Chemistry:CSP-2503

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	581813-10-7;
PubChem CID	10317515;
ChemSpider	8492979 ;
UNII	87UKL3XE5X;
ChEMBL	ChEMBL285066 ;
Chemical and physical data
Formula	C22H26N4O2
Molar mass	378.476 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:CTZWGZSINBFHFD-UHFFFAOYSA-N ;
	(verify)

Short description: Chemical compound

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.^[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]

References

↑ ^1.0 ^1.1 "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. March 2005. doi:10.1016/j.ejphar.2005.01.032. PMID 15777774.
↑ Design and synthesis of S-(−)-2-<nowiki>journal = Bioorganic & Medicinal Chemistry Letters. 13. April 2003. pp. 1429–32. doi:10.1016/S0960-894X(03)00160-4. PMID 12668005.
↑ "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. April 2005. doi:10.1021/jm048999e. PMID 15801844.

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Original source: https://en.wikipedia.org/wiki/CSP-2503. Read more

[pmid15777774-1] 1.0 ^1.1 "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. March 2005. doi:10.1016/j.ejphar.2005.01.032. PMID 15777774.

[pmid12668005-2] Design and synthesis of S-(−)-2-<nowiki>journal = Bioorganic & Medicinal Chemistry Letters. 13. April 2003. pp. 1429–32. doi:10.1016/S0960-894X(03)00160-4. PMID 12668005.

[pmid15801844-3] "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. April 2005. doi:10.1021/jm048999e. PMID 15801844.

[1]

[2]

[3]

v t e Anxiolytics (N05B)
5-HT_1AR agonists	Buspirone Gepirone^† Tandospirone
GABA_AR PAMs	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Chlormezanone^‡ Ethanol (alcohol) Etifoxine Imepitoin; Herbs: Kava Skullcap Valerian
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIs (e.g., escitalopram) SNRIs (e.g., duloxetine) SARIs (e.g., trazodone) TCAs (e.g., clomipramine^#) TeCAs (e.g., mirtazapine) MAOIs (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e Piperazines
Simple piperazines (no additional rings)	1-Cyclohexylpiperazine Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide Piberaline Piribedil Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine Azimilide Cinepazet Cinepazic acid Cinepazide Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

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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	581813-10-7
PubChem CID	10317515
ChemSpider	8492979^Y
UNII	87UKL3XE5X
ChEMBL	ChEMBL285066^Y
Chemical and physical data
Formula	C₂₂H₂₆N₄O₂
Molar mass	378.476 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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