ORG-12962

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-HT2C and lowest at 5-HT2B 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-HT2A receptor.[2]

ORG-12962
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H11ClF3N3
Molar mass265.66 g·mol−1
3D model (JSmol)
  • C2CNCCN2c(nc1Cl)ccc1C(F)(F)F
  • 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 checkY
  • Key:QZYYPQAYSFBKPW-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Synthesis

Note that patent serves to deliver 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazine [132834-59-4], although patent is correct one: CID:9796408. Hence, ORG-12962, would need 2,6-Dichloro-3-(trifluoromethyl)pyridine [55304-75-1].

Patent:[3] Prec:[4][5]

2,3-dichloro-5-trifluoromethylpyridine [69045-84-7]

See also

References
  1. Porter RH, Benwell KR, Lamb H, Malcolm CS, Allen NH, Revell DF, Adams DR, Sheardown MJ (September 1999). "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. doi:10.1038/sj.bjp.0702751. PMC 1571597. PMID 10498829.
  2. Monck NJ, Kennett GA (2008). "5-HT2C ligands: recent progress". Progress in Medicinal Chemistry. 46: 281–390. doi:10.1016/S0079-6468(07)00006-9. ISBN 9780444530189. PMID 18381128.
  3. Patrick Carlier, Andre Monteil, & Claude Poisson, U.S. Patent 4,971,969 (1980 to Organon NV).
  4. 于俊田, CN106008330A (2016 to SHANDONG fur CO Ltd).
  5. Wanjin YU, et al. WO 2019109936 (to Zhejiang Chemical Industry Research Institute Co Ltd, Zhejiang Lantian Environmental Protection Hi Tech Co Ltd, Sinochem Lantian Co Ltd.)


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