8A-PDHQ

8a-Phenyldecahydroquinoline (8A-PDHQ) is a high affinity NMDA antagonist developed by a team at Parke Davis in the 1950s.[1] It is a structural analog of phencyclidine with slightly lower binding affinity than the parent compound. (-)-8a-Phenyldecahydroquinoline has an in vivo potency comparable to that of (+)-MK-801.[2][3]

8A-PDHQ
Identifiers
IUPAC name
  • 8a-phenyldecahydroquinoline
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21N
Molar mass215.340 g·mol−1
3D model (JSmol)
SMILES
  • C1([C@]23CCCC[C@H]2CCCN3)=CC=CC=C1
InChI
  • InChI=1S/C15H21N/c1-2-7-13(8-3-1)15-11-5-4-9-14(15)10-6-12-16-15/h1-3,7-8,14,16H,4-6,9-12H2 Y
  • Key:QEXADSRMRUUCQJ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

References
  1. US Patent 3035059
  2. Chen C, Kozikowski AP, Wood PL, Reynolds IJ, Ball RG, Pang YP (May 1992). "Synthesis and biological activity of 8a-phenyldecahydroquinolines as probes of PCP's binding conformation. A new PCP-like compound with increased in vivo potency". Journal of Medicinal Chemistry. 35 (9): 1634–8. doi:10.1021/jm00087a020. PMID 1315871.
  3. Elhallaoui M, Laguerre M, Carpy A, Ouazzani FC (February 2002). "Molecular modeling of noncompetitive antagonists of the NMDA receptor: proposal of a pharmacophore and a description of the interaction mode". Journal of Molecular Modeling. 8 (2): 65–72. doi:10.1007/s00894-001-0067-4. PMID 12032600.
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