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U-50488

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Chemical compound

Pharmaceutical compound

U-50488
Identifiers


IUPAC name 2-(3,4-dichlorophenyl)-N-methyl-N-[(1R,2R)-2-pyrrolidin-1-ylcyclohexyl]acetamide
CAS Number	67198-13-4^Y
PubChemCID	3036289
IUPHAR/BPS	1652
ChemSpider	2300345^N
UNII	39K8JHE8XN
ChEBI	CHEBI:73358^N
ChEMBL	ChEMBL441765^N
CompTox Dashboard(EPA)	DTXSID60953023
Chemical and physical data
Formula	C₁₉H₂₆Cl₂N₂O
Molar mass	369.33 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN([C@@H]1CCCC[C@H]1N2CCCC2)C(=O)CC3=CC(=C(C=C3)Cl)Cl
InChI InChI=1S/C19H26Cl2N2O/c1-22(19(24)13-14-8-9-15(20)16(21)12-14)17-6-2-3-7-18(17)23-10-4-5-11-23/h8-9,12,17-18H,2-7,10-11,13H2,1H3/t17-,18-/m1/s1^N Key:VQLPLYSROCPWFF-QZTJIDSGSA-N^N
^NY (what is this?) (verify)

U-50488 is a drug which acts as a highly selectiveκ-opioid agonist, but without anyμ-opioid antagonist effects.^[1] It hasanalgesic,diuretic andantitussive effects,^[2] and reverses the memory impairment produced byanticholinergic drugs.^[3] U-50488 was one of the first selective kappa agonists invented and research on its derivatives has led to the development of a large family of related compounds.^[4]^[5] This compound has never received FDA approval and there are no reported human cases in the literature involving an U-50488 overdose.^[6]

References

[edit]

^Von Voigtlander PF, Lewis RA (1982). "U-50,488, a selective kappa opioid agonist: comparison to other reputed kappa agonists".Progress in Neuro-Psychopharmacology & Biological Psychiatry.6 (4–6):467–70.doi:10.1016/S0278-5846(82)80130-9.PMID 6298890.S2CID 37011292.
^Kamei J (1996). "Role of opioidergic and serotonergic mechanisms in cough and antitussives".Pulmonary Pharmacology.9 (5–6):349–56.doi:10.1006/pulp.1996.0046.PMID 9232674.
^Hiramatsu M, Kameyama T (September 1998). "Roles of kappa-opioid receptor agonists in learning and memory impairment in animal models".Methods and Findings in Experimental and Clinical Pharmacology.20 (7):595–9.doi:10.1358/mf.1998.20.7.485724.PMID 9819804.
^Szmuszkovicz J (1999). "U-50,488 and the к receptor: A personalized account covering the period 1973 to 1990".Progress in Drug Research. Vol. 52. pp. 167–95.doi:10.1007/978-3-0348-8730-4_4.ISBN 978-3-0348-9746-4.PMID 10396128.
^Szmuszkovicz J (1999). "U-50,488 and the kappa receptor. Part II: 1991-1998".Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques.53:1–51.PMID 10616295.
^Amin ZM, Rambaran KA, Fleming SW, Cho K, Chacko L, Alzghari SK (December 2017)."Addressing Hazards from Unscheduled Novel Psychoactive Substances as Research Chemicals: The Case of U-50488".Cureus.9 (12) e1914.doi:10.7759/cureus.1914.PMC 5800751.PMID 29441248.