U-50488

U-50488 is a drug which acts as a highly selective κ-opioid agonist, but without any μ-opioid antagonist effects.[1] It has analgesic, diuretic and antitussive effects,[2] and reverses the memory impairment produced by anticholinergic 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]

U-50488
Identifiers
IUPAC name
  • 2-(3,4-dichlorophenyl)-N-methyl-N-[(1R,2R)-2-pyrrolidin-1-ylcyclohexyl]acetamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H26Cl2N2O
Molar mass369.33 g·mol−1
3D model (JSmol)
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)

See also

References
  1. 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.
  2. 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.
  3. 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.
  4. Szmuszkovicz J (1999). "U-50,488 and the kappa receptor: a personalized account covering the period 1973 to 1990". Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progrès des Recherches Pharmaceutiques. 52: 167–95. doi:10.1007/978-3-0348-8730-4_4. PMID 10396128.
  5. Szmuszkovicz J (1999). "U-50,488 and the kappa receptor. Part II: 1991-1998". Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progrès des Recherches Pharmaceutiques. 53: 1–51. PMID 10616295.
  6. 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.


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