-3H-2-benzofuran-1-yl]-N,N-dimethylpropan-1-amine oxide;LU-11-305;CHEBI:80602;1-(3-(Dimethyloxidoamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile;5-Isobenzofurancarbonitrile, 1-(3-(dimethyloxidoamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-;Citalopram USP RC E;CHEMBL3544717;DTXSID50435141;AKOS030255385;FT-0665068;FT-0665070;FT-0665071;FT-0665072;Q27149646;3-(5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine oxide

Chemical Property of Citalopram N-oxide

Chemical Property:

• Melting Point: 91-93°C
• PKA: 4.73±0.40(Predicted)
• PSA: 62.45000
• LogP: 3.84648
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 340.15870608
• Heavy Atom Count: 25
• Complexity: 509

Purity/Quality:

99%, ^*data from raw suppliers

Citalopram N-oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+](C)(CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F)[O-]
• Uses: Citalopram N-Oxide (Escitalopram EP Impurity H; Citalopram USP Related Compound E) is a metabolite of Citalopram (CT). A metabolite of Citalopram (CT)

Technology Process of Citalopram N-oxide

There total 2 articles about Citalopram N-oxide 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:

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (59729-33-8) → rac-desmethylcitalopram (62498-67-3,144010-85-5) + Citalopram N-Oxide (63284-72-0,917482-45-2)

Guidance literature:

With NADH; In methanol; at 37 ℃; for 0.5h; pH=7.4; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1016/j.dmpk.2016.01.001

Reference yield:

citalopram hydrobromide (59729-32-7) → 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide (64372-56-1) + Citalopram N-Oxide (63284-72-0,917482-45-2) + 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-3hydroxy-1,3-dihydroisobenzofuran-5-carboxylic acid amide (1347761-10-7)

Guidance literature:

With water; sodium hydroxide; for 384h; Photolysis;

DOI:10.1590/S0103-50532011000500005

upstream raw materials:

citalopram hydrobromide

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile