Citalopram

Base Information

• Chemical Name: Citalopram
• CAS No.: 59729-33-8
• Molecular Formula: C20H21FN2O
• Molecular Weight: 324.398
• European Community (EC) Number: 261-891-1
• UNII: 0DHU5B8D6V
• DSSTox Substance ID: DTXSID8022826
• Nikkaji Number: J18.081E
• Wikipedia: Citalopram
• Wikidata: Q409672
• NCI Thesaurus Code: C61680
• RXCUI: 2556
• Pharos Ligand ID: G1J69NL9LH2V
• Metabolomics Workbench ID: 144961
• ChEMBL ID: CHEMBL549
• Mol file: 59729-33-8.mol

Synonyms:Celexa;Citalopram;Citalopram Hydrobromide;Cytalopram;Lu-10-171;Lu10171;Seropram

Chemical Property of Citalopram

Chemical Property:

• Appearance/Colour: grease
• Melting Point: 182-183 °C
• Boiling Point: 428.3 °C at 760 mmHg
• PKA: pKa 9.38(H2O) (Uncertain)
• Flash Point: 212.8 °C
• PSA: 36.26000
• Density: 1.18 g/cm³
• LogP: 3.81298
• Storage Temp.: Store at RT
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 324.16379146
• Heavy Atom Count: 24
• Complexity: 466

Purity/Quality:

99% ^*data from raw suppliers

Citalopram, Hydrobromide Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
• Recent ClinicalTrials: Vortioxetine in the Elderly vs. Selective Serotonin Reuptake Inhibitors (SSRIs): a Pragmatic Assessment
• Recent EU Clinical Trials: Effect of citalopram on chest pain in patients with functional chest pain
• Description: Citalopram is a specific serotonin-uptake inhibitor useful in the treatment of depression. In endogenous depression citalopram was reported to be as effective as amitriptyline and mianserin, while being inferior to clomipramine in both endogenous and non-endogenous depression.
• Uses: scabicide antidepressant monoamine oxidase inhibitor (MAOIs)
• Biological Functions: Citalopram (Celexa) has an elimination half-life of 35 hours and is 80% bound to plasma proteins. Of all of the SSRIs it has the least effect on the cytochrome P450 system and has the most favorable profile regarding drug–drug interactions.
• Clinical Use: SSRI antidepressant: Depressive illness Panic disorder
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: increased risk of bleeding with aspirin and NSAIDs; risk of CNS toxicity increased with tramadol. Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone, disopyramide and dronedarone - avoid. Antibacterials: possibly increased risk of ventricular arrhythmias with IV erythromycin, moxifloxacin, pentamidine and telithromycin. Anticoagulants: effect of coumarins possibly enhanced; possibly increased risk of bleeding with dabigatran. Antidepressants: avoid with MAOIs and moclobemide, increased risk of toxicity; avoid with St John’s wort; possibly enhanced serotonergic effects with dapoxetine and duloxetine; can increase tricyclics antidepressant concentration; increased agitation and nausea with tryptophan; possible increased risk of convulsions with vortioxetine. Antiepileptics: convulsive threshold lowered. Antihistamines: increased risk of ventricular arrhythmias with mizolastine - avoid. Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol; possible increased risk of ventricular arrhythmias with chloroquine and quinine. Antipsychotics: possibly increased clozapine concentration; increased risk of ventricular arrhythmias with haloperidol and pimozide - avoid. Antivirals: concentration possibly increased by ritonavir. Beta-blockers: increased risk of ventricular arrhythmias with sotalol - avoid. Dopaminergics: avoid with selegiline; increased risk of CNS toxicity with rasagiline. 5 HT1 agonist: increased risk of CNS toxicity - avoid; possibly increased risk of serotonergic effects with naratriptan. Linezolid: use with care, possibly increased risk of side effects. Lithium: increased risk of CNS effects. Methylthioninium: risk of CNS toxicity - avoid if possible.

Technology Process of Citalopram

There total 65 articles about Citalopram 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%

citalopram hydrobromide (59729-32-7) → 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (59729-33-8)

Guidance literature:

With sodium hydroxide; In water;

Reference yield: 95.0%

3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (445312-08-3) + 3-(N,N-dimethylamino)propylmagnesium chloride (19070-16-7) → 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (59729-33-8)

Guidance literature:

With ammonium chloride; In tetrahydrofuran; water; toluene;

Reference yield: 93.0%

1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (64169-67-1) + 3-(Dimethylamino)propyl chloride (109-54-6) → 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (59729-33-8)

Guidance literature:

1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; 3-(Dimethylamino)propyl chloride; With sodium hydride; In 1,3-dimethyl-2-imidazolidinone; toluene; at 40 - 50 ℃; for 0.666667h;

With hydrogenchloride; water; at 65 - 70 ℃; for 3h;

With sodium hydroxide; In water; toluene; Product distribution / selectivity;

upstream raw materials:

citalopram hydrobromide

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

copper(I) cyanide

4,4-dimethyl-[2-[3-hydroxymethyl-4-[4-fluoro-a-hydroxy-a-(dimethylamino)propyl]benzyl]phenyl]oxazoline

Downstream raw materials:

citalopram hydrobromide

escitalopram

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

Refernces

• 1、 -. "Method for preparing citalopram and S - citalopram". Paragraph 0011; 0024-0025. . Retrieved 2021/07/01.
• 2、 Kristensen, Steffan K.,Eikeland, Espen Z.,Taarning, Esben,Lindhardt, Anders T.,Skrydstrup, Troels. "Ex situ generation of stoichiometric HCN and its application in the Pd-catalysed cyanation of aryl bromides: Evidence for a transmetallation step between two oxidative addition Pd-complexes". . p. 8094 - 8105. Retrieved 2017/11/27.