GR-89696

GR-89696
Identifiers
	IUPAC name methyl 4-[2-(3,4-dichlorophenyl)acetyl]-3-(pyrrolidin-1-ylmethyl)piperazine-1-carboxylate;
CAS Number	126766-32-3 ;
PubChem CID	3505;
IUPHAR/BPS	1649;
ChemSpider	3385;
UNII	YDF52K5SDR;
ChEMBL	ChEMBL277863 ;
PDB ligand	U9I (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID50875164 ;
Chemical and physical data
Formula	C19H25Cl2N3O3
Molar mass	414.33 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1Cl)CC(=O)N2CCN(C(=O)OC)CC2CN3CCCC3;
	InChI InChI=1S/C19H25Cl2N3O3/c1-27-19(26)23-8-9-24(15(13-23)12-22-6-2-3-7-22)18(25)11-14-4-5-16(20)17(21)10-14/h4-5,10,15H,2-3,6-9,11-13H2,1H3; Key:HJUAKZYKCANOOZ-UHFFFAOYSA-N;
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GR-89696 is a drug which acts as a highly selective κ-opioid agonist.^[1] It has been studied in various animal species, and has been described as selective for the κ₂ subtype.^[2]^[3]^[4] Recent studies have suggested that GR-89696 and related κ₂-selective agonists may be useful for preventing the itching which is a common side effect of conventional opioid analgesic drugs, without the additional side effects of non-selective kappa agonists.^[5] The structure bound to the κ-opioid receptor has been reported.^[6]

References

^ Naylor A, Judd DB, Lloyd JE, Scopes DI, Hayes AG, Birch PJ (July 1993). "A potent new class of kappa-receptor agonist: 4-substituted 1-(arylacetyl)-2-[(dialkylamino)methyl]piperazines". Journal of Medicinal Chemistry. 36 (15): 2075–2083. doi:10.1021/jm00067a004. PMID 8393489.
^ Herrero JF, Headley PM (September 1993). "Functional evidence for multiple receptor activation by kappa-ligands in the inhibition of spinal nociceptive reflexes in the rat". British Journal of Pharmacology. 110 (1): 303–309. doi:10.1111/j.1476-5381.1993.tb13809.x. PMC 2176008. PMID 8220893.
^ Ho J, Mannes AJ, Dubner R, Caudle RM (April 1997). "Putative kappa-2 opioid agonists are antihyperalgesic in a rat model of inflammation". The Journal of Pharmacology and Experimental Therapeutics. 281 (1): 136–141. PMID 9103490.
^ Butelman ER, Ko MC, Traynor JR, Vivian JA, Kreek MJ, Woods JH (September 2001). "GR89,696: a potent kappa-opioid agonist with subtype selectivity in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics. 298 (3): 1049–1059. PMID 11504802.
^ Ko MC, Husbands SM (January 2009). "Effects of atypical kappa-opioid receptor agonists on intrathecal morphine-induced itch and analgesia in primates". The Journal of Pharmacology and Experimental Therapeutics. 328 (1): 193–200. doi:10.1124/jpet.108.143925. PMC 2719014. PMID 18842704.
^ Han J, Zhang J, Nazarova AL, Bernhard SM, Krumm BE, Zhao L, et al. (May 2023). "Ligand and G-protein selectivity in the κ-opioid receptor". Nature. 617 (7960): 417–425. Bibcode:2023Natur.617..417H. doi:10.1038/s41586-023-06030-7. PMC 10172140. PMID 37138078.

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[pmid8393489-1] Naylor A, Judd DB, Lloyd JE, Scopes DI, Hayes AG, Birch PJ (July 1993). "A potent new class of kappa-receptor agonist: 4-substituted 1-(arylacetyl)-2-[(dialkylamino)methyl]piperazines". Journal of Medicinal Chemistry. 36 (15): 2075–2083. doi:10.1021/jm00067a004. PMID 8393489.

[pmid8220893-2] Herrero JF, Headley PM (September 1993). "Functional evidence for multiple receptor activation by kappa-ligands in the inhibition of spinal nociceptive reflexes in the rat". British Journal of Pharmacology. 110 (1): 303–309. doi:10.1111/j.1476-5381.1993.tb13809.x. PMC 2176008. PMID 8220893.

[pmid9103490-3] Ho J, Mannes AJ, Dubner R, Caudle RM (April 1997). "Putative kappa-2 opioid agonists are antihyperalgesic in a rat model of inflammation". The Journal of Pharmacology and Experimental Therapeutics. 281 (1): 136–141. PMID 9103490.

[pmid11504802-4] Butelman ER, Ko MC, Traynor JR, Vivian JA, Kreek MJ, Woods JH (September 2001). "GR89,696: a potent kappa-opioid agonist with subtype selectivity in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics. 298 (3): 1049–1059. PMID 11504802.

[pmid18842704-5] Ko MC, Husbands SM (January 2009). "Effects of atypical kappa-opioid receptor agonists on intrathecal morphine-induced itch and analgesia in primates". The Journal of Pharmacology and Experimental Therapeutics. 328 (1): 193–200. doi:10.1124/jpet.108.143925. PMC 2719014. PMID 18842704.

[6] Han J, Zhang J, Nazarova AL, Bernhard SM, Krumm BE, Zhao L, et al. (May 2023). "Ligand and G-protein selectivity in the κ-opioid receptor". Nature. 617 (7960): 417–425. Bibcode:2023Natur.617..417H. doi:10.1038/s41586-023-06030-7. PMC 10172140. PMID 37138078.

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Identifiers


IUPAC name methyl 4-[2-(3,4-dichlorophenyl)acetyl]-3-(pyrrolidin-1-ylmethyl)piperazine-1-carboxylate
CAS Number	126766-32-3^Y
PubChem CID	3505
IUPHAR/BPS	1649
ChemSpider	3385
UNII	YDF52K5SDR
ChEMBL	ChEMBL277863^N
PDB ligand	U9I (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID50875164
Chemical and physical data
Formula	C₁₉H₂₅Cl₂N₃O₃
Molar mass	414.33 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1Cl)CC(=O)N2CCN(C(=O)OC)CC2CN3CCCC3
InChI InChI=1S/C19H25Cl2N3O3/c1-27-19(26)23-8-9-24(15(13-23)12-22-6-2-3-7-22)18(25)11-14-4-5-16(20)17(21)10-14/h4-5,10,15H,2-3,6-9,11-13H2,1H3 Key:HJUAKZYKCANOOZ-UHFFFAOYSA-N
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