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{{Short description|Chemical compound}}
⚫ {{Drugbox| verifiedrevid = 398935365
{{cs1 config|name-list-style=vanc}}
|
{{Drugbox
⚫ |IUPAC_name = 8a-phenyldecahydroquinoline
| Verifiedfields = changed
| Watchedfields = changed
⚫ | verifiedrevid = 477227464
⚫ | IUPAC_name = 8a-phenyldecahydroquinoline
| image = Phenyldecahydroquinoline.svg | image = Phenyldecahydroquinoline.svg
| width= 150 | width = 150

<!--Clinical data-->
| tradename =
⚫ | routes_of_administration =

<!--Pharmacokinetic data-->
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
⚫ | CAS_number = 131556-11-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8GBT78N4EC
⚫ | PubChem = 131397
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 116144 | ChemSpiderID = 116144

| InChI = 1/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
<!--Chemical data-->
| smiles = c1ccccc1C32NCCCC2CCCC3
⚫ | C=15 | H=21 | N=1
| InChIKey = QEXADSRMRUUCQJ-UHFFFAOYAG
| smiles = C1(23CCCC2CCCN3)=CC=CC=C1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QEXADSRMRUUCQJ-UHFFFAOYSA-N | StdInChIKey = QEXADSRMRUUCQJ-UHFFFAOYSA-N
⚫ | CAS_number= 131556-11-1
| ATC_prefix=
| ATC_suffix=
⚫ | PubChem= 131397
| DrugBank=
⚫ | C=15 | H=21 | N=1
| molecular_weight = 215.3339 g/mol
| bioavailability=
⚫ | metabolism =
⚫ | elimination_half-life=
⚫ | excretion =
| pregnancy_category =
| legal_status =
⚫ | routes_of_administration=
}} }}


'''8a-Phenyldecahydroquinoline''' ('''8A-PDHQ''') is a high affinity ]. It is a structural analog of ] with slightly lower binding affinity than the parent compound. (-)-8a-Phenyldecahydroquinoline has an in vivo potency comparable to that of (+)-MK-801.<ref>{{cite journal|author=Chen C, Kozikowski AP, Wood PL, Reynolds IJ, Ball RG, Pang YP |title=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=J Med Chem |year=1992| volume=35 |issue=9|pmid=1315871|pages=1634–8|doi=10.1021/jm00087a020}}</ref><ref>{{cite journal| author=Elhallaoui M, Laguerre M, Carpy A, Ouazzani FC |title=Molecular modeling of noncompetitive antagonists of the NMDA receptor: proposal of a pharmacophore and a description of the interaction mode |journal=J Mol Model |year=2002 |volume= 8 |issue=2| pmid=12032600 |pages=65–72| doi=10.1007/s00894-001-0067-4}}</ref> '''8a-Phenyldecahydroquinoline''' ('''8A-PDHQ''') is a high affinity ] developed by a team at Parke Davis in the 1950s.<ref>US Patent 3035059</ref> It is a structural analog of ] with slightly lower binding affinity than the parent compound. (−)-8a-Phenyldecahydroquinoline has an in vivo potency comparable to that of (+)-].<ref>{{cite journal | vauthors = Chen C, Kozikowski AP, Wood PL, Reynolds IJ, Ball RG, Pang YP | title = 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 = Journal of Medicinal Chemistry | volume = 35 | issue = 9 | pages = 1634–8 | date = May 1992 | pmid = 1315871 | doi = 10.1021/jm00087a020 }}</ref><ref>{{cite journal | vauthors = Elhallaoui M, Laguerre M, Carpy A, Ouazzani FC | title = Molecular modeling of noncompetitive antagonists of the NMDA receptor: proposal of a pharmacophore and a description of the interaction mode | journal = Journal of Molecular Modeling | volume = 8 | issue = 2 | pages = 65–72 | date = February 2002 | pmid = 12032600 | doi = 10.1007/s00894-001-0067-4 | s2cid = 34882820 }}</ref>


== References == == References ==
{{reflist}} {{reflist}}


{{Hallucinogens}}

{{Ionotropic glutamate receptor modulators}}

{{Dissociative_hallucinogens}}
{{Glutamate_receptor_ligands}}


{{DEFAULTSORT:Phenyldecahydroquinoline, 8a-}} {{DEFAULTSORT:Phenyldecahydroquinoline, 8a-}}

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Latest revision as of 19:39, 4 February 2024

Chemical compound

Pharmaceutical compound
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
3D model (JSmol)
SMILES
  • C1(23CCCC2CCCN3)=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
  (what is this?)  (verify)

8a-Phenyldecahydroquinoline (8A-PDHQ) is a high affinity NMDA antagonist developed by a team at Parke Davis in the 1950s. 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.

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. S2CID 34882820.
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