CSP-2503

{{Drugbox

| verifiedrevid = 414040667

| IUPAC_name = 2-[(4-naphthalen-1-ylpiperazin-1-yl)methyl]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

| image = CSP-2503-structure.png

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 581813-10-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 87UKL3XE5X

| ATC_prefix = none

| ATC_suffix =

| PubChem = 10317515

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8492979

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 285066

| C=22 | H=26 | N=4 | O=2

| smiles = O=C4N5CCCC5C(=O)N(CN3CCN(c2c1ccccc1ccc2)CC3)C4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CTZWGZSINBFHFD-UHFFFAOYSA-N

}}

CSP-2503 is a potent and selective 5-HT_1A receptor agonist, 5-HT_2A receptor antagonist, and 5-HT₃ receptor antagonist of the naphthylpiperazine class.{{cite journal |vauthors=Delgado M, Caicoya AG, Greciano V | title = Anxiolytic-like effect of a serotonergic ligand with high affinity for 5-HT1A, 5-HT2A and 5-HT3 receptors | journal = European Journal of Pharmacology | volume = 511 | issue = 1 | pages = 9–19 |date=March 2005 | pmid = 15777774 | doi = 10.1016/j.ejphar.2005.01.032 |display-authors=etal}} First synthesized in 2003, it was designed based on computational models and QSAR studies.{{cite journal |vauthors=López-Rodríguez ML, Morcillo MJ, Fernández E | title = 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 effects, and thus has been suggested as a treatment for anxiety in humans with a multimodal mechanism of action.

References