59729-32-7 Usage
Abstract
Citalopram hydrobromide (citalopram HBr) is an orally administered selective serotonin reuptake inhibitor (SSRI) with a chemical structure unrelated to that of other SSRIs or of tricyclic, tetracyclic, or other available antidepressant agents.
Citalopram HBr occurs as a fine, white to off-white powder. Citalopram HBr is sparingly soluble in water and soluble in ethanol.
The tablet is available as the brand-name drug Celexa. In Australia, the UK, Germany, Portugal, Poland, and most European countries, it is licensed for depressive episodes and panic disorder with or without agoraphobia. In Spain, it is also used for obsessive-compulsive disorder.
Efficacy
The advantage of this drug is that it has no effect on cholinergic muscarinic receptors, histamine receptors and α-adrenergic receptors . Because if these receptors are inhibited,? a lot of side effects caused by antidepressants will produce, such as dry mouth, sedation, orthostatic hypotension. Citalopram hydrobromide is effective for not only endogenous depression patients but also non-endogenous depression patients. Its antidepressant effect is usually established after 2-4 weeks . Citalopram hydrobromide does not affect the cardiac conduction system and blood pressure, which is particularly important for elderly patients. In addition, citalopram hydrobromide does not affect the blood, liver and kidney systems. Rare side effects and the most mild sedative properties make it particularly suitable for long-term treatment.It does not lead to weight gaining,and it does not strengthen the role of alcohol.
Side effects
You should not use this medicine if you are allergic to citalopram or escitalopram (Lexapro), or if you also take pimozide.
Do not use citalopram if you have used an monoamine oxidase inhibitor (MAOI) in the past 14 days. A dangerous drug interaction could occur. MAOI inhibitors include isocarboxazid, linezolid, methylene blue injection, phenelzine, rasagiline, selegiline, tranylcypromine, and others.
Side effects are usually small, very mild and transient. The most common adverse reactions are: nausea, increased sweating, salivation reduction, headaches and sleep time shortening. They are usually more obvious in the first or second week when treatment begins, and they generally disappear with the improvement of depression. In rare cases ,seizures have been observed. For? patients who suffer bradycardia , bradycardia can make treatment more complicated.
References
Different sources of media describe the References of 59729-32-7 differently. You can refer to the following data:
1. http://www.rxlist.com/celexa-drug.htm
https://en.wikipedia.org/wiki/Citalopram
https://www.drugs.com/citalopram.html
2. 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
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
Uses
Different sources of media describe the Uses of 59729-32-7 differently. You can refer to the following data:
1. An inhibitor of serotonin (5-HT) uptake. Used as an antidepressant
2. Antidepressant;5HT uptake inhibitor
3. Anti-depressant/Anti-psychotic
4. Citalopram hydrobromide has been used:to examine its effects on?sirt?mRNA and mammalian sirtuins (SIRT) expression in miceto monitor body temperature and antidepressant-like behavioral responses in the forced swim test for ratsfor 5-hydroxytryptamine (5-HT) competition uptake assays
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
Check Digit Verification of cas no
The CAS Registry Mumber 59729-32-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,7,2 and 9 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 59729-32:
(7*5)+(6*9)+(5*7)+(4*2)+(3*9)+(2*3)+(1*2)=167
167 % 10 = 7
So 59729-32-7 is a valid CAS Registry Number.
InChI:InChI=1/C20H21FN2O.BrH/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20;/h4-9,12H,3,10-11,14H2,1-2H3;1H
59729-32-7Relevant articles and documents
A New method for the production of citalopram and escitalopram using carbonates
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Paragraph 0052-0056, (2020/06/02)
In production of citalopram and escitalopram, the present invention relates to methods for producing citalopram and escitalopram of high purity and high yield and producing addition salt using the same which do not separately separate and obtain an intermediate compound before a cyclization reaction and conduct a cyclization reaction of 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile, represented by chemical formula 3, or (S)-(-)-4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)-benzonitrile, represented by chemical formula 3a, with a carbonate compound without a post treatment process such as separation, concentration, etc. of the intermediate compound.COPYRIGHT KIPO 2020
Preparation of Escitalopram, Its Salts and Intermediates
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, (2011/05/03)
The present patent application relates to an improved process for the preparation of escitalopram, its salts and intermediates. It also relates to a novel crystalline form S of citalopram diol intermediate, process for preparation and its use in the preparation of citalopram, escitalopram and their salts.
PREPARATION OF CITALOPRAM AND SALTS THEREOF
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Page/Page column 4, (2010/04/30)
Process for the preparation of citalopram and its salts, comprising reacting magnesium (5-cyano-2-(4-fluorobenzoyl)phenyl)methanolate bromide with 3-N,N-dimethylaminopropyl magnesium halide in a mixture of solvents, obtaining a diol intermediate in the form of its acid addition salt, and reacting the acid addition salt with sulfuric acid in an aqueous medium.
