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Merck
CN

U103

Sigma-Aldrich

U-69593

selective κ opioid receptor agonist, solid

Synonym(s):

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

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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

Key Documents

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Product Name

U-69593, solid

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)

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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

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Certificates of Analysis (COA)

Lot/Batch Number
0000382428
0000382428
0000102364
0000073185
0000030456

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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
C A Heidbreder et al.
Neuroreport, 5(14), 1797-1800 (1994-09-08)
Repeated intermittent administration of cocaine (20 mg kg-1, i.p.) for 3 days dramatically increased basal dopamine (DA) overflow in the nucleus accumbens (ACB) 48 h after the final daily injection. This cocaine pretreatment also produced a significant increase in stereotypy
Carmel M McDermott et al.
The Journal of physiology, 589(Pt 14), 3517-3532 (2011-05-25)
The dentate gyrus of the hippocampus is thought to control information flow into the rest of the hippocampus. Under pathological conditions, such as epilepsy, this protective feature is circumvented and uninhibited activity flows throughout the hippocampus. Many factors can modulate
Karl J Iremonger et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 29(22), 7349-7358 (2009-06-06)
Opioid signaling in the CNS is critical for controlling cellular excitability, yet the conditions under which endogenous opioid peptides are released and the precise mechanisms by which they affect synaptic transmission remain poorly understood. The opioid peptide dynorphin is present
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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