U103

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
• 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

Properties

• Product Name: U-69593, solid
• form: solid
• Quality Segment: 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)

Description

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[1].

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)