(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile; oxalic acid

• ChemBase ID: 154953
• Molecular Formular: C22H23FN2O5
• Molecular Mass: 414.4268232
• Monoisotopic Mass: 414.15910007
• SMILES: CN(C)CCC[C@@]1(c2ccc(cc2CO1)C#N)c1ccc(cc1)F.C(=O)(C(=O)O)O
• Canonical SMILES: OC(=O)C(=O)O.N#Cc1ccc2c(c1)CO[C@@]2(CCCN(C)C)c1ccc(cc1)F
• InChI: InChI=1S/C20H21FN2O.C2H2O4/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;3-1(4)2(5)6/h4-9,12H,3,10-11,14H2,1-2H3;(H,3,4)(H,5,6)/t20-;/m0./s1
• InChIKey: KTGRHKOEFSJQNS-BDQAORGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile; oxalic acid
• IUPAC Traditional name: lexapro; oxalic acid
• Synonyms: S-(+)-Citalopram oxalate; S-(+)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile oxalate; Escitalopram oxalate; (1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile Ethanedioate; Escitalopram Oxalate; (S)-(+)-Citalopram Oxalate; Cipralex; (S)-Citalopram Oxalate

Database IDs

• CAS Number: 219861-08-2
• MDL Number: MFCD06407826
• PubChem SID: 162249091
• PubChem CID: 146571

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: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: ≥15 mg/mL; Methanol
• Apperance: White Solid; white to tan powder
• Melting Point: 152-153°C

Safety Information

• Storage Condition: -20°C Freezer; desiccated
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H21FN2O · C2H2O4

DETAILS

Sigma Aldrich - E4786

Biochem/physiol Actions
Escitalopram is a selective serotonin reuptake inhibitor (SSRI), the S-enantiomer and eutomer of citalopram.

Toronto Research Chemicals - C505010

An inhibitor of serotonin (5-HT) uptake. Antidepressant.

REFERENCES

• 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)