U-50488 HCl (racemic)
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 530535

CAS#: 67197-96-0 (racemic HCl)

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


Price and Availability

Size
Price

25mg
USD 250
Size
Price

Size
Price

U-50488 HCl (racemic), purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 530535
Name: U-50488 HCl (racemic)
CAS#: 67197-96-0 (racemic HCl)
Chemical Formula: C19H27Cl3N2O
Exact Mass:
Molecular Weight: 405.788
Elemental Analysis: C, 56.24; H, 6.71; Cl, 26.21; N, 6.90; O, 3.94


Related CAS #: 67197-96-0 (racemic HCl)   114528-79-9 ((-)-U-50488 HCl)   67198-13-4 (free base)  

Synonym: U-50,488; U 50,488; U50,488; U-50488; U 50488; U50488; MCV 4133; NIH 9470; U 50488E;

IUPAC/Chemical Name: 2-(3,4-dichlorophenyl)-N-methyl-N-(-2-(pyrrolidin-1-yl)cyclohexyl)acetamide hydrochloride

InChi Key: KGMMGVIYOHGOKQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H26Cl2N2O.ClH/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;1H

SMILES Code: O=C(N(C)C1C(N2CCCC2)CCCC1)CC3=CC=C(Cl)C(Cl)=C3.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: 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. PubMed PMID: 24090794; PubMed Central PMCID: PMC4476271.

2: 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. PubMed PMID: 23222359; PubMed Central PMCID: PMC3530143.

3: 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. PubMed PMID: 19358960.

4: 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. PubMed PMID: 18929596.

5: Deuis JR, Whately E, Brust A, Inserra MC, Asvadi NH, Lewis RJ, Alewood PF, Cabot PJ, Vetter I. Activation of κ Opioid Receptors in Cutaneous Nerve Endings by Conorphin-1, a Novel Subtype-Selective Conopeptide, Does Not Mediate Peripheral Analgesia. ACS Chem Neurosci. 2015 Oct 21;6(10):1751-8. doi: 10.1021/acschemneuro.5b00113. PubMed PMID: 26225903.

6: Ambriz-Tututi M, Rocha-González HI, Castañeda-Corral G, Araiza-Saldaña CI, Caram-Salas NL, Cruz SL, Granados-Soto V. Role of opioid receptors in the reduction of formalin-induced secondary allodynia and hyperalgesia in rats. Eur J Pharmacol. 2009 Oct 1;619(1-3):25-32. doi: 10.1016/j.ejphar.2009.08.001. PubMed PMID: 19686723.

7: 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. PubMed PMID: 27590036.

8: Lasukova TV, Maslov LN, Nizkodubova SW, Gorbunov AS, Zibulnikov SY. Role of Intracellular Calcium and Cyclic Nucleotides in Realization of Cardioprotective Effects of δ(1)- and κ(1)-Opioid Receptor Agonists. Bull Exp Biol Med. 2009 Dec;148(6):877-80. PubMed PMID: 21116495.

9: 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. PubMed PMID: 11829153.

10: Wiley MD, Poveromo LB, Antapasis J, Herrera CM, Bolaños Guzmán CA. Kappa-opioid system regulates the long-lasting behavioral adaptations induced by early-life exposure to methylphenidate. Neuropsychopharmacology. 2009 Apr;34(5):1339-50. doi: 10.1038/npp.2008.188. PubMed PMID: 18923399; PubMed Central PMCID: PMC2656574.

11: Schunk E, Aigner C, Stefanova N, Wenning G, Herzog H, Schwarzer C. Kappa opioid receptor activation blocks progressive neurodegeneration after kainic acid injection. Hippocampus. 2011 Sep;21(9):1010-20. doi: 10.1002/hipo.20813. PubMed PMID: 21391243.

12: Wang Q, Sun Y, Li J, Xing W, Zhang S, Gu X, Feng N, Zhao L, Fan R, Wang Y, Yin W, Pei J. Quaternary ammonium salt of U50488H, a new κ-opioid receptor agonist, protects rat heart against ischemia/reperfusion injury. Eur J Pharmacol. 2014 Aug 15;737:177-84. doi: 10.1016/j.ejphar.2014.05.006. PubMed PMID: 24855042.

13: Nagasaka Y, Yokoyama O, Komatsu K, Ishiura Y, Nakamura Y, Namiki M. Effects of opioid subtypes on detrusor overactivity in rats with cerebral infarction. Int J Urol. 2007 Mar;14(3):226-31; discussion 232. PubMed PMID: 17430260.

14: Capasso R, Borrelli F, Zjawiony J, Kutrzeba L, Aviello G, Sarnelli G, Capasso F, Izzo AA. The hallucinogenic herb Salvia divinorum and its active ingredient salvinorin A reduce inflammation-induced hypermotility in mice. Neurogastroenterol Motil. 2008 Feb;20(2):142-8. PubMed PMID: 17931335.

15: Jang CG, Lee SY, Park Y, Ma T, Loh HH, Ho IK. Differential effects of morphine, DPDPE, and U-50488 on apomorphine-induced climbing behavior in mu-opioid receptor knockout mice. Brain Res Mol Brain Res. 2001 Oct 19;94(1-2):197-9. PubMed PMID: 11597780.

16: Bilkei-Gorzo A, Mauer D, Michel K, Zimmer A. Dynorphins regulate the strength of social memory. Neuropharmacology. 2014 Feb;77:406-13. doi: 10.1016/j.neuropharm.2013.10.023. PubMed PMID: 24184385.

17: Jones DC, Hallyburton I, Stojanovski L, Read KD, Frearson JA, Fairlamb AH. Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis. Biochem Pharmacol. 2010 Nov 15;80(10):1478-86. doi: 10.1016/j.bcp.2010.07.038. PubMed PMID: 20696141; PubMed Central PMCID: PMC3025325.

18: Buesa I, Urrutia A, Aira Z, Salgueiro M, Bilbao J, Mozas M, Aguilera L, Zimmermann M, Azkue JJ. Depression of C fibre-evoked spinal field potentials by the spinal delta opioid receptor is enhanced in the spinal nerve ligation model of neuropathic pain: involvement of the mu-subtype. Neuropharmacology. 2008 Dec;55(8):1376-82. doi: 10.1016/j.neuropharm.2008.08.029. PubMed PMID: 18775732.

19: Walker BM, Kissler JL. Dissociable effects of kappa-opioid receptor activation on impulsive phenotypes in wistar rats. Neuropsychopharmacology. 2013 Oct;38(11):2278-85. doi: 10.1038/npp.2013.129. PubMed PMID: 23689673; PubMed Central PMCID: PMC3773679.

20: Yokoyama O, Mita E, Akino H, Tanase K, Ishida H, Namiki M. Roles of opiate in lower urinary tract dysfunction associated with spinal cord injury in rats. J Urol. 2004 Feb;171(2 Pt 1):963-7. PubMed PMID: 14713862.