N-methyl-2-phenyl-N-[(5R,7S,8S)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-yl]acetamide

• ChemBase ID: 130069
• Molecular Formular: C22H32N2O2
• Molecular Mass: 356.50168
• Monoisotopic Mass: 356.24637827
• SMILES: O=C(N([C@H]1CC[C@]2(OCCC2)C[C@@H]1N1CCCC1)C)Cc1ccccc1
• Canonical SMILES: O=C(N([C@H]1CC[C@]2(C[C@@H]1N1CCCC1)CCCO2)C)Cc1ccccc1
• InChI: 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
• InChIKey: PGZRDDYTKFZSFR-ONTIZHBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-methyl-2-phenyl-N-[(5R,7S,8S)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-yl]acetamide
• IUPAC Traditional name: N-methyl-2-phenyl-N-[(5R,7S,8S)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-yl]acetamide
• Synonyms: U-69,593; (+)-(5α,7α,8β)-N-Methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-benzeneacetamide; U69593; U-69593

Database IDs

• CAS Number: 96744-75-1
• MDL Number: MFCD05664586
• PubChem SID: 24278769; 162224354
• PubChem CID: 105104
• CHEMBL: 440765
• Chemspider ID: 94828
• IUPHAR ligand ID: 1655
• Wikipedia Title: U-69,593

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.82914925
• LogD (pH = 7.4): 0.2654632
• Log P: 2.6034946
• Molar Refractivity: 104.4324 cm^3
• Polarizability: 41.03713 Å^3
• Polar Surface Area: 32.78 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: >40 mg/mL; 0.1 M NaOH: insoluble; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble10 mg/mL; ethanol: >40 mg/mL; H2O: insoluble
• Apperance: white solid
• Optical Rotation: [α]/D +7.8°, c = 0.825 in methanol(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... OPRD1(4985), OPRK1(4986), OPRM1(4988)mouse ... Oprk1(18387)rat ... Oprd1(24613), Oprk1(29335), Oprm1(25601)

DETAILS

Sigma Aldrich - U103

Biochem/physiol Actions
U-69593 is a selective κ opioid receptor agonist.