109620-49-7

Basic information

• Product Name: (+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE
• Synonyms: TRANS-(1R,2R)-3,4-DICHLORO-N-METHYL-N-[2-(1-PYRROLIDINYL)CYCLOHEXYL]-BENZENEACETAMIDE HYDROCHLORIDE;(+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE;TRANS-(+)-3,4-DICHLORO-N-METHYL-N-[2-(1-PYRROLIDINYL)-CYCLOHEXYL]BENZENEACETAMIDE HYDROCHLORIDE;(+)-U-50488 HYDROCHLORIDE
• CAS NO: 109620-49-7
• Molecular Formula: C₁₉H₂₆Cl₂N₂O*ClH
• Molecular Weight: 405.79
• Mol File: 109620-49-7.mol
• Article Data: 1

Chemical Properties

• Appearance: white/solid
• Storage Temp.: 2-8°C
• Solubility: H2O: 11 mg/mL
• CAS DataBase Reference: (+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE(109620-49-7)
• EPA Substance Registry System: (+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE(109620-49-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 109620-49-7(Hazardous Substances Data)

Usage

Uses

(+)-U-50488 Hydrochloride is a k-opioid agonist with no μ-opioid receptor effects in vitro, which may be used in the treatment of African trypanosomiasis.

Upstream product

• 67198-34-9 trans-(+/-)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine 
• 67198-13-4 trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidynyl)-cyclohexyl]benzeneacetamide 
• 130993-58-7 Methanesulfonic acid (1R,2R)-2-pyrrolidin-1-yl-cyclohexyl ester 
• 286-20-4 cyclohexane-1,2-epoxide 
• 69420-67-3 (+/-)-trans-[2-(pyrrolidinyl)]cyclohexanol 

Relevant articles and documents

Optimisation of the Anti-Trypanosoma brucei Activity of the Opioid Agonist U50488

Screening of the Sigma-Aldrich Library of Pharmacologically Active Compounds (LOPAC) against cultured Trypanosoma brucei, the causative agent of African sleeping sickness, resulted in the identification of a number of compounds with selective antiproliferative activity over mammalian cells. These included (+)-(1R,2R)-U50488, a weak opioid agonist with an EC50 value of 59nM as determined in our T.brucei invitro assay reported previously. This paper describes the modification of key structural elements of U50488 to investigate structure-activity relationships (SAR) and to optimise the antiproliferative activity and pharmacokinetic properties of this compound.