ChemicalBook > CAS DataBase List > U-69593

U-69593

Product Name
U-69593
CAS No.
96744-75-1
Chemical Name
U-69593
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)-(-)-
CBNumber
CB0432261
Molecular Formula
C22H32N2O2
Formula Weight
356.5
MOL File
96744-75-1.mol
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U-69593 Property

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.)
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
U103
Product name
U-69593
Purity
solid
Packaging
5mg
Price
$232
Updated
2024/03/01
Sigma-Aldrich
Product number
U103
Product name
U-69593
Purity
solid
Packaging
25mg
Price
$826
Updated
2024/03/01
Alfa Aesar
Product number
J67220
Product name
U-69593
Purity
99%
Packaging
5mg
Price
$205
Updated
2023/06/20
Alfa Aesar
Product number
J67220
Product name
U-69593
Purity
99%
Packaging
25mg
Price
$726
Updated
2023/06/20
Cayman Chemical
Product number
13255
Product name
U-69593
Purity
≥95%
Packaging
1mg
Price
$68
Updated
2024/03/01
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U-69593 Chemical Properties,Usage,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.

U-69593 Preparation Products And Raw materials

Raw materials

Preparation Products

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U-69593 Suppliers

China 31 Germany 1 Switzerland 2 United Kingdom 1 United States 9 Global 44
3B Pharmachem (Wuhan) International Co.,Ltd.
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View Lastest Price from U-69593 manufacturers

Dorne Chemical Technology co. LTD
Product
U-69593 96744-75-1
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
100kg
Release date
2024-03-26
Shandong Hanjiang Chemical Co., Ltd
Product
U-69593 96744-75-1
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10T
Release date
2024-01-25
Career Henan Chemical Co
Product
U-69593 96744-75-1
Price
US $1.00/KG
Min. Order
1G
Purity
98%
Supply Ability
100KG
Release date
2018-08-15

96744-75-1, U-69593Related Search:

[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

  • U-69593
  • (+)-(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
  • U-69593 SELECTIVE K OPIOID AG
  • (5A,7A,8B)-(-)-N-METHYL-(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)-
  • Benzeneacetamide, N-methyl-N-(7-(1-pyrrolidinyl)-1-oxaspiro(4.5)dec-8-yl)-, (5alpha,7alpha,8beta)-(-)-
  • 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
  • U69593, (+)-(5α,7α,8β)-N-Methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-benzeneacetamide
  • 96744-75-1
  • 6744-75-1