Name: Citalopram
SKU: 59729-33-8

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Basic Information

Molecular Structure:
CAS No.:	59729-33-8
Name:	Citalopram
Article Data:	57

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

Synthetic route

: 59729-32-7
citalopram hydrobromide

: 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions

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

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

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

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;

: dl-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-5-bromo-1,3-dihydroisobenzofuran oxalate salt

: 544-92-3
copper(I) cyanide

: 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions

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

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;

: potassium cyanide

: 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

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

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%

aqueous ethylenediamine: aqueous ethylenediamine

: 64169-39-7
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine

: copper(l) cyanide

: 7440-44-0
pyrographite

: 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; toluene	84%

...Expand

: 64169-39-7
3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine

: copper(l) cyanide

: 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 24h; Rosenmund-van Braun Cyanation; Sealed tube; Inert atmosphere;	74%

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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.

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.