Products Categories
| CAS No.: | 59729-33-8 |
|---|---|
| Name: | Citalopram |
| Article Data: | 57 |
| Molecular Structure: | |
|
|
|
| Formula: | C20H21FN2O |
| Molecular Weight: | 324.398 |
| Synonyms: | 1-(3-Dimethylaminopropyl)-1-(4-fluorophenyl)-5-cyanophthalan;1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile;Bonitrile;Lu 10-171;Nitalapram; |
| EINECS: | 261-891-1 |
| Density: | 1.18 g/cm3 |
| Melting Point: | 182-183 °C |
| Boiling Point: | 428.3 °C at 760 mmHg |
| Flash Point: | 212.8 °C |
| Appearance: | grease |
| Transport Information: | UN 3249 |
| PSA: | 36.26000 |
| LogP: | 3.81298 |
- 81281-59-67-Benzylideneaminotheophylline
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 68439-39-4Poly(oxy-1,2-ethanediyl), alpha-(2-ethylhexyl)-omega-hydroxy-,
- 852475-26-4MC1568
- 958254-66-51H-Imidazo[4,5-b]pyridine-2-carboxaldehyde, 1-methyl-, hydrochloride
- 99170-93-1N-Methyl-2-oxazolamine
- 717878-06-31-(4-fluorophenyl)-4-nitro-1H-imidazole
- 914458-26-7[5-(2-fluorophenyl)-1-pentyl-1H-pyrrol-3-yl]-1-naphthalenyl-Methanone
- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
- 59729-32-7
citalopram hydrobromide
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water | 100% |
| With sodium hydroxide In water; toluene for 0.25h; pH=10; | 93% |
| With ammonia In water at 20℃; for 3h; pH=9; Product distribution / selectivity; | |
| With sodium hydroxide In water; toluene at 20℃; pH=9 - 10; Industry scale; |
- 445312-08-3
3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile
- 19070-16-7
3-(N,N-dimethylamino)propylmagnesium chloride
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| With ammonium chloride In tetrahydrofuran; water; toluene | 95% |
| With hydrogen bromide In tetrahydrofuran; 1,2-dimethoxyethane | 75% |
- 64169-67-1
1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
- 109-54-6
3-(Dimethylamino)propyl chloride
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| Stage #1: 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; 3-(Dimethylamino)propyl chloride With sodium hydride In 1,3-dimethyl-2-imidazolidinone; toluene at 40 - 50℃; for 0.666667h; Stage #2: With hydrogenchloride; water at 65 - 70℃; for 3h; Stage #3: With sodium hydroxide In water; toluene Product distribution / selectivity; | 93% |
| Stage #1: 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; 3-(Dimethylamino)propyl chloride With sodium hydride In tetrahydrofuran; toluene at 40 - 50℃; for 0.666667h; Stage #2: With dimethyl sulfoxide at 65 - 70℃; for 3h; Stage #3: With acetic acid In water; toluene Product distribution / selectivity; | 51.6% |
| With sodium hydride In dimethyl sulfoxide; toluene at 20 - 25℃; for 3h; Product distribution / selectivity; |
- 64372-56-1
1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| With trichlorophosphate In acetonitrile at 60℃; Heating / reflux; | 92% |
| Stage #1: 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide With thionyl chloride In toluene at 85 - 95℃; for 1h; Stage #2: With ammonia In water; toluene pH=7.5 - 7.8; Purification / work up; |
- 544-92-3
copper(I) cyanide
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| Stage #1: dl-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-5-bromo-1,3-dihydroisobenzofuran oxalate salt; copper(I) cyanide With copper(l) iodide In DMF (N,N-dimethyl-formamide) at 145 - 150℃; for 28h; Stage #2: With ethylenediamine In DMF (N,N-dimethyl-formamide); water at 25 - 30℃; for 2h; | 87% |
- 103146-25-4
4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| Stage #1: 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile With phosphoric acid In toluene at 80℃; for 2.5h; Stage #2: With sodium hydroxide In water; toluene at 50℃; pH=10; | 86% |
| With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃; for 3h; | 55% |
| With triphenylphosphine; sodium t-butanolate; diethylazodicarboxylate In tetrahydrofuran at 0℃; | |
| With sulfuric acid In water at 70℃; for 6h; Product distribution / selectivity; |
- 64169-39-7
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| Stage #1: potassium cyanide With acetic acid In ethylene glycol Sealed tube; Stage #2: 3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine With P(t-Bu)3 Palladacycle Gen. 3; potassium acetate In 1,4-dioxane; water at 60℃; for 16h; Sealed tube; | 86% |
- 64169-39-7
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| Stage #1: 3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine With sodium cyanide; copper(I) cyanide In DMF (N,N-dimethyl-formamide); toluene at 154 - 159℃; Heating / reflux; Stage #2: With sodium cyanide In DMF (N,N-dimethyl-formamide); water at 60 - 70℃; Stage #3: With ethylenediamine In DMF (N,N-dimethyl-formamide); water; toluene | 84% |
- 64169-39-7
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
- 7440-44-0
pyrographite
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide; toluene | 84% |
- 64169-39-7
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
- 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide at 150℃; for 24h; Rosenmund-van Braun Cyanation; Sealed tube; Inert atmosphere; | 74% |
What can I do for you?
Get Best Price
History
Citalopram (CAS NO.59729-33-8) (pronounced /sa??tæl?præm/) was originally created in 1989by the pharmaceutical company Lundbeck. The patent expired in 2003, allowing other companies to legally produce generic versions. Lundbeck has recently released an updated formulation called escitalopram (also known as Cipralex or Lexapro), which is the S-enantiomer of the racemic citalopram (see b), and acquired a new patent for it. In the United States, Forest Labs manufactures and markets the drug.
Specification
The IUPAC name of Citalopram is 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile. With the CAS registry number 59729-33-8, it is also named as 5-Isobenzofurancarbonitrile, 1,3-dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-. The classification codes are Antidepressive Agents; Antidepressive agents, second-generation; Central Nervous System Agents; Drug / Therapeutic Agent; Human Data; Neurotransmitter Agents; Neurotransmitter Uptake Inhibitors; Psychotropic Drugs; Serotonin Agents; Serotonin uptake inhibitors. It is grease which can be crystallized from isopropanol.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.54; (4)ACD/LogD (pH 7.4): 0.39; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 4.19; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.591; (13)Molar Refractivity: 92.13 cm3; (14)Molar Volume: 272.6 cm3; (15)Polarizability: 36.52×10-24 cm3; (16)Surface Tension: 49.8 dyne/cm; (17)Enthalpy of Vaporization: 68.35 kJ/mol; (18)Vapour Pressure: 1.53E-07 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Exact Mass: 324.163792; (21)MonoIsotopic Mass: 324.163792; (22)Topological Polar Surface Area: 36.3; (23)Heavy Atom Count: 24; (24)Complexity: 466.
Preparation of Citalopram: It can be obtained by 1-(4-fluorophenyl) -1,3-dihydro-S-isobenzofuran nitrile.
.gif)
.gif)
Uses of Citalopram: It is highly selective and potent 5-HT uptake inhibitor with no effect on noradrenalin or dopamine uptake (IC 50 values are 1.8, 8800 and 41000 nM respectively). It also has negligible activity at a wide range of receptors and is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class to treat major depression. What's more, this drug is frequently used off-label to treat anxiety, panic disorder, ADHD, PMDD, Body dysmorphic disorder and OCD.
People can use the following data to convert to the molecule structure.
1. SMILES:Fc1ccc(cc1)C3(OCc2cc(C#N)ccc23)CCCN(C)C
2. InChI:InChI=1/C20H21FN2O/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
3. InChIKey:WSEQXVZVJXJVFP-UHFFFAOYAV
The following are the toxicity data which has been tested.
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| human | TDLo | oral | 4571ug/kg/8D- (4.571mg/kg) | BEHAVIORAL: SLEEP BEHAVIORAL: HEADACHE GASTROINTESTINAL: NAUSEA OR VOMITING | Human Psychopharmacology. Vol. 12, Pg. 119, 1997. |
| man | LDLo | oral | 56mg/kg (56mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Lancet. Vol. 348, Pg. 339, 1996. |
| mouse | LD50 | intraperitoneal | 179mg/kg (179mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Journal of Pharmacy and Pharmacology. Vol. 49, Pg. 1019, 1997. |