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G133 Sigma

GR 89696 fumarate salt

solid

Synonym: 4-[(3,4-Dichlorophenyl)acetyl]-3-(1-pyrrolidinylmethyl)-1-piperazinecarboxylic acid methyl ester fumarate salt

  • CAS Number 126766-32-3

  • Empirical Formula (Hill Notation) C19H25Cl2N3O3 · C4H4O4

  • Molecular Weight 530.40

  •  MDL number MFCD00274044

  •  PubChem Substance ID 24278038

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Description

Biochem/physiol Actions

Selective κ2 opioid receptor agonist.

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Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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GR89,696 is a κ2 opioid receptor agonist and a κ1 opioid receptor antagonist in the guinea pig hippocampus. Caudle, R.M., et al. J. Pharmacol. Exp. Ther. 283, 1342-1349, (1997)

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Neuroprotective actions of GR 89696 a highly potent and selective κ-opioid recetptor agonist. Birch, et al. Br. J. Pharmacol. 103, 1819-1823, (1991)

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GR94839 a κ opioid agonist with limited access to the central nervous system has antinociceptive activity. Rogers, H. Br. J. Pharmacol. 106, 783-789, (1992)

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Determination of in vivo Bmax and Kd for 11C-GR103545, an agonist PET tracer for κ-opioid receptors: a study in nonhuman primates. Tomasi G, Nabulsi N, Zheng MQ, et al. J. Nucl. Med. 54(4), 600-8, (2013)

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[11C]GR103545: novel one-pot radiosynthesis with high specific activity. Nabulsi NB, Zheng MQ, Ropchan J, et al. Nucl. Med. Biol. 38(2), 215-21, (2011)

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Effects of atypical kappa-opioid receptor agonists on intrathecal morphine-induced itch and analgesia in primates. Ko MC and Husbands SM J. Pharmacol. Exp. Ther. 328(1), 193-200, (2009)

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GR89,696: a potent kappa-opioid agonist with subtype selectivity in rhesus monkeys. Butelman ER, Ko MC, Traynor JR, et al. J. Pharmacol. Exp. Ther. 298(3), 1049-59, (2001)

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Evaluation of the kappa-opioid receptor-selective tracer [(11)C]GR103545 in awake rhesus macaques. Schoultz BW, Hjornevik T, Willoch F, et al. Eur. J. Nucl. Med. Mol. Imaging 37(6), 1174-80, (2010)

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Induction of bladder sphincter dyssynergia by kappa-2 opioid receptor agonists in the female rat. Gu B, Fraser MO, Thor KB, et al. J. Urol. 171(1), 472-7, (2004)

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Pharmacological characterization of 2-methyl-N-((2'-(pyrrolidin-1-ylsulfonyl)biphenyl-4-yl)methyl)propan-1-amine (PF-04455242), a high-affinity antagonist selective for κ-opioid receptors. Grimwood, S., et al. J. Pharmacol. Exp. Ther. 339, 555-566, (2011)

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[Role of kappa-opioid receptors in the regulation of cardiac resistance to arrhythmogenic effects of ischemia and reperfusion]. Lishmanov AIu, Lasukova TV, Maslov LN, et al. Ross. Fiziol. Zh. Im. I. M. Sechenova 92(12), 1419-28, (2006)

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Methylated analogues of methyl (R)-4-(3,4-dichlorophenylacetyl)- 3-(pyrrolidin-1-ylmethyl)piperazine-1-carboxylate (GR-89,696) as highly potent kappa-receptor agonists: stereoselective synthesis, opioid-receptor affinity, receptor selectivity, and functional studies. Soukara S, Maier CA, Predoiu U, et al. J. Med. Chem. 44(17), 2814-26, (2001)

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Opioid regulation of spinal cord plasticity: evidence the kappa-2 opioid receptor agonist GR89696 inhibits learning within the rat spinal cord. Washburn SN, Maultsby ML, Puga DA, et al. Neurobiol. Learn. Mem. 89(1), 1-16, (2008)

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11C-GR103545, a radiotracer for imaging kappa-opioid receptors in vivo with PET: synthesis and evaluation in baboons. Talbot PS, Narendran R, Butelman ER, et al. J. Nucl. Med. 46(3), 484-94, (2005)

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Functional evidence for multiple receptor activation by kappa-ligands in the inhibition of spinal nociceptive reflexes in the rat. Herrero JF and Headley PM Br. J. Pharmacol. 110(1), 303-9, (1993)

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The kappa opioid agonist GR89,696 blocks hyperalgesia and allodynia in rat models of peripheral neuritis and neuropathy. Eliav E, Herzberg U, and Caudle RM Pain 79(2-3), 255-64, (1999)

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[(11)C]-GR89696, a potent kappa opiate receptor radioligand; in vivo binding of the R and S enantiomers. Ravert HT, Scheffel U, Mathews WB, et al. Nucl. Med. Biol. 29(1), 47-53, (2002)

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The intrathecally administered kappa-2 opioid agonist GR89696 and interleukin-10 attenuate bone cancer-induced pain through synergistic interaction. Kim WM, Jeong CW, Lee SH, et al. Anesth. Analg. 113(4), 934-40, (2011)

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Synthesis and stereoselective kappa-receptor binding of methylated analogues of GR-89.696. Röhr C, Soukara S, and Wünsch B Eur. J. Med. Chem. 36(2), 211-4, (2001)

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[11C]-methyl 4-[(3,4-dichlorophenyl)acetyl]-3-[(1-pyrrolidinyl)-methyl]-1- piperazinecarboxylate ([11C]GR89696): synthesis and in vivo binding to kappa opiate receptors. Ravert HT, Mathews WB, Musachio JL, et al. Nucl. Med. Biol. 26(7), 737-41, (1999)

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Putative kappa-2 opioid agonists are antihyperalgesic in a rat model of inflammation. Ho J, Mannes AJ, Dubner R, et al. J. Pharmacol. Exp. Ther. 281(1), 136-41, (1997)

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A potent new class of kappa-receptor agonist: 4-substituted 1-(arylacetyl)-2-[(dialkylamino)methyl]piperazines. Naylor A, Judd DB, Lloyd JE, et al. J. Med. Chem. 36(15), 2075-83, (1993)

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NK(3) receptors in the feline nucleus tractus solitarius are not involved with the muscle pressor response. Fry B, Reifsteck A, Hoover DB, et al. Neuropeptides 35(3-4), 154-61, (2001)

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Sensory nerve-mediated relaxation of guinea-pig isolated pulmonary artery: prejunctional modulation by alpha 2-adrenoceptor agonists but not sumatriptan. Butler A, Worton SP, O'Shaughnessy CT, et al. Br. J. Pharmacol. 109(1), 126-30, (1993)

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Effects of GR-89696 and the novel peripherally selective OP2 agonists, EMD-61569 and EMD-61747, against focal cerebral ischemia in the rat. Barber A, Bender HM, Gottschlich R, et al. Methods Find. Exp. Clin. Pharmacol. 21(2), 105-13, (1999)

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Myocardial resistance to ischemic and reperfusion injuries under conditions of chronic administration of opioid receptor agonists and antagonists. Lishmanov YB, Stakheev DL, Krylatov AV, et al. Bull. Exp. Biol. Med. 145(6), 696-9, (2008)

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