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PD-137889

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PD-137889
Names
IUPAC name (4aR)-N-Methyl-1,2,3,4,9,9a-hexahydro-4aH-fluoren-4a-amine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H19N/c1-15-14-9-5-4-7-12(14)10-11-6-2-3-8-13(11)14/h2-3,6,8,12,15H,4-5,7,9-10H2,1H3Key: KQLIVVYSTDBTMZ-UHFFFAOYSA-N
SMILES
  • c12c(cccc1)C3(NC)CCCCC3C2
Properties
Chemical formula C14H19N
Molar mass 201.313 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

PD-137889 (N-methylhexahydrofluorenamine) is a chemical compound that is active as an NMDA receptor antagonist in the central nervous system at roughly 30 times the potency of the "flagship" of its class, ketamine, and substitutes for phencyclidine in animal studies. Ki TCP binding = 27 nM versus ketamine's Ki = 860 nM.


See also

References

  1. Hays, Sheryl J.; Novak, Perry M.; Ortwine, Daniel F.; Bigge, Christopher F.; Colbry, Norman L.; Johnson, Graham; Lescosky, Leonard J.; Malone, Thomas C.; Michael, Andre (1993). "Synthesis and pharmacological evaluation of hexahydrofluorenamines as noncompetitive antagonists at the N-methyl-D-aspartate receptor". J Med Chem. 36 (6): 654–70. doi:10.1021/jm00058a002. PMID 8459395.
  2. Nicholson, Katherine L.; Balster, Robert L. (2003). "Evaluation of the phencyclidine-like discriminative stimulus effects of novel NMDA channel blockers in rats". Psychopharmacology. 170 (2): 215–224. doi:10.1007/s00213-003-1527-6. PMID 2851738. S2CID 30803162.
  3. Bigge, Christopher F. (1993). "Structural requirements for the development of potent n-methyl-d-aspartic acid (NMDA) receptor antagonists". Biochemical Pharmacology. 45 (8): 1547–1561. doi:10.1016/0006-2952(93)90294-7. PMID 7683469.
  4. Bigge, Christopher F.; Malone, Thomas C. (1993). "Overview: Agonists, Antagonists and Modulators of the N-methyl-D-aspartic acid (NMDA) and α-amino-3-hydroxy-5-methyl-4-isoxazolepropanoic acid (AMPA) Subtypes of Glutamate Receptors". Current Opinion on Therapeutic Patents. 3 (7): 951–989. doi:10.1517/13543776.3.7.951.
  5. Polycyclic amine derivatives useful as cerebrovascular agents Archived 2018-02-03 at the Wayback Machine United States Patent; Coughenour, et al. Family ID: 22686445 Appl. #07/186,834
  1. N-piperidine
Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor


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