U-69593
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MedKoo CAT#: 527820

CAS#: 96744-75-1

Description: U-69593 is a selective kappa opioid receptor agonist.


Price and Availability

Size Price Shipping out time Quantity
5mg USD 325 2 Weeks
25mg USD 900 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-09-28. Prices are subject to change without notice.

U-69593 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

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Theoretical Analysis

MedKoo Cat#: 527820
Name: U-69593
CAS#: 96744-75-1
Chemical Formula: C22H32N2O2
Exact Mass: 356.2464
Molecular Weight: 356.51
Elemental Analysis: C, 74.12; H, 9.05; N, 7.86; O, 8.98


Synonym: U069593; U 69593; U-69593

IUPAC/Chemical Name: (+)-N-methyl-2-phenyl-N-[(5R,7S,8S)-7-pyrrolidin-1-yl-1-oxaspiro[4.5]decan-8-yl]acetamide

InChi Key: PGZRDDYTKFZSFR-ONTIZHBOSA-N

InChi Code: InChI=1S/C22H32N2O2/c1-23(21(25)16-18-8-3-2-4-9-18)19-10-12-22(11-7-15-26-22)17-20(19)24-13-5-6-14-24/h2-4,8-9,19-20H,5-7,10-17H2,1H3/t19-,20-,22-/m0/s1

SMILES Code: O=C(N(C)[C@@H](CC1)[C@@H](N2CCCC2)C[C@@]31CCCO3)CC4=CC=CC=C4


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).

HS Tariff Code:
2934.99.9001


References

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2: Schattauer SS, Land BB, Reichard KL, Abraham AD, Burgeno LM, Kuhar JR, Phillips PEM, Ong SE, Chavkin C. Peroxiredoxin 6 mediates Gαi protein-coupled receptor inactivation by cJun kinase. Nat Commun. 2017 Sep 29;8(1):743. doi: 10.1038/s41467-017-00791-2. PubMed PMID: 28963507; PubMed Central PMCID: PMC5622097.

3: Zádor F, Balogh M, Váradi A, Zádori ZS, Király K, Szűcs E, Varga B, Lázár B, Hosztafi S, Riba P, Benyhe S, Fürst S, Al-Khrasani M. 14-O-Methylmorphine: A Novel Selective Mu-Opioid Receptor Agonist with High Efficacy and Affinity. Eur J Pharmacol. 2017 Nov 5;814:264-273. doi: 10.1016/j.ejphar.2017.08.034. Epub 2017 Aug 30. PubMed PMID: 28864212.

4: Przybysz KR, Werner DF, Diaz MR. Age-dependent regulation of GABA transmission by kappa opioid receptors in the basolateral amygdala of Sprague-Dawley rats. Neuropharmacology. 2017 May 1;117:124-133. doi: 10.1016/j.neuropharm.2017.01.036. Epub 2017 Feb 3. PubMed PMID: 28163104; PubMed Central PMCID: PMC5386797.

5: Karkhanis AN, Huggins KN, Rose JH, Jones SR. Switch from excitatory to inhibitory actions of ethanol on dopamine levels after chronic exposure: Role of kappa opioid receptors. Neuropharmacology. 2016 Nov;110(Pt A):190-197. doi: 10.1016/j.neuropharm.2016.07.022. Epub 2016 Jul 20. PubMed PMID: 27450094; PubMed Central PMCID: PMC5028299.

6: Treskatsch S, Shaqura M, Dehe L, Feldheiser A, Roepke TK, Shakibaei M, Spies CD, Schäfer M, Mousa SA. Upregulation of the kappa opioidergic system in left ventricular rat myocardium in response to volume overload: Adaptive changes of the cardiac kappa opioid system in heart failure. Pharmacol Res. 2015 Dec;102:33-41. doi: 10.1016/j.phrs.2015.09.005. Epub 2015 Sep 10. PubMed PMID: 26365878.

7: Zhou L, Stahl EL, Lovell KM, Frankowski KJ, Prisinzano TE, Aubé J, Bohn LM. Characterization of kappa opioid receptor mediated, dynorphin-stimulated [35S]GTPγS binding in mouse striatum for the evaluation of selective KOR ligands in an endogenous setting. Neuropharmacology. 2015 Dec;99:131-41. doi: 10.1016/j.neuropharm.2015.07.001. Epub 2015 Jul 6. PubMed PMID: 26160155; PubMed Central PMCID: PMC4655192.

8: Wang PC, Ho IK, Lee CW. Buprenorphine-elicited alteration of adenylate cyclase activity in human embryonic kidney 293 cells coexpressing κ-, μ-opioid and nociceptin receptors. J Cell Mol Med. 2015 Nov;19(11):2587-96. doi: 10.1111/jcmm.12644. Epub 2015 Jul 8. PubMed PMID: 26153065; PubMed Central PMCID: PMC4627564.

9: Bauer CT, Banks ML, Blough BE, Negus SS. Role of 5-HT₂C receptors in effects of monoamine releasers on intracranial self-stimulation in rats. Psychopharmacology (Berl). 2015 Sep;232(17):3249-58. doi: 10.1007/s00213-015-3982-2. Epub 2015 Jun 5. PubMed PMID: 26041338; PubMed Central PMCID: PMC4536134.

10: Tejeda HA, Hanks AN, Scott L, Mejias-Aponte C, Hughes ZA, O'Donnell P. Prefrontal Cortical Kappa Opioid Receptors Attenuate Responses to Amygdala Inputs. Neuropsychopharmacology. 2015 Dec;40(13):2856-64. doi: 10.1038/npp.2015.138. Epub 2015 May 14. PubMed PMID: 25971593; PubMed Central PMCID: PMC4864622.

11: Lovell KM, Frankowski KJ, Stahl EL, Slauson SR, Yoo E, Prisinzano TE, Aubé J, Bohn LM. Structure-activity relationship studies of functionally selective kappa opioid receptor agonists that modulate ERK 1/2 phosphorylation while preserving G protein over βarrestin2 signaling bias. ACS Chem Neurosci. 2015 Aug 19;6(8):1411-9. doi: 10.1021/acschemneuro.5b00092. Epub 2015 May 1. Erratum in: ACS Chem Neurosci. 2017 Jul 19;8(7):1628. PubMed PMID: 25891774; PubMed Central PMCID: PMC4830356.

12: Negus SS, Neddenriep B, Altarifi AA, Carroll FI, Leitl MD, Miller LL. Effects of ketoprofen, morphine, and kappa opioids on pain-related depression of nesting in mice. Pain. 2015 Jun;156(6):1153-60. doi: 10.1097/j.pain.0000000000000171. PubMed PMID: 25827812; PubMed Central PMCID: PMC4766843.

13: Guerrieri E, Mallareddy JR, Tóth G, Schmidhammer H, Spetea M. Synthesis and pharmacological evaluation of [(3)H]HS665, a novel, highly selective radioligand for the kappa opioid receptor. ACS Chem Neurosci. 2015 Mar 18;6(3):456-63. doi: 10.1021/cn5002792. Epub 2014 Dec 24. PubMed PMID: 25496417.

14: Arida RM, Gomes da Silva S, de Almeida AA, Cavalheiro EA, Zavala-Tecuapetla C, Brand S, Rocha L. Differential effects of exercise on brain opioid receptor binding and activation in rats. J Neurochem. 2015 Jan;132(2):206-17. doi: 10.1111/jnc.12976. Epub 2014 Nov 17. PubMed PMID: 25330347.

15: Wang ZL, Fang Q, Han ZL, Pan JX, Li XH, Li N, Tang HH, Wang P, Zheng T, Chang XM, Wang R. Opposite effects of neuropeptide FF on central antinociception induced by endomorphin-1 and endomorphin-2 in mice. PLoS One. 2014 Aug 4;9(8):e103773. doi: 10.1371/journal.pone.0103773. eCollection 2014. PubMed PMID: 25090615; PubMed Central PMCID: PMC4121275.

16: Kuo A, Wyse BD, Meutermans W, Smith MT. In vivo profiling of seven common opioids for antinociception, constipation and respiratory depression: no two opioids have the same profile. Br J Pharmacol. 2015 Jan;172(2):532-48. doi: 10.1111/bph.12696. Epub 2014 Jul 1. PubMed PMID: 24641546; PubMed Central PMCID: PMC4292966.

17: Dimattio KM, Yakovleva TV, Aldrich JV, Cowan A, Liu-Chen LY. Zyklophin, a short-acting kappa opioid antagonist, induces scratching in mice. Neurosci Lett. 2014 Mar 20;563:155-9. doi: 10.1016/j.neulet.2014.01.022. Epub 2014 Feb 3. PubMed PMID: 24503508; PubMed Central PMCID: PMC4154496.

18: Gear RW, Bogen O, Ferrari LF, Green PG, Levine JD. NOP receptor mediates anti-analgesia induced by agonist-antagonist opioids. Neuroscience. 2014 Jan 17;257:139-48. doi: 10.1016/j.neuroscience.2013.10.061. Epub 2013 Nov 1. PubMed PMID: 24188792; PubMed Central PMCID: PMC3947912.

19: Gilpin NW, Roberto M, Koob GF, Schweitzer P. Kappa opioid receptor activation decreases inhibitory transmission and antagonizes alcohol effects in rat central amygdala. Neuropharmacology. 2014 Feb;77:294-302. doi: 10.1016/j.neuropharm.2013.10.005. Epub 2013 Oct 21. PubMed PMID: 24157490; PubMed Central PMCID: PMC3873141.

20: Vardy E, Mosier PD, Frankowski KJ, Wu H, Katritch V, Westkaemper RB, Aubé J, Stevens RC, Roth BL. Chemotype-selective modes of action of κ-opioid receptor agonists. J Biol Chem. 2013 Nov 29;288(48):34470-83. doi: 10.1074/jbc.M113.515668. Epub 2013 Oct 11. PubMed PMID: 24121503; PubMed Central PMCID: PMC3843062.