U103

U-69593

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
• MDL number: MFCD05664586
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278769
• NACRES: NA.77

Properties

• 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)

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.

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 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