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| | Citalopram hydrobromide Chemical Properties |
| Melting point | 182-188°C | | Fp | 9℃ | | storage temp. | 2-8°C | | solubility | H2O: soluble (sparingly) | | form | powder | | color | White | | Water Solubility | Soluble to 50 mM in ethanol and to 10 mM in water | | Merck | 14,2318 | | Stability: | Stable. Incompatible with strong oxidizing agents. | | CAS DataBase Reference | 59729-32-7(CAS DataBase Reference) |
| | Citalopram hydrobromide Usage And Synthesis |
| 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 | http://www.rxlist.com/celexa-drug.htm
https://en.wikipedia.org/wiki/Citalopram
https://www.drugs.com/citalopram.html | | 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 | An inhibitor of serotonin (5-HT) uptake. Used as an antidepressant | | Uses | Antidepressant;5HT uptake inhibitor | | Uses | Anti-depressant/Anti-psychotic | | Uses | 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
| | 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 |
| | Citalopram hydrobromide Preparation Products And Raw materials |
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