R-DESMETHYLCITALOPRAM

Base Information

• Chemical Name: R-DESMETHYLCITALOPRAM
• CAS No.: 144010-85-5
• Molecular Formula: C₁₉H₁₉FN₂O
• Molecular Weight: 310.371
• Mol file: 144010-85-5.mol

Synonyms:5-Isobenzofurancarbonitrile,1-(4-fluorophenyl)-1,3-dihydro-1-[3-(methylamino)propyl]-, (R)-;(R)-(-)-N-Demethylcitalopram; (R)-Desmethylcitalopram

Chemical Property of R-DESMETHYLCITALOPRAM

Chemical Property:

• Melting Point: 70-72°C
• PSA: 45.05000
• LogP: 3.86168
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-DesmethylCitalopramHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The (R)-enantiomer metabolite of Citalopram, an inhibitor of serotonin (5-HT) uptake. Used as an antidepressant. The (R)-enantiomer metabolite of Citalopram, an inhibitor of serotonin (5-HT) uptake. (R)-Desmethyl Citalopram hydrochloride is used as an antidepressant

Technology Process of R-DESMETHYLCITALOPRAM

There total 34 articles about R-DESMETHYLCITALOPRAM 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%

escitalopram oxalate (219861-08-2) → (+)-Desmethylcitalopram (144025-14-9,144010-85-5)

Guidance literature:

escitalopram oxalate; With ammonium hydroxide; In ethyl acetate; for 0.5h;

With carbonochloridic acid 1-chloro-ethyl ester; In toluene; at 110 ℃; for 6h;

DOI:10.1016/j.bmc.2015.01.047

Reference yield: 91.5%

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)

Guidance literature:

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile; With carbonochloridic acid 1-chloro-ethyl ester; In dichloromethane; toluene; at 10 - 20 ℃; Industry scale;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; at 20 - 65 ℃; Industry scale;

Reference yield: 78.0%

citalopram hydrobromide (59729-32-7) → rac-desmethylcitalopram (62498-67-3,144010-85-5)

Guidance literature:

citalopram hydrobromide; With ammonium hydroxide; In water;

With carbonochloridic acid 1-chloro-ethyl ester; In 1,2-dichloro-ethane; at 0 ℃; for 18h; Inert atmosphere; Reflux;

DOI:10.1021/ml5000806

upstream raw materials:

{3-[5-cyano-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-1-yl]-propyl}-methyl-carbamic acid 1-chloro-ethyl ester

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

3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine

copper(I) cyanide

Downstream raw materials:

(-)-Didemethylcitalopram

(+)-Didemethylcitalopram

(S)-(3-(5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)propyl)dimethylselenonium trifluoromethanesulfonate

(S)-1-(4-fluorophenyl)-1-(3-(methylthio)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile

Refernces

• 1、 Hu, Xiao-Xia,Yuan, Ling-Jing,Fang, Ping,Mao, Yong-Hui,Zhan, Yun-Yun,Li, Xiang-Yu,Dai, Da-Peng,Cai, Jian-Ping,Hu, Guo-Xin. "Effect of CYP2D6 genetic polymorphism on the metabolism of citalopram in vitro". . p. 133 - 138. Retrieved 2016.
• 2、 -. "Antiprotozoal amidine compounds". Page/Page column 14. . Retrieved 2015/11/09.