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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

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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

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

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’.

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