| Identification | Back Directory | [Name]
U-69593 | [CAS]
96744-75-1 | [Synonyms]
U-69593
U-69593 SELECTIVE K OPIOID AG
N-Methyl-N-(7-(1-pyrrolidinyl)-1-oxaspiro(4,5)dec-8-yl)benzeneacetamide
N-Methyl-N-[(5R,7S,8S)-7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]benzeneacetamide
Benzeneacetamide, N-methyl-N-((5R,7S,8S)-7-(1-pyrrolidinyl)-1-oxaspiro(4.5)dec-8-yl)-
(5A,7A,8B)-(-)-N-METHYL-(7-(1-PYRROLIDINYL)-1-OXASPIRO (4.5)DEC-8- YL)BENZENEACETAMIDE)
U69593, (+)-(5α,7α,8β)-N-Methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-benzeneacetamide
(+)-(5ALPHA,7ALPHA,8BETA)-N-METHYL-N-[7-(1-PYRROLIDINYL)-1-OXASPIRO[4.5]DEC-8-YL]-BENZENEACETAMIDE
(5ALPHA,7ALPHA,8BETA)-(+)-N-METHYL-N-(7-[1-PYRROLIDINYL]-1-OXASPIRO[4.5]DEC-8-YL)-BENZENEACETAMIDE
Benzeneacetamide, N-methyl-N-(7-(1-pyrrolidinyl)-1-oxaspiro(4.5)dec-8-yl)-, (5alpha,7alpha,8beta)-(-)- | [Molecular Formula]
C22H32N2O2 | [MDL Number]
MFCD05664586 | [MOL File]
96744-75-1.mol | [Molecular Weight]
356.5 |
| Chemical Properties | Back Directory | [Melting point ]
120-123℃ | [Boiling point ]
518.7±50.0 °C(Predicted) | [density ]
1.13 | [RTECS ]
CY1490060 | [storage temp. ]
2-8°C | [solubility ]
H2O: 14 mg/mL | [form ]
solid | [pka]
9.15±0.20(Predicted) | [color ]
white | [optical activity]
[α]/D +7.8°, c = 0.825 in methanol(lit.) | [Water Solubility ]
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 10mg/mL
0.1 M HCl: >40mg/mL
ethanol: >40mg/mL
0.1 M NaOH: insoluble
H2O: insoluble |
| Hazard Information | Back Directory | [Uses]
U-69593 is a selective κ-opioid receptor agonist. A safe opioid analgesic. | [Definition]
ChEBI: U69593 is a monocarboxylic acid amide obtained by formal condensation between the carboxy group of phenylacetic acid and the secodary amino group of (5R,7S,8S)-N-methyl-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-amine. It has a role as a kappa-opioid receptor agonist, an anti-inflammatory agent and a diuretic. It is an oxaspiro compound, a N-alkylpyrrolidine, an organic heterobicyclic compound and a monocarboxylic acid amide. | [Biological Functions]
U-69593 is a single enantiomer with very high selectivity for the kappa receptor in vitro (mu/kappa ratio = 484). It was radiolabelled by a catalytic exchange of tritium for the two aromatic chlorine substituents of the precursor. This ligand is commercially available and has been widely used as a radiolabel for the kappa receptor.
in spinal cordslice preparations from the 9-16-day-old rat,U-69593 produced a na-loxone-reversible depression of spontaneous and electrically evoked activityin dorsal horn neurones. | [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. | [Structure and conformation]
An X-ray analysis of the crystal structures of U-50488 and U-69593 have been determined. The cyclohexane ring adopts a chair conformation with both nitrogen substituents attached equatorially The amide bond is in a trans conformation and the absolute stereochemistry of the kappa opioid active enantiomer of U-50488 is [S,S]. There appears to be some confusion concerning the ab-solute stereochemistry of U-69593.The structure in the publication describ-ing the X-ray crystallography is drawn as 5R,7S,8S,but the title of thispaper,which gives the full chemical name of U-69593, indicates 5S,7S,8S. |
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