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'''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]],<ref>{{cite journal|pmid=8459395|title=Synthesis and pharmacological evaluation of hexahydrofluorenamines as noncompetitive antagonists at the N-methyl-D-aspartate receptor|journal=J Med Chem|year=1993|volume=36|issue=6|pages=654–70|doi=10.1021/jm00058a002}}</ref> and substitutes for [[phencyclidine]] in animal studies.<ref>Nicholson KL, Balster RL. Evaluation of the phencyclidine-like discriminative stimulus effects of novel NMDA channel blockers in rats. ''Psychopharmacology (Berl)''. 2003 Nov;170(2):215-24. {{PMID|12851738}} doi: 10.1007/s00213-003-1527-6</ref><ref>Bigge CF. Structural requirements for the development of potent N-methyl-D-aspartic acid (NMDA) receptor antagonists. ''Biochemical Pharmacology'' 1993; 45(8):1547–1561. doi:10.1016/0006-2952(93)90294-7</ref><ref>Bigge CF, Malone TC. 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'' 1993; 3(7):951-989. doi: 10.1517/13543776.3.7.951</ref> It has a putative half-life of over ten hours. K''<sub>i</sub>'' [<sup>3</sup>H]TCP{{efn|[<sup>3</sup>H]N-[1-(2-thienyl)cyclohex-yl]piperidine}} binding = 27&nbsp;[[nanomolar|nM]] versus ketamine's K''<sub>i</sub>'' = 860&nbsp;nM.<ref>[http://patft.uspto.gov/netacgi/nph-Parser?d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=4837226.PN.&OS=PN/4837226&RS=PN/4837226 Polycyclic amine derivatives useful as cerebrovascular agents] United States Patent; Coughenour, et al. Family ID: 22686445 Appl. #07/186,834</ref>
'''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]],<ref>{{cite journal | pmid=8459395|title=Synthesis and pharmacological evaluation of hexahydrofluorenamines as noncompetitive antagonists at the N-methyl-D-aspartate receptor | journal=J Med Chem | year=1993 | volume=36 | issue=6 | pages=654–70 | doi=10.1021/jm00058a002}}</ref> and substitutes for [[phencyclidine]] in animal studies.<ref>{{cite journal | pmid = 2851738 | doi = 10.1007/s00213-003-1527-6}}</ref><ref>{{cite journal |doi = 10.1016/0006-2952(93)90294-7}}</ref><ref>{{cite journal |doi = 10.1517/13543776.3.7.951 }}</ref> It has a putative half-life of over ten hours. K''<sub>i</sub>'' [<sup>3</sup>H]TCP{{efn|[<sup>3</sup>H]N-[1-(2-thienyl)cyclohex-yl]piperidine}} binding = 27&nbsp;[[nanomolar|nM]] versus ketamine's K''<sub>i</sub>'' = 860&nbsp;nM.<ref>[http://patft.uspto.gov/netacgi/nph-Parser?d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=4837226.PN.&OS=PN/4837226&RS=PN/4837226 Polycyclic amine derivatives useful as cerebrovascular agents] United States Patent; Coughenour, et al. Family ID: 22686445 Appl. #07/186,834</ref>


==See also==
==See also==

Revision as of 11:57, 24 March 2019

PD-137889
Names
IUPAC name
(4aR)-N-Methyl-1,2,3,4,9,9a-hexahydro-4aH-fluoren-4a-amine
Identifiers
3D model (JSmol)
ChemSpider
  • 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).

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] It has a putative half-life of over ten hours. Ki [3H]TCP[a] binding = 27 nM versus ketamine's Ki = 860 nM.[5]

See also

References

  1. ^ "Synthesis and pharmacological evaluation of hexahydrofluorenamines as noncompetitive antagonists at the N-methyl-D-aspartate receptor". J Med Chem. 36 (6): 654–70. 1993. doi:10.1021/jm00058a002. PMID 8459395.
  2. ^ . doi:10.1007/s00213-003-1527-6. PMID 2851738. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  3. ^ . doi:10.1016/0006-2952(93)90294-7. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  4. ^ . doi:10.1517/13543776.3.7.951. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  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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