127648-30-0

Basic information

• Product Name: 2-carbomethoxy-3-(4-fluorophenyl)nortropane
• Synonyms: 2-carbomethoxy-3-(4-fluorophenyl)nortropane;(1R,2S,3S,5S)-Methyl 3-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS NO: 127648-30-0
• Molecular Formula: C₁₅H₁₈FNO₂
• Molecular Weight: 263.31
• Mol File: 127648-30-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 355.2°Cat760mmHg
• Flash Point: 168.6°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 3.19E-05mmHg at 25°C
• Refractive Index: 1.526
• PKA: 9.98±0.60(Predicted)
• CAS DataBase Reference: 2-carbomethoxy-3-(4-fluorophenyl)nortropane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-carbomethoxy-3-(4-fluorophenyl)nortropane(127648-30-0)
• EPA Substance Registry System: 2-carbomethoxy-3-(4-fluorophenyl)nortropane(127648-30-0)

Safety Data

• Hazardous Substances Data: 127648-30-0(Hazardous Substances Data)

Usage

Chemical Properties

Colourless to yellowish solid

InChI:InChI=1/C15H18FNO2/c1-19-15(18)14-12(8-11-6-7-13(14)17-11)9-2-4-10(16)5-3-9/h2-5,11-14,17H,6-8H2,1H3/t11?,12?,13-,14?/m1/s1

Upstream product

• 484-93-5 ecgonidine 
• 481-37-8 ecgonine 
• 50373-10-9 methyl ecgonidine 
• 50-36-2 Cocaine 
• 352-13-6 4-flourophenylmagnesium bromide 
• 50370-59-7 2β-carbomethoxy-3β-(4-fluorophenyl)tropane 
• 303733-95-1 N-(2,2,2-trichloroethylcarbamoyl)-2β-carbomethoxy-3β-(4'-fluorophenyl)nortropane 

Downstream Products

• 189818-58-4 N-[2-(3'-N'-propyl-(1R-3β-(4-fluorophenyl)-2β-methoxycarbonyltropane))((2-((triphenylmethyl)thio)ethyl)amino)acetyl]-2-aminoethanethiol 
• 127627-50-3 2β-carbomethoxy-3β-(4-fluorophenyl)-8-propylnortropane 
• 1179817-57-2 methyl 8-(((1S,2S)-2-(fluoromethyl)cyclopropyl)methyl)-3-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 1179817-52-7 methyl 8-(((1R,2R)-2-(fluoromethyl)cyclopropyl)methyl)-3-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 1179817-48-1 methyl 8-(4-fluorobut-2-yn-1-yl)-3-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 850888-42-5 (1R)-2β-[(3,4-methylenedioxy)phenoxy]methyl-3β-(4-fluorophenyl)-8-(4-methyl benzenesulfonyl)tropane 
• 850888-41-4 (1R)-2β-hydroxymethyl-3β-(4-fluorophenyl)-8-(4-methyl benzenesulfonyl)tropane 
• 850888-40-3 (1R)-2β-carbomethoxy-3β-(4-fluorophenyl)-8-(4-methyl benzenesulfonyl)tropane 
• 127648-29-7 2β-carbomethoxy-3β-(4-fluorophenyl)-8-allylnortropane 

Relevant articles and documents

3alpha-(4-Substituted phenyl)nortropane-2beta-carboxylic acid methyl esters show selective binding at the norepinephrine transporter.

A series of 3alpha-(4-substituted)nortropane-2beta-carboxylic acid methyl esters was synthesized and evaluated for the ability to inhibit radioligand binding at the dopamine, serotonin, and norepinephrine transporters. 3alpha-(4-Methylphenyl)nortropane-2beta-carboxylic acid methyl ester (4c) was found to be selective and highly potent for the norepinephrine transporter (NET) relative to the dopamine and serotonin transporters.

BOLAAMPHIPHILIC COMPOUNDS, COMPOSITIONS AND USES THEREOF

Bolaamphiphilic compounds are provided according to formula (I); where HG1, HG2 and L1 are as defined herein. Provided bolaamphiphilic compounds and the pharmaceutical compositions thereof are useful for delivering GDNF or NGF into animal or human brain.

Synthesis, structural identification, and ligand binding of tropane ring analogs of paroxetine and an unexpected aza-bicyclo[3.2.2]nonane rearrangement product

The structural requirements for high affinity at the serotonin transporter (5-HTT) have been investigated through the preparation of rigid paroxetine analogs. Tropane-derived analogs (4a-i) of paroxetine (2) were designed and synthesized as potential inhibitors of serotonin reuptake based on the structural and biological similarity between the two compound classes. Overall, the affinity of tropane-derived analogs at the 5-HTT was found to be at least an order of magnitude lower than that of paroxetine and ranged from 2-400 nM. The reduced affinity at the 5-HTT may be attributed to the inability of the rigid tropane-derived analogs to adopt conformations favored by the 5-HTT. Within the series of tropane analogs, the 2β,3β- and 2β,3α-isomers, 4a and 4d, were the most potent at the DAT and NET and are also significantly more potent than paroxetine (2) suggesting that their reduced conformational flexibility maximizes residence time in conformations favored by these transporters. Examination of the previously published preparation and structural assignment of 4a by additional NMR and X-ray crystallographic data has established that nucleophilic addition to the intermediate 2β- methanesulfonyloxymethyl-3β-(4-fluorophenyl)tropane unexpectedly provided the aza-bicyclo[3.2.2]nonane derivative 10a.