112465-94-8

Basic information

• Product Name: U-54494A HYDROCHLORIDE
• Synonyms: CIS (+/-)-3,4-DICHLORO-N-METHYL-N-[2-(1-PYRROLIDINYL)CYCLOHEXYL]BENZAMIDE HCL;CIS-(+/-)-3,4-DICHLORO-N-METHYL-N-[2-(1-PYRROLIDINYL)CYCLOHEXYL]BENZAMIDE HYDROCHLORIDE;U-54494A;U-54494A HYDROCHLORIDE;U-54494AHCl
• CAS NO: 112465-94-8
• Molecular Formula: C₁₈H₂₄Cl₂N₂O*ClH
• Molecular Weight: 405.79
• Mol File: 112465-94-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 496.5 °C at 760 mmHg
• Flash Point: 254.1 °C
• Appearance: White to off-white solid.
• Vapor Pressure: 5.38E-10mmHg at 25°C
• Storage Temp.: Store at RT
• CAS DataBase Reference: U-54494A HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: U-54494A HYDROCHLORIDE(112465-94-8)
• EPA Substance Registry System: U-54494A HYDROCHLORIDE(112465-94-8)

Safety Data

• Hazardous Substances Data: 112465-94-8(Hazardous Substances Data)

Usage

Biological Activity

κ -opioid agonist and anticonvulsant. Perhaps acts as an NMDA antagonist.

InChI:InChI=1/C18H24Cl2N2O.ClH/c1-21(18(23)13-8-9-14(19)15(20)12-13)16-6-2-3-7-17(16)22-10-4-5-11-22;/h8-9,12,16-17H,2-7,10-11H2,1H3;1H/t16-,17+;/m1./s1

Upstream product

• 67198-34-9 (+/-)-cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine 
• 3024-72-4 3,4-dichlorobenzoyl chloride 

Relevant articles and documents

Synthesis and evaluation of N-substituted cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamines as high affinity σ receptor ligands. Identification of a new class of highly potent and selective σ receptor probes

Certain benzeneacetamides [(-)- and (+)-cis-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzenea cetamide] were recently reported to be potent σ receptor ligands. In order to determine whether efficacy for the σ receptor could be improved, a series of compounds related to the benzeneacetamides, N-substituted cis-2-(1-pyrrolidinyl)-N-methylcyclohexylamines, were synthesized and their structure-activity requirements were determined. The compounds were synthesized by starting with the previously reported (±)-, 1S,2R-(+)-, and 1R,2S-(-)-cis-2-(1-pyrrolidinyl)-N-methylcyclohexylamines. Analysis of σ ([3H](+)-3-PPP), κ ([3H]bremazocine and [3H]U69,593), dopamine-d2 ([3H](-)-sulpiride), and phencyclidine (PCP) ([3H]TCP) receptor binding in guinea pig brain revealed a number of highly potent and selective σ receptor ligands. Notably, 1S,2R-cis-(-)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-(2-naphthyl)ac etamide [(-)-29] (K(i) = 8.66 ± 0.35 nM), (±)-cis-2-amino-4,5-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl ]benzeneacetamide [(±)-17] (K(i) = 11 ± 3 nM), 1S,2R-(-)-cis-N-methyl-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidin yl)cyclohexylamine [(-)-44] (K(i) = 1.3 ± 0.3 nM), and 1R,2S-(+)-cis-N-methyl-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidin yl)cyclohexylamine. [(+)-44] (K(i) = 6 ± 3 nM) exhibited very high affinity at σ receptors, by displacement of [3H]-(+)-3-(3-hydroxyphenyl)-N-(1-propyl)piperidine ([3H]-(+)-3-PPP). These compounds showed significant affinity for κ, dopamine, or PCP receptors, making them valuable tools for the study of σ receptors. Furthermore, these compounds also exhibited enantioselectivity ranging from 5-fold for (+)- and (-)-44 to 160-fold for (+)- and (-)-29. Several other compounds showed equivalent selectivity but displayed lower σ receptor affinity.