182417-73-8

Basic information

• Product Name: (+)-3-[1(R)-[4-Allyl-2(S),5(R)-dimethylpiperazin-1-yl]-1-(3-hydroxyphenyl)methyl]-N-(3-fluorophenyl)-N-methylbenzamide
• Synonyms: Org-41793; 3290W93; DPI-3290W93; DPI-3290
• CAS NO: 182417-73-8
• Molecular Formula: C₃₀H₃₄FN₃O₂
• Molecular Weight: 487.62278
• Mol File: 182417-73-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-3-[1(R)-[4-Allyl-2(S),5(R)-dimethylpiperazin-1-yl]-1-(3-hydroxyphenyl)methyl]-N-(3-fluorophenyl)-N-methylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-3-[1(R)-[4-Allyl-2(S),5(R)-dimethylpiperazin-1-yl]-1-(3-hydroxyphenyl)methyl]-N-(3-fluorophenyl)-N-methylbenzamide(182417-73-8)
• EPA Substance Registry System: (+)-3-[1(R)-[4-Allyl-2(S),5(R)-dimethylpiperazin-1-yl]-1-(3-hydroxyphenyl)methyl]-N-(3-fluorophenyl)-N-methylbenzamide(182417-73-8)

Safety Data

• Hazardous Substances Data: 182417-73-8(Hazardous Substances Data)

Upstream product

• 155836-83-2 (+)-3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)benzonitrile 
• 155836-82-1 (+)-3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-bromobenzyl)phenol 
• 155767-23-0 α-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)-benzyl alcohol 
• 155767-24-1 α-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)benzyl chloride 
• 1428-10-0 N-(3-fluorophenyl)formamide 
• 1978-37-6 3-fluoro-N-methylaniline 
• 65423-56-5 1-bromo-3-[(tert-butyldimethylsilyl)oxy]benzene 
• 591-20-8 3-Bromophenol 
• 168155-49-5 tert-butyldimethylsilyl 3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)benzoate 
• 168155-50-8 3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)benzoyl chloride 
• 500912-24-3 (2R,5S)-1-Allyl-4-{(3-bromo-phenyl)-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-methyl}-2,5-dimethyl-piperazine 
• 168749-06-2 (+)-3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)benzoic acid 

Downstream Products

• 168155-43-9 3-((R)-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-(N-(3-fluorophenyl)-N-methylcarbamoyl)benzyl)phenyl monophosphate 

Relevant articles and documents

3-(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl) -3-hydroxybenzyl)-N-alkyl-N-arylbenzamides: Potent, non-peptidic agonists of both the μ and δ opioid receptors

Opioid analgesics with both μ and δ opioid receptor activation represent a new approach to the treatment of severe pain with an improved safety profile. Compounds with this profile may exhibit strong analgesic properties due to μ agonism, with a reduced side effect profile resulting from δ agonism. Replacing the p-diethylamide of the known potent δ opioid receptor selective agonist BW373U86 with a m-diethylamide resulted in a compound with agonist activity at both the μ and δ opioid receptors. Modifying the amide to an N-methyl-N-phenylamide increased agonist potency at both receptors. A series of 3-(αR)-α((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl) -3-hydroxybenzyl)-N-alkyl-N-arylbenzamides have been made to explore the structure-activity relationship (SAR) around the N-methyl-N-phenylamide. Several potent agonists of both the μ and δ opioid receptors have been identified, including (+)-3-((αR)-α ((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3- hydroxybenzyl)-N-(4-flourophenyl)-N-methylbenzamide (23), which has EC50 values of 0.67 and 1.1 nM at the μ (guinea pig ileum assay) and δ (mouse vas deferens assay) opioid receptors, respectively.

OPIOID COMPOUNDS AND METHODS FOR USING SAME

Diarylmethyl piperazine compounds having utility as exogenous receptor combinant species for binding with receptors such as delta, mu, sigma, and/or kappa receptors are disclosed. Compounds of the invention may be employed as conjugates in agonist/antagonist pairs for transductional monitoring and assays of neurotransmitter function, and also variously exhibit therapeutic utility, including mediating analgesia, and possessing utility for the treatment of diarrhea, urinary incontinence, mental illness, drug and alcohol addiction/overdose, lung edema, depression, asthma, emphysema, cough, and apnea, respiratory depression, cognitive disorders, emesis and gastrointestinal disorders.