PD-137889

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,[1] and substitutes for phencyclidine in animal studies.[2][3][4] Ki [3H]TCP[lower-alpha 1] binding = 27 nM versus ketamine's Ki = 860 nM.[5]

PD-137889
Names
IUPAC name
(4aR)-N-Methyl-1,2,3,4,9,9a-hexahydro-4aH-fluoren-4a-amine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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,4-5,7,9-10H2,1H3
    Key: KQLIVVYSTDBTMZ-UHFFFAOYSA-N
  • c12c(cccc1)C3(NC)CCCCC3C2
Properties
C14H19N
Molar mass 201.313 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references


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 United States Patent; Coughenour, et al. Family ID: 22686445 Appl. #07/186,834
  1. [3H]N-[1-(2-thienyl)cyclohex-yl]piperidine


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