ORG-12962

From Wikipedia, the free encyclopedia
ORG-12962
Org12962 structure.png
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)

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]

Synthesis[edit]

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[edit]

References[edit]

  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.)