U-69593 Struktur

U-69593

Bezeichnung:U-69593

CAS-Nr96744-75-1

Englisch Name:U-69593

CBNumberCB0432261

SummenformelC22H32N2O2

Molgewicht356.5

MOL-Datei96744-75-1.mol

U-69593 physikalisch-chemischer Eigenschaften

Schmelzpunkt	120-123℃
Siedepunkt	518.7±50.0 °C(Predicted)
Dichte	1.13
RTECS-Nr.	CY1490060
storage temp.	2-8°C
Löslichkeit	H₂O: 14 mg/mL
Aggregatzustand	solid
pka	9.15±0.20(Predicted)
Farbe	white
Optische Aktivität	[α]/D +7.8°, c = 0.825 in methanol(lit.)

Sicherheit

WGK Germany

U-69593 Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden
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.
Biologische Funktion
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 Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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