Citalopram
citalopram
CAS: 59729-33-8
Molecular Formula: C20H21FN2O
Citalopram - Names and Identifiers
Citalopram - Physico-chemical Properties
| Molecular Formula | C20H21FN2O |
| Molar Mass | 324.39 |
| Density | 1.18±0.1 g/cm3(Predicted) |
| Melting Point | 156-157 °C |
| Boling Point | bp0.03 175-181° |
| Solubility | Methanol (Slightly), Water (Slightly) |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | pKa 9.38(H2O) (Uncertain) |
| Storage Condition | Sealed in dry,2-8°C |
| Physical and Chemical Properties | Oil, boiling point 175~181 C/4.00. Citalopram hydrobromide: C20H21FN2O? HBr. [59729-32-7]. Crystallization from isopropanol, melting point 182-183 °c. Citalopram Oxalate: C20H21FN2O? C2H2O4. Crystallization, melting point 164~166 deg C. |
Citalopram - Risk and Safety
| UN IDs | 3249 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
Citalopram - Nature
Open Data Verified Data
Oil, 175-181 °c.
Last Update：2024-01-02 23:10:35
Citalopram - Preparation Method
Open Data Verified Data
sodium hydride (dissolved in mineral oil) was dissolved in dimethyl sulfoxide with ammonia gas to obtain a sodium sulfinyl methyl solution. Cooling, Dropwise into 1-(4 fluorophenyl) a 1.3 dihydro-s-isobenzofuran nitrile dimethyl sulfoxide solution, reaction time. A solution of 3-= methylaminopropyl chloride in dimethyl sulfoxide was added. The reaction mixture was put into ice water and extracted with ether. The ether extract was then extracted with aqueous acetic acid. The aqueous acetic acid extract was basified with sodium hydroxide and then extracted with ether. The ethyl ether extract was washed with water, dried, active decolorization, vacuum concentration and distillation to obtain citalopram.
Last Update：2025-06-10 22:55:16
Citalopram - Application
Open Data Verified Data
developed by Lundbeck, Switzerland, launched in 1989. Xiamen Michael Pharmaceutical Co., Ltd. The second generation of antidepressants, serotonin reabsorption inhibition has a strong and specific inhibitory effect. For anti-depression, senile dementia and multi-infarct dementia.
Last Update：2025-08-19 16:24:40
Citalopram - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| Overview | Citalopram is one of the selective serotonin recovery inhibitors. Now depression is a common psychiatric mental illness, and most patients with Anxiety symptoms, this depression and Anxiety of the co-morbid phenomenon is not only common in young patients, and in elderly patients is more common, and even become one of the main symptoms of patients with medical treatment. Citalopram in the treatment of depression accompanied by Anxiety symptoms in elderly patients with depression, achieved good curative effect, with its mild effect, less drug interaction, however, it has little effect on the action of other neurotransmitters, especially cholinergic muscarinic receptors, histamine receptors and α-adrenergic receptors. Especially suitable for the elderly population. This product is the first serotonin reuptake inhibitor approved for clinical use in Denmark. It was successfully marketed in the United States in 1998. |
| pharmacological action | This product is a bicyclic hydrogenated phthalein derivative, selective serotonin (5-HT) reuptake inhibitor. The antidepressant effect is related to the inhibition of the reuptake of 5-HT by central nervous system neurons, thereby enhancing the function of central serotonergic nerves. This product is a highly selective 5-HT reuptake inhibitor, and has little effect on the reuptake of norepinephrine and dopamine. This product has no affinity for 5-HT1A, 5-HT2A, D1 receptor, D2 receptor, α1 receptor, α2 receptor, β receptor, H1 receptor, GABA receptor, M receptor, benzodiazepine receptor, or have only a lower affinity. In particular, it has no inhibitory effect on cholinergic muscarinic receptors, histamine receptors and α-adrenergic receptors. |
| synthesis | with 4-nitrophthalimide as the starting material, under alkaline conditions, the intermediate 5-amino phthalide was first synthesized by reduction with zinc powder, and the amino group was substituted with NaI to generate 5-iodine phthalide, and then with P-fluorophenyl magnesium bromide and 3, 3-dimethylpropylmagnesium chloride was subjected to two Grignard reactions, ring closure and finally cyanation to give citalopram. Figure 1 is the synthesis of citalopram |
| pharmacokinetics | This product is an oral drug with an oral bioavailability of approximately 80%. Maximum plasma levels of citalopram can be achieved within 2 to 4 hours after daily dosing. The protein binding rate was less than 80%. Drugs and metabolites can cross the placental barrier, and the distribution in the fetus is similar to the maternal. Lactating women taking this medicine will have a small amount of drugs and their metabolites through breast milk into the baby's body. The biological half-life is approximately one and a half days. Excretion process through urine and feces. |
| applicable symptoms | This product has antidepressant effect. Good efficacy in patients with endogenous and non-endogenous depression. Its antidepressant effect is usually established after 2 to 4 weeks. Citalopram does not affect the cardiac conduction system and blood pressure, especially for elderly patients is particularly important. The rare side effects and most mild sedative properties of this product make it particularly suitable for long-term treatment. And the drug does not cause weight gain, nor does it strengthen the effect of alcohol. Applies to depressive Mental Disorder (endogenous and non-endogenous depression). (2016-01-22) |
| adverse reactions | adverse reactions of this product are usually transient and mild. It is usually evident in the first or second week after taking the drug, and generally disappears gradually with the improvement of depressive symptoms. Common adverse reactions are: 1. Nausea, dry mouth, dizziness, Head Pain, drowsiness, shorten sleep time, sweating, salivation, tremor, Diarrhea. Can cause hormone secretion disorder, mania, tachycardia and orthostatic hypotension. There are reports of epileptic seizures. Studies have shown that can cause sexual dysfunction. |
| note | 1. Epilepsy, manic history, severe renal dysfunction, liver dysfunction, recent onset of myocardial infarction patients should be used with caution. Concomitant use with monoamine oxidase inhibitors can cause severe or fatal reactions, and the combination of the two drugs is prohibited. Stop taking either drug for at least 14 days before taking the other. A tendency of Suicide may persist until significant depression remission occurs. If the patient enters the manic phase, should stop the goods, and give the spirit of inhibition drugs for appropriate treatment. 4. May lead to hyponatremia and Syndrome of inappropriate secretion of antidiuretic hormone, the course of medication should be closely monitored the symptoms of the above diseases, and timely withdrawal, take appropriate measures. Patients using this product should avoid operating dangerous machinery, including driving vehicles. 6. Patients using this product should not take alcohol-containing products at the same time. 7. The safety of this product for human pregnancy has not been determined, unless the benefits to the patient far exceeds the theoretical risk to the fetus or baby, otherwise should not be taken during pregnancy and lactation. FDA's pregnancy safety rating for this drug is C. Safety and efficacy in children have not been established. |
| usage and dosage | This product has different dosage for people of different ages. Adults: Citalopram Hydrobromide Tablets are taken once daily. The starting dose is 1 tablet per day (20mg), which can be increased to 2 tablets per day (40mg) or the maximum dose of 3 tablets per day (60mg) if clinically indicated. Patients over 65 years of age: the dose is halved by 0.5 to 1.5 tablets (10 to 30mg) daily. Antidepressant treatment belongs to symptomatic treatment, must last for a long time, generally for manic depression Mental Disorder need 4 to 6 months. In case of Sleep Initiation and Maintenance Disorders or severe akathisia, supplementary sedative treatment is recommended in the acute phase. |
| Use | The second generation antidepressant has a strong and specific inhibitory effect on serotonin reabsorption inhibition. For anti-depression, senile dementia and multi-infarct dementia. |
| production method | 21g of 50% sodium hydride (dissolved in mineral oil) was dissolved in 90ml of dimethyl sulfoxide under nitrogen at 60-70 °c, A sodium methylsulfinate solution was obtained. Under cooling, drop a solution of 96g of 1-(4-fluorophenyl)-1 dihydro-s-isobenzofuran nitrile in 150ml of dimethyl sulfoxide, the temperature of the reaction solution was maintained at 25 °c. After addition, the mixture was stirred at room temperature for 10min. A solution of 53g of 3-dimethylaminopropyl chloride in 25ml of disulfoxide was rapidly added and heated to 40 °c for 50min. The reaction mixture was poured into ice water and extracted with ether. The ether extract was further extracted with 20% aqueous acetic acid. The aqueous acetic acid extract was basified with 10mol/L sodium hydroxide and extracted with ether. The ether extract was washed with water for several times, dried with anhydrous potassium carbonate, and concentrated in vacuo by active decoloration. The residue was an oil (80g) which, after vacuum distillation, gave 56g of citalopram. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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