U-69593
- CAS No.
- 96744-75-1
- Chemical Name:
- U-69593
- Synonyms
- U-69593;U-69593 SELECTIVE K OPIOID AG;U-69593, kappa1-opioid receptor agonist;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
- CBNumber:
- CB0432261
- Molecular Formula:
- C22H32N2O2
- Molecular Weight:
- 356.5
- MDL Number:
- MFCD05664586
- MOL File:
- 96744-75-1.mol
- MSDS File:
- SDS
| 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 |
| EWG's Food Scores | 1 |
| FDA UNII | J5S4K6TKTG |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
U-69593 Chemical Properties,Uses,Production
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.