Chemistry:ORG-12962

ORG-12962
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine;
CAS Number	210821-63-9 ;
PubChem CID	9796408;
IUPHAR/BPS	170;
ChemSpider	7972174 ;
ChEMBL	ChEMBL506999 ;
Chemical and physical data
Formula	C10H11ClF3N3
Molar mass	265.66 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C2CNCCN2c(nc1Cl)ccc1C(F)(F)F;
	InChI InChI=1S/C10H11ClF3N3/c11-9-7(10(12,13)14)1-2-8(16-9)17-5-3-15-4-6-17/h1-2,15H,3-6H2 ; Key:QZYYPQAYSFBKPW-UHFFFAOYSA-N ;
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Short description: Chemical compound

ORG-12962 is a pyridinylpiperazine drug developed by Organon, which acts as a potent and selective agonist for the 5-HT₂ receptor family, with highest affinity at 5-HT_2C and lowest at 5-HT_2B subtypes.^[1] It was developed as a potential anti-anxiety drug, but was discontinued from human trials after tests in a public speaking challenge showed that its anti-anxiety effects were accompanied by side effects such as dizziness and a "spacey" feeling, which were attributed to poor selectivity in vivo over the hallucinogenic 5-HT_2A receptor.^[2]

References

↑ "Functional characterization of agonists at recombinant human 5-HT2A, 5-HT2B and 5-HT2C receptors in CHO-K1 cells". British Journal of Pharmacology 128 (1): 13–20. September 1999. doi:10.1038/sj.bjp.0702751. PMID 10498829.
↑ "5-HT2C ligands: recent progress". Progress in Medicinal Chemistry 46: 281–390. 2008. doi:10.1016/S0079-6468(07)00006-9. ISBN 9780444530189. PMID 18381128.

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[pmid10498829-1] "Functional characterization of agonists at recombinant human 5-HT2A, 5-HT2B and 5-HT2C receptors in CHO-K1 cells". British Journal of Pharmacology 128 (1): 13–20. September 1999. doi:10.1038/sj.bjp.0702751. PMID 10498829.

[pmid18381128-2] "5-HT2C ligands: recent progress". Progress in Medicinal Chemistry 46: 281–390. 2008. doi:10.1016/S0079-6468(07)00006-9. ISBN 9780444530189. PMID 18381128.

[1]

[2]

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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Legal status

Legal status	In general: uncontrolled
Identifiers
IUPAC name 1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine
CAS Number	210821-63-9^N
PubChem CID	9796408
IUPHAR/BPS	170
ChemSpider	7972174^Y
ChEMBL	ChEMBL506999^Y
Chemical and physical data
Formula	C₁₀H₁₁ClF₃N₃
Molar mass	265.66 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C2CNCCN2c(nc1Cl)ccc1C(F)(F)F
InChI InChI=1S/C10H11ClF3N3/c11-9-7(10(12,13)14)1-2-8(16-9)17-5-3-15-4-6-17/h1-2,15H,3-6H2^Y Key:QZYYPQAYSFBKPW-UHFFFAOYSA-N^Y
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