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	67198-13-4^Y
PubChem CID	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)

See also

• U-47700
• U-69,593

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.
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. Progres Des Recherches Pharmaceutiques. 52: 167–95. PMID 10396128.
5. 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.
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.