Chemistry:Adatanserin

Adatanserin
Clinical data
ATC code	none;
Identifiers
	IUPAC name N-[2-(4-pyrimidin-2-ylpiperazin-1-yl)ethyl]adamantane-1-carboxamide;
CAS Number	127266-56-2 ;
PubChem CID	130918;
ChemSpider	115774 ;
UNII	W5U6WQM26H;
ChEMBL	ChEMBL2107510 ;
Chemical and physical data
Formula	C21H31N5O
Molar mass	369.513 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(NCCN2CCN(c1ncccn1)CC2)C35CC4CC(CC(C3)C4)C5;
	InChI InChI=1S/C21H31N5O/c27-19(21-13-16-10-17(14-21)12-18(11-16)15-21)22-4-5-25-6-8-26(9-7-25)20-23-2-1-3-24-20/h1-3,16-18H,4-15H2,(H,22,27) ; Key:HPFLVTSWRFCPCV-UHFFFAOYSA-N ;
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Short description: Chemical compound

Adatanserin (WY-50,324, SEB-324) is a mixed 5-HT_1A receptor partial agonist and 5-HT_2A and 5-HT_2C receptor antagonist.^[1]^[2]^[3] It was under development by Wyeth as an antidepressant but was ultimately not pursued.^[3]^[4]

Adantaserin has been shown to be neuroprotective against ischemia-induced glutamatergic excitotoxicity, an effect which appears to be mediated by blockade of the 5-HT_2A receptor.^[5]

References

↑ "Antidepressant-like activity of compounds with varying efficacy at 5-HT1A receptors". Neuropharmacology 32 (4): 331–40. April 1993. doi:10.1016/0028-3908(93)90153-T. PMID 8497336.
↑ "Pharmacological characterization of in vivo properties of putative mixed 5-HT1A agonist/5-HT2A/2C antagonist anxiolytics. I. Antipunishment effects in the pigeon". The Journal of Pharmacology and Experimental Therapeutics 276 (2): 388–97. February 1996. PMID 8632301. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8632301.
↑ ^3.0 ^3.1 "Synthesis and SAR of adatanserin: novel adamantyl aryl- and heteroarylpiperazines with dual serotonin 5-HT(1A) and 5-HT(2) activity as potential anxiolytic and antidepressant agents". Journal of Medicinal Chemistry 42 (25): 5077–94. December 1999. doi:10.1021/jm9806704. PMID 10602693.
↑ Stahl, S. M. (2000). Essential psychopharmacology: neuroscientific basis and practical application. Cambridge, UK: Cambridge University Press. p. 262. ISBN 0-521-64615-4. https://archive.org/details/essentialpsychop00step. "adatanserin."
↑ "Attenuation of ischemic efflux of endogenous amino acids by the novel 5-HT(1A)/5-HT(2) receptor ligand adatanserin". Neurochemistry International 40 (3): 203–9. March 2002. doi:10.1016/S0197-0186(01)00082-1. PMID 11741003.

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[pmid8497336-1] "Antidepressant-like activity of compounds with varying efficacy at 5-HT1A receptors". Neuropharmacology 32 (4): 331–40. April 1993. doi:10.1016/0028-3908(93)90153-T. PMID 8497336.

[pmid8632301-2] "Pharmacological characterization of in vivo properties of putative mixed 5-HT1A agonist/5-HT2A/2C antagonist anxiolytics. I. Antipunishment effects in the pigeon". The Journal of Pharmacology and Experimental Therapeutics 276 (2): 388–97. February 1996. PMID 8632301. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8632301.

[pmid10602693-3] 3.0 ^3.1 "Synthesis and SAR of adatanserin: novel adamantyl aryl- and heteroarylpiperazines with dual serotonin 5-HT(1A) and 5-HT(2) activity as potential anxiolytic and antidepressant agents". Journal of Medicinal Chemistry 42 (25): 5077–94. December 1999. doi:10.1021/jm9806704. PMID 10602693.

[isbn0-521-64615-4-4] Stahl, S. M. (2000). Essential psychopharmacology: neuroscientific basis and practical application. Cambridge, UK: Cambridge University Press. p. 262. ISBN 0-521-64615-4. https://archive.org/details/essentialpsychop00step. "adatanserin."

[pmid11741003-5] "Attenuation of ischemic efflux of endogenous amino acids by the novel 5-HT(1A)/5-HT(2) receptor ligand adatanserin". Neurochemistry International 40 (3): 203–9. March 2002. doi:10.1016/S0197-0186(01)00082-1. PMID 11741003.

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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 N-[2-(4-pyrimidin-2-ylpiperazin-1-yl)ethyl]adamantane-1-carboxamide
CAS Number	127266-56-2^N
PubChem CID	130918
ChemSpider	115774^Y
UNII	W5U6WQM26H
ChEMBL	ChEMBL2107510^N
Chemical and physical data
Formula	C₂₁H₃₁N₅O
Molar mass	369.513 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(NCCN2CCN(c1ncccn1)CC2)C35CC4CC(CC(C3)C4)C5
InChI InChI=1S/C21H31N5O/c27-19(21-13-16-10-17(14-21)12-18(11-16)15-21)22-4-5-25-6-8-26(9-7-25)20-23-2-1-3-24-20/h1-3,16-18H,4-15H2,(H,22,27)^Y Key:HPFLVTSWRFCPCV-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

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