Citalopram hydrobromide

Description

Citalopram (hydrobromide) (Item No. 23252) is an analytical reference material categorized as an antidepressant. This product is intended for use in analytical forensic applications. This product is also available as a general research tool .

Chemical properties

White or almost white, crystalline powder.

Originator

Celexa,Lundbeck, Forest

The Uses of Citalopram hydrobromide

Citalopram hydrobromide has been used:

• to examine its effects on?sirt?mRNA and mammalian sirtuins (SIRT) expression in mice
• to monitor body temperature and antidepressant-like behavioral responses in the forced swim test for rats
• for 5-hydroxytryptamine (5-HT) competition uptake assays

The Uses of Citalopram hydrobromide

An inhibitor of serotonin (5-HT) uptake. Used as an antidepressant

The Uses of Citalopram hydrobromide

Antidepressant;5HT uptake inhibitor

The Uses of Citalopram hydrobromide

Anti-depressant/Anti-psychotic

What are the applications of Application

Citalopram, Hydrobromide Salt is a selective inhibitor of the 5-hydroxytryptamine transporter

Manufacturing Process

5-Carboxy-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3- dihydroisobenzofuranwas synthesized by three methods: 1. A solution of 1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3-dihydroisobenzofuran-5-yl magnesium bromide in dry THF (90 mL) (prepared by ordinary methods from 5-bromo-1-(4-fluorophenyl)-1-(3-
dimethylaminopropyl)-1,3-dihydro-isobenzofuran (9 g, 0.024 mole) and
magnesium (0.73 g, 0.03 mole)) was added to dry solid CO2 (50 g). After addition, the mixture was left at room temperature for 16 hours. The volatile materials were removed in vacuo and the residue was taken up in water (100 mL). pH was adjusted to 5.5 by adding HCl (aqueous, 4 N). The aqueous phase was extracted with toluene (100 mL). The toluene was removed in vacuo and the 5-carboxy-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3- dihydroisobenzofuran was obtained as oil. Yield 6 g.
2. To a solution of 5-bromo-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)- 1,3-dihydroisobenzofuran (9 g, 0.024 mole) in tertbutyl methyl ether (150 mL) was added n-BuLi (1.6 M in hexanes, 40 mL) at -78 to -65°C. The temperature of the solution was allowed to raise to -30°C over a period of 2 hours. The reaction mixture was added to dry solid CO2 (50 g). After addition, the mixture was left at room temperature for 16 hours. The volatile materials were removed in vacuo and the residue was taken up in water (100 mL). pH was adjusted to 5.5 by adding HCl (aqueous, 4 N). The aqueous phase was extracted with toluene (100 mL). The toluene was removed in vacuo and the 5-carboxy-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3- dihydroisobenzofuran was obtained as an oil. Yield 7.5 g.
3. n-BuLi (20 mL, 1.6 M in hexane) was added to a solution of isopropylmagnesium chloride (8.0 mL, 2 M in diethyl ether) in THF (25 mL) at 0°C. The resulting mixture was stirred at 0°C for 1 h, then cooled to -78°C and a solution of 5-bromo-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3- dihydro-isobenzofuran (5.0 g, 13.0 mmol) in THF (25 mL) was added. The mixture was allowed to warm to -10°C during 1 h, then cooled again to -78°C and CO2 (5.7 g, 130 mmol) was added. The mixture was allowed to warm to room temperature, and then evaporated. Ion exchange chromatography of the residue (Dowex RTM-50, acidic form) eluting with 1 M NH3 afforded the 5- carboxy-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3- dihydroisobenzofuran as a thick oil.
5-Carboxy-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3- dihydroisobenzofuran (5 g, 0.015 mole) and sulfamide (1.65 g, 0.017 mole) were dissolved in sulfolane (15 mL). Thionyl chloride (2.25 g, 0.019 mole) was added at room temperature and the temperature of the reaction mixture was raised to 130°C for 2 hours. The reaction mixture was allowed to cool to 75°C and water (25 mL) was added. The temperature was held at 75°C for 15 min, and then the reaction mixture was cooled to room temperature. pH was ajusted to 9 with ammonium hydroxide and then n-heptane (75 mL) was added. The temperature was raised to 70°C and the hot n-heptane layer was isolated from which the 5-cyano-1-(4-fluorophenyl)-1-(3- dimethylaminopropyl)-1,3-dihydroisobenzofuran (Citalopram, free base) crystallised on cooling. Yield 3.77 g. Purity (HPLC peak area) >97%. The hydrobromide was prepared in conventional manner and crystallized from isopropanol; melting point 148-150°C.

brand name

Celexa (Forest).

Therapeutic Function

Antidepressant

General Description

Citalopram is an antidepressant sold under the trade names Celexa^? and Cipramil for the treatment of major depression. Citalopram is a selective serotonin reuptake inhibitor, a class of drugs that also includes fluoxetine, paroxetine, and sertraline. This Certified Snap-N-Spike^? Solution is suitable for use in LC/MS or GC/MS applications for clinical toxicology, forensic analysis, urine drug testing, or pharmaceutical research.

Hazard

A poison.

Biochem/physiol Actions

Potent and selective serotonin uptake inhibitor (Ki = 5.4 nM); antidepressant

storage

Room temperature

References

1) Mateo?et al.?(2000),?Inhibition of 5-hydroxytryptamine reuptake by the antidepressant citalopram in the locus coeruleus modulates the rat brain noradrenergic transmission in vivo;?Neuropharmacology?39?2036 2) Lekakis?et al.?(2010),?Selective serotonin re-uptake inhibitors decrease the cytokine-induced endothelial adhesion molecule expression, the endothelial adhesiveness to monocytes and the circulating levels of vascular adhesion molecules; Int. J. Cardiol.?139?150 3) Cipriani?et al.?(2009),?Comparative efficacy and acceptability of 12 new-generation antidepressants: a multiple-treatments meta-analysis; Lancet?373?746 4) Naranjo?et al.?(1987),?The serotonin uptake inhibitor citalopram attenuates ethanol intake; Clin. Pharmacol. Ther.?41?266