1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide

• ChemBase ID: 72645
• Molecular Formular: C20H22BrFN2O
• Molecular Mass: 405.3038832
• Monoisotopic Mass: 404.08995355
• SMILES: c1(ccc(cc1)C1(c2c(CO1)cc(cc2)C#N)CCCN(C)C)F.Br
• Canonical SMILES: N#Cc1ccc2c(c1)COC2(CCCN(C)C)c1ccc(cc1)F.Br
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide
• IUPAC Traditional name: citalopram hydrobromide; recital hydrobromide; 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide
• Synonyms: 1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile hydrobromide; Citalopram hydrobromide; Celexa; Cipramil; Citalopram Hydrobromide; (S)-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile hydrobromide; Nitalapram, LU-10-171, 1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dizohydro-5-isobenzofurancarbonitrile Hydrobromide Salt; Citalopram, Hydrobromide Salt

Database IDs

• CAS Number: 59729-32-7; 59729-33-8
• EC Number: 261-890-6
• MDL Number: MFCD02101306
• PubChem SID: 162037570; 24278335
• PubChem CID: 77995

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.3290631
• LogD (pH = 7.4): 1.409549
• Log P: 3.7643042
• Molar Refractivity: 94.0202 cm^3
• Polarizability: 35.7618 Å^3
• Polar Surface Area: 36.26 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: solid; White Solid
• Melting Point: 177-179°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: NP6313500
• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: SSR
• Gene Information: human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR4(3360), HTR5A(3361), HTR5B(645694), HTR6(3362), HTR7(3363)
• Mechanism of Action: 5HT re-uptake inhibitor

Product Information

• Salt Data: HBr; Hydrobromide
• Application(s): Antidepressant Drug
• Empirical Formula (Hill Notation): C20H21FN2O · HBr

DETAILS

Selleck Chemicals - S1372

Research Area: Neurological Disease
Biological Activity:
Citalopram (Celexa, Cipramil) is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. Most often used to treat major depression, it is also used on occasion in the treatment of body dysmorphic disorder, anxiety, and panic disorder. [1]

Sigma Aldrich - C7861

Biochem/physiol Actions
Potent and selective serotonin uptake inhibitor (Ki = 5.4 nM); antidepressant

Toronto Research Chemicals - C505000

An inhibitor of serotonin (5-HT) uptake. Used as an antidepressant.

REFERENCES

• http://en.wikipedia.org/wiki/Citalopram
• Christensen, A.V., et al.: Eur. J. Pharmacol., 41, 153 (1977)
• Keller, M.B., et al.: J. Clin. Psychiatry, 61, 896 (1977)
• Von Moltke, L.L., et al.: Drug Metab. Dispos., 29, 1102 (1977)
• Bigler, A.J. et al., Eur. J. Med. Chem. (Chim. Ther.), 1977, 12, 289, (synth, pharmacol)
• Christensen, A.V. et al., Eur. J. Pharmacol., 1977, 41, 153, (pharmacol)
• Ger. Pat., 1977, 2 657 013; CA, 87, 135040e, (synth)
• Koch, H., Pharm. Int., 1980, 1, 66, (rev, pharmacol)
• Kragh-Soerensen, P. et al., Acta Pharmacol. Toxicol., 1981, 48, 53, (metab)
• Boeck, V. et al., Acta Pharmacol. Toxicol., 1982, 50, 169, (tox)
• Hyttel, J., Dev. Psychiatry, 1986, 7, 820, (rev, pharmacol)
• Eur. Pat., 1989, Lundbeck, 347 066; CA, 113, 78150v, (isomers, synth, pharmacol)
• Goa, K.L. et al., Drugs, 1991, 41, 450, (rev)
• Noble, S. et al., CNS Drugs, 1997, 8, 410-431, (rev)
• Sidhu, J. et al., Chirality, 1997, 9, 686-692, (pharmacol, enantiomers)
• Rochat, B. et al., Brain Res., 1999, 831, 229-236, (pharmacol)
• Popik, P., J. Clin. Psychopharmacol., Suppl. 1, 1999, 19, 4S-22S, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 281
• Pat. Coop. Treaty (WIPO), 2000, Lundbeck, 00 23 431; CA, 132, 308238d, (synth)