140633-58-5

Usage

Uses

Used in Pharmaceutical Industry:
8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(4-chlorophenyl)-8-methyl-, (1R,2S,3S,5S)is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Research and Development:
8-Azabicyclo[3.2.1]octane-2-carboxylic acid,
3-(4-chlorophenyl)-8-methyl-, (1R,2S,3S,5S)is also used in research and development for studying its chemical properties, reactivity, and potential interactions with other molecules. Understanding its behavior can lead to the discovery of new reactions and applications in the field of organic chemistry.
Used in Drug Synthesis:
8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(4-chlorophenyl)-8-methyl-, (1R,2S,3S,5S)serves as a key intermediate in the synthesis of RTI-113 (R701110), a 3-phenyltropane analogue that acts as a potent and selective dopamine uptake inhibitor. RTI-113 has shown promise in reducing cocaine self-administration at high occupancy of the dopamine transporter, making it a potential candidate for the development of agonist therapies for cocaine dependence.
Used in Cocaine Addiction Treatment:
As a derivative of RTI 70, 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(4-chlorophenyl)-8-methyl-, (1R,2S,3S,5S)- plays a role in the development of potential treatments for cocaine addiction. RTI 70 is a cocaine derivative that prevents cocaine and MK-801 inhibition of the nicotinic acetylcholine receptor (nAChR). The compound's ability to modulate the effects of cocaine on the nAChR makes it a valuable tool in the development of therapies for cocaine dependence.

Upstream product

• 130342-80-2 2β-carbomethoxy-3β-(4-chlorophenyl)tropane 
• 53-21-4 (-)-cocaine hydrochloride 
• 7143-09-1 methyl ecgonine 
• 50373-10-9 methyl ecgonidine 
• 873-77-8 (4-chlorphenyl)magnesium bromide 

Downstream Products

• 189950-05-8 [(1R,2R,3S,5S)-3-(4-Chloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ylmethyl]-[2-(4-methoxy-benzylsulfanyl)-ethyl]-amine 
• 189950-03-6 (1R,2S,3S,5S)-3-(4-Chloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid [2-(4-methoxy-benzylsulfanyl)-ethyl]-amide 
• 189950-09-2 N-[(1R,2R,3S,5S)-3-(4-Chloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ylmethyl]-N,N'-bis-[2-(4-methoxy-benzylsulfanyl)-ethyl]-ethane-1,2-diamine 
• 189950-07-0 2-{[(1R,2R,3S,5S)-3-(4-Chloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ylmethyl]-[2-(4-methoxy-benzylsulfanyl)-ethyl]-amino}-N-[2-(4-methoxy-benzylsulfanyl)-ethyl]-acetamide 
• 1186397-11-4 1-[3β-(4-chlorophenyl)tropane-2β-carbonylamino]-2-[1-[3β-(4-chlorophenyl)tropane-2β-carbonylaminomethyl]benzen-4-yl]ethane 
• 1186397-03-4 trans-1,4-di[3β-(4-chlorophenyl)tropane-2β-carbonylamino]cyclohexane 
• 1186397-08-9 1-[3β-(4-chlorophenyl)tropane-2β-carbonylamino]-1-[1-[3β-(4-chlorophenyl)tropane-2β-carbonylamino]benzen-4-yl]methane 
• 1186397-04-5 1-[3β-(4-chlorophenyl)tropane-2β-carbonylamino]-2-[1-[3β-(4-chlorophenyl)tropane-2β-carbonyl]piperidin-4-yl]ethane 
• 1186397-06-7 1,4-di[3β-(4-chlorophenyl)tropane-2β-carbonylamino]benzene 
• 1384179-21-8 C₁₈H₂₆Cl₂N₂ 
• 1384179-30-9 C₁₈H₂₆ClFN₂ 
• 1384179-32-1 C₁₉H₂₈Cl₂N₂ 
• 1384179-34-3 C₁₉H₂₈ClFN₂ 
• 1384179-23-0 C₂₀H₃₀Cl₂N₂O 

Relevant academic research and scientific papers

Synthesis of a β-CCT-lanthanide conjugate for binding the dopamine transporter

The development of a β-CCT-lanthanide conjugate that binds the dopamine transporter (DAT) with high affinity (Kd = 303 nM) is described. Contrast agents such as the one described herein could be used as molecular probes to directly study the binding of small molecules to receptors such as DAT via MRI, PET or SPECT. This journal is

Synthesis and evaluation of novel tropane derivatives as potential PET imaging agents for the dopamine transporter

A novel series of tropane derivatives containing a fluorinated tertiary amino or amide at the 2β position was synthesized, labeled with the positron-emitter fluorine-18 (t1/2 = 109.8 min), and tested as potential in vivo dopamine transporter (D

Synthesis and evaluation of novel N-fluoropyridyl derivatives of tropane as potential PET imaging agents for the dopamine transporter

A series of novel N-fluoropyridyl-containing tropane derivatives were synthesized and their binding affinities for the dopamine transporter (DAT), serotonin transporter (SERT) and norepinephrine (NET) were determined via competitive radioligand binding as

An extended study of dimeric phenyl tropanes

A series of dimeric phenyl tropanes consisting of two molecules of 4-chloro, 4-iodo or 4-(3-thiopheno)-phenyl tropane tethered together at the carboxylic acid moiety by a diamine or diol linker were prepared. The diamines used were a variety of linear, cyclic and aromatic diamines, while the diol tethered compounds were prepared by 'click' chemistry and contained a triazole in the linker. The new compounds were tested for binding to hDAT, hSERT and hNET. Amide linked chlorophenyl tropanes with an aromatic linker was found to be potent and selective DAT inhibitors with the best Ki value for hDAT being 6 nM. The ester linked halophenyl tropanes were more potent but displayed little selectivity in inhibition of monoamine transporter binding. Among the studied compounds an ester linker of 10 atoms between the tropane moieties gave the highest affinity. One monomeric phenyl tropane was made for comparison and was found to be less potent than the dimeric counterparts towards SERT and NET but remain highly active against DAT. Dimeric thiophenophenyl tropanes were in general found to be comparatively poor monoamine transporter binders, but significant gains of affinity of up to 45-fold could be achieved with selected dimeric chlorophenyl tropanes compared to the parent monomer. This observation implies that a secondary binding site that has affinity for phenyl tropanes, most likely the putative S2 site, is located within 13 A of the primary central S1 binding site.

Synthesis and binding affinities of 2β-(3-iodoallyloxycarbonyl)-3β-(4-substituted-aryl)tropane analogues as ligands for the dopamine transporter studies

Tropane analogues from cocaine, which is known to be one of the most reinforcing and addictive compounds, were designed, synthesized, and characterized for inhibition of presynaptic uptake of dopamine (DA) in brain. Eight new derivatives of 3β-aryl-2β-(3-iodoallyloxycarbonyl)tropanes were synthesized and tested for their potential abilities to displace [3H]2β-carbomethoxy-3β-(4-fluorophenyl)tropane (WIN 35,428) binding to the rat striatal membranes.

Synthesis, biodistribution, and primate imaging of fluorine-18 labeled 2β-carbo-1'-fluoro-2-propoxy-3β-(4-chlorophenyl)tropanes. Ligands for the imaging of dopamine transporters by positron emission tomography

2β-(R)-Carbo-1-fluoro-2-propoxy-3β-(4-chlorophenyl)tropane ((R)-FIPCT, R-6) and 2β-(S)-carbo-1-fluoro-2-propoxy-3β-(4-chlorophenyl)tropane ((S)- FIPCT, S-6) were prepared and evaluated in vitro and in vivo for dopamine transporter (DAT) selectivity and sp

Cocaine and 3β-(4'-substituted phenyl)tropane-2β-carboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter

Several 2β-carboxylic acid ester and amide analogues of cocaine and of 3β-(4'-substituted phenyl)tropane-2β-carboxylic acid were prepared. The binding affinities of these compounds, and of some previously prepared analogues, at the dopamine (DA), norepinephrine (NE), and serotonin (5-HT) transporters were determined. The phenyl esters of 3β-(4'-methylphenyl)and 3β-(4'-chlorophenyl)tropane-2β-carboxylic acid are highly potent and highly selective for the DA transporter. The isopropyl esters of 3β-(4'- chlorophenyl)- and 3β-(4'-iodophenyl)tropane-2β-carboxylic acid also possess high DA affinity and show significant DA transporter selectivity. Similarly, the phenyl and isopropyl ester analogues of cocaine are much more selective for the DA transporter than cocaine. Tertiary amide analogues of cocaine and of 3β-(4'-substituted phenyl)tropane-2β-carboxylic acids are more potent inhibitors of radioligand binding at the DA transporter than the primary and secondary amide analogues. In particular, 3β-(4'- chlorophenyl)tropane-2β-N-morpholinocarboxamide as well as the 3β-(4'- chlorophenyl)- and 3β-(4'-iodophenyl)tropane-2β-N-pyrrolidinocarboxamides possess high affinity and selectivity for the DA transporter. The N,N- dimethylamide cocaine analogue is the most selective cocaine amide derivative for the DA transporter. High correlation between the inhibition of radioligand binding and inhibition of uptake at the DA, NE, and 5-HT transporter was found for a selected group of analogues. Within this group, one compound, the isopropyl ester of 3β-(4'-iodophenyl)-tropane-2β- carboxylic acid, was found to be more potent in the inhibition of radioligand binding than in the inhibition of DA uptake. Taken together with its high potency and selectivity at the DA transporter, this suggests that this compound may be a lead in the development of a cocaine antagonist.

Probes for the cocaine receptor. Potentially irreversible ligands for the dopamine transporter

Several potentially irreversible ligands (i.e., wash-resistant binding inhibitors) for the cocaine receptor site on the dopamine transporter, derived from (-)-cocaine or 3β-phenyltropan-2β-carboxylic acid methyl ester (WIN 35,065-2), were prepared and sho