150583-22-5

Upstream product

• 50370-59-7 2β-carbomethoxy-3β-(4-fluorophenyl)tropane 

Downstream Products

• 201472-86-8 (1R,2S,3S,5S)-2-(Benzo[1,3]dioxol-5-yloxymethyl)-3-(4-fluoro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octane 
• 217438-61-4 2β-<(4,7-dithiaoctanoyloxy)methyl>-3β-(4-fluorophenyl)tropane 
• 208989-00-8 (1R,5S)-3β-(p-fluorophenyl)-2β-formyltropane 

Relevant academic research and scientific papers

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.

Synthesis and Monoamine Transporter Binding of 2-(Diarylmethoxymethyl)-3β-aryltropane Derivatives

3β-Aryltropane analogues wherein the 2-position was substituted with various diarylmethoxyalkyl groups were synthesized and evaluated for binding at the dopamine transporter (DAT), serotonin transporter (SERT), norepinephrine transporter (NET), and muscar

Tropane-derivatives, their preparation and use

Compounds of formula (a), (b), (c), or (d), or any mixture thereof, or a pharmaceutically-acceptable salt thereof; wherein R is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or 2-hydroxyethyl; R3 is —CH2—X—R′, wherei

Synthesis and ligand binding of tropane ring analogues of paroxetine

(3S,4R)-4-(4-Fluoropheny)-3-[[3,4- (methylenedioxy)phenoxy]methyl]piperidine [(3S,9R)-3, paroxetine] is a selective serotonin reuptake inhibitor (SSRI) used as an antidepressant in humans. In previous studies, we reported that certain (1R)-3β-(substituted

Synthesis and biological properties of new 2β-alkyl- and 2β-aryl-3- (substituted phenyl)tropane derivatives: Stereochemical effect of C-3 on affinity and selectivity for neuronal dopamine and serotonin transporters

In our efforts to identify molecules that might act as cocaine antagonists or cocaine partial agonists, we have been involved in efforts to further elucidate the nature of cocaine's binding to the dopamine transporter (DAT) through strategic modifications

Tropane-2-aldoxime derivatives as nevro transmitter reuptake inhibitors

The present invention discloses compounds of the formula, STR1 any mixture thereof, or a pharmaceutically acceptable salt thereof; wherein R, R3, and R4 each have the meanings set forth in the specification. The compounds possess valuable pharmaceutical properties as monoamine neurotransmitter, i.e dopamine, serotonin, noradrenalin, reuptake inhibitors.