U103

Sigma-Aldrich

U-69593

solid

Synonym(s):
U69593, (+)-(5α,7α,8β)-N-Methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-benzeneacetamide
Empirical Formula (Hill Notation):
C22H32N2O2
CAS Number:
Molecular Weight:
356.50
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

form

solid

optical activity

[α]/D +7.8°, c = 0.825 in methanol(lit.)

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 10 mg/mL
0.1 M HCl: >40 mg/mL
ethanol: >40 mg/mL
0.1 M NaOH: insoluble
H2O: insoluble

storage temp.

2-8°C

SMILES string

CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)Cc4ccccc4

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

InChI key

PGZRDDYTKFZSFR-ONTIZHBOSA-N

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Packaging

5 mg in glass bottle
25 mg in poly bottle

Biochem/physiol Actions

U-69593 is a selective κ opioid receptor agonist. U-69593 is known to inhibit cocaine sensitization in meso-limbic dopamine neurons by normalizing basal overflow of dopamine.

Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Preparation Note

U-69593 is soluble in 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin (10 mg/ml), 0.1 M HCl (>40 mg/ml), and ethanol (>40 mg/ml). However, it is insoluble in 0.1 M NaOH and water.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Gregory P McLennan et al.
Journal of neurochemistry, 107(6), 1753-1765 (2008-11-19)
GTP binding regulatory protein (G protein)-coupled receptors can activate MAPK pathways via G protein-dependent and -independent mechanisms. However, the physiological outcomes correlated with the cellular signaling events are not as well characterized. In this study, we examine the involvement of...
S Stevens Negus et al.
Experimental and clinical psychopharmacology, 16(5), 386-399 (2008-10-08)
Micro opioid receptor agonists are clinically valuable as analgesics; however, their use is limited by high abuse liability. Kappa opioid agonists also produce antinociception, but they do not produce micro agonist-like abuse-related effects, suggesting that they may enhance the antinociceptive...
S Stevens Negus et al.
Psychopharmacology, 210(2), 149-159 (2010-01-27)
Selective, centrally acting kappa opioid agonists produce antinociception in a wide range of preclinical assays, but these compounds perform poorly as analgesics in humans. This discrepancy may be related to the behavioral depressant effects of kappa agonists. Kappa antagonists do...
Hugo A Tejeda et al.
Psychopharmacology, 210(2), 231-240 (2010-03-17)
Kappa-opioid receptor (KOR) agonists produce dysphoria and psychotomimesis in humans. KORs are enriched in the prefrontal cortex and other brain regions that regulate mood and cognitive function. Dysregulation of the dynorphin/KOR system has been implicated in the pathogenesis of schizophrenia...
T Nakagawa et al.
Japanese journal of pharmacology, 81(4), 353-361 (2000-02-11)
Chronic and/or sustained opioid treatment has been shown to result in development of sensitization of the adenylyl cyclase (AC) system or cAMP overshoot. In this study, we investigated the molecular mechanism responsible for sensitization of the AC system using CHO...

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