U-69593 Chemical Properties

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.)

Safety Information

WGK Germany 

3

U-69593 Usage And Synthesis

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.

U-69593(96744-75-1)Related Product Information

• [3H]U-69593
• (1S,2S)-N,N,N''N''-TETRAMETHYL-1,2-CYCLOHEXANEDIAMINE
• Enadoline
• U-69,593, [PHENYL-3,4-3H]-
• (1S,2S)-N,N'-Dimethyl-1,2-cyclohexanediamine
• CHEMBRDG-BB 4018237
• U-69593
• trans-4-(Dimethylamino)cyclohexanol
• (1S,2S)-(+)-N,N-Dimethylcyclohexane-1,2-diamine
• U-62066 (SPIRADOLINE MESYLATE) K-OPIOID AGONIST