Skip to Content
Merck
All Photos(2)

Documents

U103

Sigma-Aldrich

U-69593

solid

Synonym(s):

(+)-(5α,7α,8β)-N-Methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-benzeneacetamide, U69593

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C22H32N2O2
CAS Number:
96744-75-1
Molecular Weight:
356.50
MDL number:
MFCD05664586
UNSPSC Code:
12352200
PubChem Substance ID:
24278769
NACRES:
NA.77

form

solid

Quality Level

100

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

Gene Information

human ... OPRD1(4985) , OPRK1(4986) , OPRM1(4988)
mouse ... Oprk1(18387)
rat ... Oprd1(24613) , Oprk1(29335) , Oprm1(25601)

Looking for similar products? Visit Product Comparison Guide

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ajay S Yekkirala et al.
ACS chemical neuroscience, 1(2), 146-154 (2010-02-17)
Research in the opioid field has relied heavily on the use of standard agonist ligands such as morphine, [d-Ala(2)-MePhe(4)-Glyol(5)]enkephalin (DAMGO), U69593, bremazocine, [d-Pen(2)d-Pen(5)]enkephalin (DPDPE), and deltorphin-II as tools for investigating the three major types of opioid receptors, MOP (μ), KOP
S Schenk et al.
Psychopharmacology, 151(1), 85-90 (2000-08-25)
Results of a previous study indicated that prior administration of the kappa-opioid receptor agonist, U69593, blocked the ability of cocaine to reinstate extinguished cocaine-taking behavior. In order to determine whether the effect of U69593 was specific to cocaine or was
Lisa E Baker et al.
Psychopharmacology, 203(2), 203-211 (2009-01-21)
Research interests regarding the psychopharmacology of salvinorin A have been motivated by the recreational use and widespread media focus on the hallucinogenic plant, Salvia divinorum. Additionally, kappa opioid (KOP) receptor ligands may have therapeutic potential in the treatment of some
Xu Zhang et al.
Behavioural brain research, 236(1), 8-15 (2012-09-04)
Within a biopsychosocial model of pain, pain is seen as a conscious experience modulated by mental, emotional and sensory mechanisms. Recently, using a rodent visceral pain assay that combines the colorectal distension (CRD) model with the conditioned place avoidance (CPA)
Reagan L Pennock et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(1), 281-288 (2011-01-07)
Hypothalamic proopiomelanocortin (POMC) neurons release the endogenous opioid beta-endorphin and POMC neuron activity is inhibited by opioids, leading to the proposal that beta-endorphin acts to provide feedback inhibition. However, both intrinsic properties and synaptic inputs contribute to the regulation of
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service