U-50488 HCl (racemic) | CAS#67197-96-0 | 114528-81-3 | 67198-13-4 | k-opioid agonist

MedKoo Cat#: 530535 | Name: U-50488 HCl (racemic)

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Description:

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

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.

Chemical Structure

U-50488 HCl (racemic)

CAS#67197-96-0 (racemic HCl)

Theoretical Analysis

MedKoo Cat#: 530535

Name: U-50488 HCl (racemic)

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

Chemical Formula: C19H27Cl3N2O

Exact Mass: 0.0000

Molecular Weight: 405.79

Elemental Analysis: C, 56.24; H, 6.71; Cl, 26.21; N, 6.90; O, 3.94

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 750.00	Ready to ship

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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

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).

HS Tariff Code

2934.99.9001

More Info

Certificate of Analysis

View CoA: current batch, Lot#A23M03C09

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 405.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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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. 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