96744-75-1 Usage
Description
U-69593, also known as a monocarboxylic acid amide, is a selective κ-opioid receptor agonist derived from the formal condensation between the carboxy group of phenylacetic acid and the secondary amino group of (5R,7S,8S)-N-methyl-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-amine. It is an oxaspiro compound, a N-alkylpyrrolidine, an organic heterobicyclic compound, and a monocarboxylic acid amide. U-69593 has a role as an anti-inflammatory agent, a diuretic, and a safe opioid analgesic.
Uses
Used in Pharmaceutical Industry:
U-69593 is used as a selective κ-opioid receptor agonist for its analgesic properties, providing pain relief without the risk of addiction associated with traditional opioids.
Used in Anti-inflammatory Applications:
U-69593 is used as an anti-inflammatory agent, helping to reduce inflammation and alleviate pain in various conditions.
Used in Diuretic Therapy:
U-69593 is used as a diuretic, promoting the increase of urine output and helping to manage fluid retention and blood pressure in patients with edema or hypertension.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 96744-75-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,6,7,4 and 4 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 96744-75:
(7*9)+(6*6)+(5*7)+(4*4)+(3*4)+(2*7)+(1*5)=181
181 % 10 = 1
So 96744-75-1 is a valid CAS Registry Number.
InChI:InChI=1/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-/m1/s1
96744-75-1Relevant articles and documents
A practical synthesis of the kappa opioid receptor selective agonist (+)-5R,7S,8S-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxospiro[4,5]dec-8-yl] benzeneacetamide (U69,593)
McElroy, Timothy,Thomas, James B.,Brine, George A.,Navarro, Hernan A.,Deschamps, Jeffrey,Carroll, F. Ivy
, p. 943 - 947 (2008/12/23)
A novel approach to the synthesis of the kappa opioid receptor agonist U69,593 has been developed. This approach improves upon current literature methods by substituting stable and isolable cyclic sulfates for the unstable epoxides. The new approach provides access to gram quantities of the target compound and displays excellent control of the relative stereochemistry. The absolute stereochemistry as well as biological activity of the U69,593 produced by this new method was verified using X-ray crystal structure analysis and binding assays for the kappa opioid receptor. Georg Thieme Verlag Stuttgart.
