U-50488 free base

For research use only. Not for therapeutic Use.

  • CAT Number: I037705
  • CAS Number: 67198-13-4
  • Molecular Formula: C19H26Cl2N2O
  • Molecular Weight: 369.33
  • Purity: 98%
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U-50488 Free Base (Cat.No:I037705) is a non-peptide, kappa-opioid receptor agonist which has also been found to stimulate the release of adrenocorticotropin (ADRENOCORTICOTROPIC HORMONE) via the release of hypothalamic arginine vasopressin (ARGININE VASOPRESSIN) and CORTICOTROPIN-RELEASING HORMONE.


Catalog Number I037705
CAS Number 67198-13-4
Synonyms

U-50488 Free Base; U50488; U 50488; UM1382; UM-1382; UM 1382

Molecular Formula C19H26Cl2N2O
Purity 98%
Solubility To be determined
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name Benzeneacetamide, 3,4-dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-, trans-
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
InChIKey VQLPLYSROCPWFF-QZTJIDSGSA-N
SMILES O=C(N(C)[C@H]1[C@H](N2CCCC2)CCCC1)CC3=CC=C(Cl)C(Cl)=C3
Reference

1: Faunce KE, Banks ML. Effects of repeated kappa-opioid receptor agonist U-50488 treatment and subsequent termination on intracranial self-stimulation in male and female rats. Exp Clin Psychopharmacol. 2020 Feb;28(1):44-54. doi: 10.1037/pha0000287. PMID: 31008640.
2: Kuzeff RM, Topashka-Ancheva M, Metcheva R. Isopathic versus enantiomeric inhibition of U-50488 HCl toxicity–experimental studies. Homeopathy. 2009 Apr;98(2):83-7. doi: 10.1016/j.homp.2009.02.002. PMID: 19358960.
3: Russell SE, Rachlin AB, Smith KL, Muschamp J, Berry L, Zhao Z, Chartoff EH. Sex differences in sensitivity to the depressive-like effects of the kappa opioid receptor agonist U-50488 in rats. Biol Psychiatry. 2014 Aug 1;76(3):213-22. doi: 10.1016/j.biopsych.2013.07.042. Epub 2013 Oct 3. PMID: 24090794; PMCID: PMC4476271.
4: Mohr AL, Friscia M, Papsun D, Kacinko SL, Buzby D, Logan BK. Analysis of Novel Synthetic Opioids U-47700, U-50488 and Furanyl Fentanyl by LC-MS/MS in Postmortem Casework. J Anal Toxicol. 2016 Nov;40(9):709-717. doi: 10.1093/jat/bkw086. Epub 2016 Sep 1. PMID: 27590036.
5: Towett PK, Kanui TI, Maloiy GM, Juma F, Olongida Ole Miaron J. Activation of micro, delta or kappa opioid receptors by DAMGO, DPDPE, U-50488 or U-69593 respectively causes antinociception in the formalin test in the naked mole-rat (Heterocephalus glaber). Pharmacol Biochem Behav. 2009 Feb;91(4):566-72. doi: 10.1016/j.pbb.2008.09.011. Epub 2008 Oct 1. PMID: 18929596.
6: Hassan B, Ruiz-Velasco V. The κ-opioid receptor agonist U-50488 blocks Ca2+ channels in a voltage- and G protein-independent manner in sensory neurons. Reg Anesth Pain Med. 2013 Jan-Feb;38(1):21-7. doi: 10.1097/AAP.0b013e318274a8a1. PMID: 23222359; PMCID: PMC3530143.
7: Haji A, Takeda R. Effects of a kappa-receptor agonist U-50488 on bulbar respiratory neurons and its antagonistic action against the mu receptor-induced respiratory depression in decerebrate cats. Jpn J Pharmacol. 2001 Dec;87(4):333-7. doi: 10.1254/jjp.87.333. PMID: 11829153.
8: Tang AH, Collins RJ. Behavioral effects of a novel kappa opioid analgesic, U-50488, in rats and rhesus monkeys. Psychopharmacology (Berl). 1985;85(3):309-14. doi: 10.1007/BF00428193. PMID: 3923516.
9: Liu JJ, Sharma K, Zangrandi L, Chen C, Humphrey SJ, Chiu YT, Spetea M, Liu- Chen LY, Schwarzer C, Mann M. In vivo brain GPCR signaling elucidated by phosphoproteomics. Science. 2018 Jun 22;360(6395):eaao4927. doi: 10.1126/science.aao4927. PMID: 29930108; PMCID: PMC6527112.
10: Zhu GY, Lin FS, Wang CQ. [Effects of microiontophoretically applied U-50488 on the spontaneous discharges, of respiration related units (RRUs) in the region of nucleus ambiguus or rat]. Sheng Li Xue Bao. 1991 Apr;43(2):199-203. Chinese. PMID: 1648794.

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