8A-PDHQ

8A-PDHQ

Systematic (IUPAC) name
8a-phenyldecahydroquinoline
Identifiers
CAS Number	131556-11-1
PubChem	CID 131397
ChemSpider	116144
Chemical data
Formula	C15H21N
Molar mass	215.3339 g/mol
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 Key:QEXADSRMRUUCQJ-UHFFFAOYSA-N
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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]

References

1. US Patent 3035059
2. Chen C, Kozikowski AP, Wood PL, Reynolds IJ, Ball RG, Pang YP (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 (2002). "Molecular modeling of noncompetitive antagonists of the NMDA receptor: proposal of a pharmacophore and a description of the interaction mode". J Mol Model 8 (2): 65–72. doi:10.1007/s00894-001-0067-4. PMID 12032600.