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U103

U-69593

Name: U-69593
Brand: SIGMA

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

UNSPSC Code:

12352200

PubChem Substance ID:

24278769

NACRES:

NA.77

MDL number:

MFCD05664586

Form:

solid

Quality level:

100

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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)

Related Categories

Bioactive Small Molecules

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats.

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

Vagus nerve stimulation modulates visceral pain-related affective memory.

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)

Agonist-selective recruitment of engineered protein probes and of GRK2 by opioid receptors in living cells.

Miriam Stoeber et al.

eLife, 9 (2020-02-26)

G protein-coupled receptors (GPCRs) signal through allostery, and it is increasingly clear that chemically distinct agonists can produce different receptor-based effects. It has been proposed that agonists selectively promote receptors to recruit one cellular interacting partner over another, introducing allosteric

Differential expression and sensitivity of presynaptic and postsynaptic opioid receptors regulating hypothalamic proopiomelanocortin neurons.

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

U-69593 prevents cocaine sensitization by normalizing basal accumbens dopamine.

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

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Global Trade Item Number

SKU	GTIN
U103-25MG	04061832561349
U103-5MG	04061832561356

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