Cas no 128196-02-1 ((R)-(-)-Citalopram)

(R)-(-)-Citalopram is the enantiomer of the widely used selective serotonin reuptake inhibitor (SSRI) citalopram. As the biologically active isomer, it exhibits higher potency and selectivity for serotonin transporter (SERT) inhibition compared to its (S)-(+)-counterpart. This compound is of significant interest in pharmacological research due to its potential for improved efficacy and reduced side effects in the treatment of depression and anxiety disorders. Its enantiomeric purity makes it a valuable reference standard for analytical and preclinical studies. (R)-(-)-Citalopram is also utilized in investigations of stereoselective metabolism and receptor binding interactions, contributing to a deeper understanding of SSRI mechanisms.
(R)-(-)-Citalopram structure
(R)-(-)-Citalopram structure
Product Name:(R)-(-)-Citalopram
CAS No:128196-02-1
MF:C20H21FN2O
MW:324.391948461533
CID:139266
PubChem ID:6101829
Update Time:2025-06-29

(R)-(-)-Citalopram Chemical and Physical Properties

Names and Identifiers

    • 5-Isobenzofurancarbonitrile,1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-, (1R)-
    • (R)-(-)-CITALOPRAM
    • (-)-Citalopram
    • (R)-(-)-3-(5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine
    • (R)-2-Phenylpropi
    • (R)-2-phenylpropionamide
    • (R)-2-Phenyl-propionsaeure-amid
    • (R)-citalopram
    • 3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid
    • AG-D-83089
    • Benzeneacetamide, a-methyl-, (aR)-
    • Hydratropamide,(R)-(-)- (8CI)
    • R(-)citalopram
    • R(-)-citalopram
    • R-3-(2-carboxypiperazin-4-yl)-propyl-1-phosphonic acid
    • R-citalopram
    • BDBM86046
    • DTXSID201317195
    • PDSP1_001303
    • HMS2231B13
    • (R)-1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
    • NCGC00389194-01
    • SMR000550474
    • Q27116962
    • Citalopram, (R)-
    • 5-Isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, (1R)-
    • UNII-1TH2C9NJHL
    • 128196-02-1
    • AKOS015914557
    • EN300-49846
    • BIDD:PXR0176
    • (1R)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile
    • HMS3369A13
    • CHEBI:36792
    • (1R)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
    • 1TH2C9NJHL
    • SCHEMBL13235283
    • PDSP2_001287
    • CHEMBL399730
    • MLS001165696
    • BIDD:GT0160
    • (R)-(-)-Citalopram
    • Inchi: 1S/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/t20-/m1/s1
    • InChI Key: WSEQXVZVJXJVFP-HXUWFJFHSA-N
    • SMILES: FC1C=CC(=CC=1)[C@@]1(C2C=CC(C#N)=CC=2CO1)CCCN(C)C

Computed Properties

  • Exact Mass: 324.16393
  • Monoisotopic Mass: 324.164
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 24
  • Rotatable Bond Count: 5
  • Complexity: 466
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 36.3A^2
  • XLogP3: 3.2

Experimental Properties

  • PSA: 36.26
  • LogP: 3.81298

(R)-(-)-Citalopram Pricemore >>

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Additional information on (R)-(-)-Citalopram

Introduction to (R)-(-)-Citalopram and Its CAS No. 128196-02-1

Compound with the CAS number 128196-02-1 is a significant entity in the field of pharmaceutical chemistry, particularly known for its relationship to the widely recognized antidepressant drug, (R)-(-)-Citalopram. This compound is a stereoisomer of citalopram, which has garnered considerable attention due to its unique pharmacological properties and therapeutic applications. The detailed exploration of this compound not only sheds light on its chemical structure but also delves into its biological activity, mechanism of action, and recent advancements in research.

The chemical structure of (R)-(-)-Citalopram is characterized by a bicyclic piperazine ring system linked to a benzene ring, with an amine group and a chiral center at the stereogenic carbon. This configuration is crucial for its pharmacological effects, as the stereochemistry of the molecule plays a pivotal role in determining its biological activity. The CAS number 128196-02-1 specifically identifies this enantiomer, distinguishing it from other stereoisomers such as the (S)-(+)-enantiomer, which is less active or inactive in terms of therapeutic efficacy.

In recent years, there has been a surge in research focused on understanding the pharmacological mechanisms of (R)-(-)-Citalopram. Studies have indicated that this compound exerts its antidepressant effects primarily by inhibiting the reuptake of serotonin, a key neurotransmitter involved in mood regulation. This mechanism is similar to other selective serotonin reuptake inhibitors (SSRIs), but the stereochemical purity of (R)-(-)-Citalopram offers several advantages in terms of efficacy and reduced side effects.

One of the most compelling aspects of (R)-(-)-Citalopram is its potential for developing more targeted and effective treatments for mental health disorders. Research has shown that the (R)-enantiomer may have a higher affinity for serotonin receptors compared to the (S)-enantiomer, leading to improved therapeutic outcomes. This has prompted investigations into optimizing drug formulations that utilize this enantiomer exclusively or in higher concentrations.

The synthesis and characterization of compounds like (R)-(-)-Citalopram with CAS number 128196-02-1 have been facilitated by advancements in chiral synthesis techniques. These methods allow for the precise control of stereochemistry during drug production, ensuring high purity and efficacy. The development of asymmetric catalysis and biocatalytic processes has been particularly instrumental in achieving these milestones.

Recent clinical trials have highlighted the promising potential of (R)-(-)-Citalopram in treating various psychiatric disorders beyond depression. Studies have explored its efficacy in managing anxiety disorders, obsessive-compulsive disorder (OCD), and even some neurodegenerative conditions. The compound's ability to modulate serotonin levels not only addresses mood disorders but also interacts with other neurotransmitter systems, making it a versatile therapeutic agent.

The pharmacokinetic profile of (R)-(-)-Citalopram is another area of active research. Understanding how this compound is absorbed, distributed, metabolized, and excreted by the body is crucial for optimizing dosing regimens and minimizing adverse effects. Advanced analytical techniques such as mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy have enabled researchers to gain detailed insights into these processes.

In conclusion, the compound identified by CAS number 128196-02-1, known as (R)-(-)-Citalopram, represents a significant advancement in pharmaceutical chemistry. Its unique stereochemistry and potent pharmacological effects make it a valuable tool in the treatment of various mental health disorders. Ongoing research continues to uncover new applications and improve our understanding of its mechanisms of action, paving the way for more effective and targeted therapies.

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