LY-235959

LY-235959 is a competitive antagonist at the NMDA receptor.[1] It has analgesic and neuroprotective effects and causes hypothermia in animal models,[2] as well as reducing the development of tolerance to morphine and altering the reinforcing effects of cocaine.[3][4][5][6][7]

LY-235959
Identifiers
IUPAC name
  • (3S,4aR,6S,8aR)-6-(phosphonomethyl)-1,2,3,4,4a,5,6,7,8, 8a-decahydroisoquinoline-3-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H20NO5P
Molar mass277.257 g·mol−1
3D model (JSmol)
SMILES
  • [H][C@]12[C@](CC[C@H](CP(O)(O)=O)C2)([H])CN[C@H](C(O)=O)C1
InChI
  • InChI=1S/C11H20NO5P/c13-11(14)10-4-9-3-7(6-18(15,16)17)1-2-8(9)5-12-10/h7-10,12H,1-6H2,(H,13,14)(H2,15,16,17)/t7-,8-,9+,10-/m0/s1
  • Key:STIRHCNEGQQBOY-QEYWKRMJSA-N

References
  1. Allen RM, Dykstra LA (July 2001). "N-methyl-D-aspartate receptor antagonists potentiate the antinociceptive effects of morphine in squirrel monkeys". The Journal of Pharmacology and Experimental Therapeutics. 298 (1): 288–97. PMID 11408554.
  2. Rawls SM, Cowan A, Tallarida RJ, Geller EB, Adler MW (October 2002). "N-methyl-D-aspartate antagonists and WIN 55212-2 [4,5-dihydro-2-methyl-4(4-morpholinylmethyl)-1-(1-naphthalenyl-carbonyl)-6H-pyrrolo[3,2,1-i,j]quinolin-6-one], a cannabinoid agonist, interact to produce synergistic hypothermia". The Journal of Pharmacology and Experimental Therapeutics. 303 (1): 395–402. doi:10.1124/jpet.102.037473. PMID 12235276.
  3. Allen RM, Carelli RM, Dykstra LA, Suchey TL, Everett CV (October 2005). "Effects of the competitive N-methyl-D-aspartate receptor antagonist, LY235959 [(-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid], on responding for cocaine under both fixed and progressive ratio schedules of reinforcement". The Journal of Pharmacology and Experimental Therapeutics. 315 (1): 449–57. doi:10.1124/jpet.105.086355. PMID 16024734.
  4. Allen RM, Dykstra LA, Carelli RM (April 2007). "Continuous exposure to the competitive N-methyl-D: -aspartate receptor antagonist, LY235959, facilitates escalation of cocaine consumption in Sprague-Dawley rats". Psychopharmacology. 191 (2): 341–51. doi:10.1007/s00213-006-0661-3. PMID 17225167.
  5. Fischer BD, Ward SJ, Henry FE, Dykstra LA (February 2010). "Attenuation of morphine antinociceptive tolerance by a CB(1) receptor agonist and an NMDA receptor antagonist: Interactive effects". Neuropharmacology. 58 (2): 544–50. doi:10.1016/j.neuropharm.2009.08.005. PMC 2813317. PMID 19699755.
  6. Dykstra LA, Fischer BD, Balter RE, Henry FE, Schmidt KT, Miller LL (September 2011). "Opioid antinociception, tolerance and dependence: interactions with the N-methyl-D-aspartate system in mice". Behavioural Pharmacology. 22 (5–6): 540–7. doi:10.1097/FBP.0b013e328348ed08. PMC 3155647. PMID 21712708.
  7. Bicca MA, Figueiredo CP, Piermartiri TC, Meotti FC, Bouzon ZL, Tasca CI, et al. (September 2011). "The selective and competitive N-methyl-D-aspartate receptor antagonist, (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid, prevents synaptic toxicity induced by amyloid-β in mice". Neuroscience. 192: 631–41. doi:10.1016/j.neuroscience.2011.06.038. PMID 21756976.
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