Citalopram hydrobromide CAS 59729-32-7
Introduction：Basic information about Citalopram hydrobromide CAS 59729-32-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Citalopram hydrobromide Basic informationAbstract Efficacy Side effects References
| Product Name: | Citalopram hydrobromide |
| Synonyms: | Citalopran HBr;1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile hydrobromi;Citalopram hydrobromide solution;Citalopram HBr Salt;1-[3-(DIMETHYLAMINO)PROPYL]-1-(4-FLUOROPHENYL)-1,3-DIHYDRO-5-ISOBENZOFURANCARBONITRILE HYDROBROMIDE;1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile hydrobr;CITALOPRAM HBR;(+/-)-CITALOPRAM HYDROBROMIDE |
| CAS: | 59729-32-7 |
| MF: | C20H22BrFN2O |
| MW: | 405.3 |
| EINECS: | 261-890-6 |
| Product Categories: | Pharmaceutical intermdiate;Other APIs;Heterocyclic Compounds;Serotonin;APIs;Neurochemicals,Pharmaceuticals;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals;Citalopram |
| Mol File: | 59729-32-7.mol |
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. |
| Major Application | clinical testing |
| InChI | 1S/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 |
| InChIKey | WIHMBLDNRMIGDW-UHFFFAOYSA-N |
| SMILES | Br.CN(C)CCCC1(OCc2cc(ccc12)C#N)c3ccc(F)cc3 |
| CAS DataBase Reference | 59729-32-7(CAS DataBase Reference) |
Safety Information
| Hazard Codes | F,T |
| Risk Statements | 11-23/24/25-39/23/24/25-22 |
| Safety Statements | 7-16-36/37-45-24/25 |
| RIDADR | 3249 |
| WGK Germany | 3 |
| RTECS | NP6313500 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29329990 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Flam. Liq. 2 STOT SE 1 |
| 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:
|
| 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 byordinary 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). Afteraddition, the mixture was left at room temperature for 16 hours. The volatilematerials were removed in vacuo and the residue was taken up in water (100mL). pH was adjusted to 5.5 by adding HCl (aqueous, 4 N). The aqueousphase was extracted with toluene (100 mL). The toluene was removed invacuo 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 (150mL) was added n-BuLi (1.6 M in hexanes, 40 mL) at -78 to -65°C. Thetemperature of the solution was allowed to raise to -30°C over a period of 2hours. 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 materialswere removed in vacuo and the residue was taken up in water (100 mL). pHwas adjusted to 5.5 by adding HCl (aqueous, 4 N). The aqueous phase wasextracted with toluene (100 mL). The toluene was removed in vacuo and the5-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 ofisopropylmagnesium chloride (8.0 mL, 2 M in diethyl ether) in THF (25 mL) at0°C. The resulting mixture was stirred at 0°C for 1 h, then cooled to -78°Cand 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. Themixture was allowed to warm to -10°C during 1 h, then cooled again to -78°Cand CO2 (5.7 g, 130 mmol) was added. The mixture was allowed to warm toroom temperature, and then evaporated. Ion exchange chromatography of theresidue (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 mixturewas raised to 130°C for 2 hours. The reaction mixture was allowed to cool to75°C and water (25 mL) was added. The temperature was held at 75°C for 15min, and then the reaction mixture was cooled to room temperature. pH wasajusted to 9 with ammonium hydroxide and then n-heptane (75 mL) wasadded. The temperature was raised to 70°C and the hot n-heptane layer wasisolated 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 fromisopropanol; 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] YOLANDA MATEO. Inhibition of 5-hydroxytryptamine reuptake by the antidepressant citalopram in the locus coeruleus modulates the rat brain noradrenergic transmission in vivo[J]. Neuropharmacology, 2000, 39 11: Pages 2036-2043. DOI:10.1016/s0028-3908(00)00041-1 [2] JOHN LEKAKIS . 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[J]. International journal of cardiology, 2010, 139 2: Pages 150-158. DOI:10.1016/j.ijcard.2008.10.010 [3] ANDREA CIPRIANI. Comparative efficacy and acceptability of 12 new-generation antidepressants: a multiple-treatments meta-analysis.[J]. Lancet (London, England), 2009, 373 9665: 746-758. DOI:10.1016/s0140-6736(09)60046-5 [4] CLAUDIO A NARANJO MD Edward M S M, PHD. The serotonin uptake inhibitor citalopram attenuates ethanol intake[J]. Clinical Pharmacology & Therapeutics, 1987, 41 3: 266-274. DOI:10.1038/clpt.1987.27 |
Citalopram hydrobromide Preparation Products And Raw materials
| Raw materials | n-Butyllithium-->Magnesium-->Thionyl chloride-->ISOPROPYLMAGNESIUM CHLORIDE-->Carbon dioxide-->tert-Butyl methyl ether-->Sulfamide-->Phthalan |
