CSP-2503

CSP-2503 is a potent and selective 5-HT1A receptor agonist, 5-HT2A receptor antagonist, and 5-HT3 receptor antagonist of the phenylpiperazine class.[1] First synthesized in 2003, it was designed based on computational models and QSAR studies.[2][3] In rat studies, CSP-2503 has demonstrated anxiolytic effects, and thus has been suggested as a treatment for anxiety in humans with a multimodal mechanism of action.[1]

CSP-2503
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 2-[(4-naphthalen-1-ylpiperazin-1-yl)methyl]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC22H26N4O2
Molar mass378.476 g·mol−1
3D model (JSmol)
SMILES
  • O=C4N5CCCC5C(=O)N(CN3CCN(c2c1ccccc1ccc2)CC3)C4
InChI
  • InChI=1S/C22H26N4O2/c27-21-15-25(22(28)20-9-4-10-26(20)21)16-23-11-13-24(14-12-23)19-8-3-6-17-5-1-2-7-18(17)19/h1-3,5-8,20H,4,9-16H2 Y
  • Key:CTZWGZSINBFHFD-UHFFFAOYSA-N Y
  (verify)

See also

References
  1. Delgado M, Caicoya AG, Greciano V, et al. (March 2005). "Anxiolytic-like effect of a serotonergic ligand with high affinity for 5-HT1A, 5-HT2A and 5-HT3 receptors". European Journal of Pharmacology. 511 (1): 9–19. doi:10.1016/j.ejphar.2005.01.032. PMID 15777774.
  2. López-Rodríguez ML, Morcillo MJ, Fernández E, et al. (April 2003). "Design and synthesis of S-(−)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2-a]pyrazine (CSP-2503) using computational simulation. A 5-HT1A receptor agonist". Bioorganic & Medicinal Chemistry Letters. 13 (8): 1429–32. doi:10.1016/S0960-894X(03)00160-4. PMID 12668005.
  3. López-Rodríguez ML, Morcillo MJ, Fernández E, et al. (April 2005). "Synthesis and structure-activity relationships of a new model of arylpiperazines. 8. Computational simulation of ligand-receptor interaction of 5-HT(1A)R agonists with selectivity over alpha1-adrenoceptors". Journal of Medicinal Chemistry. 48 (7): 2548–58. doi:10.1021/jm048999e. PMID 15801844.
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