136794-87-1

Usage

Uses

Used in Pharmaceutical Industry:
NOR-BETA-CIT is used as a research chemical for studying the serotonin (5-HT) transporter. Its role in inhibiting the transporter makes it a valuable tool in understanding the mechanisms of serotonin regulation and its implications in various neurological and psychiatric disorders.
Used in Medical Research:
NOR-BETA-CIT is used as a diagnostic and research tool in medical research, particularly in the study of serotonin-related disorders such as depression, anxiety, and obsessive-compulsive disorder. Its ability to inhibit the serotonin transporter can help researchers gain insights into the pathophysiology of these conditions and develop potential therapeutic strategies.
Used in Drug Development:
NOR-BETA-CIT is used as a lead compound in the development of new drugs targeting the serotonin (5-HT) transporter. Its inhibitory properties can be leveraged to create novel therapeutic agents for the treatment of various psychiatric and neurological disorders, potentially improving the efficacy and safety of existing treatments.

InChI:InChI=1/C15H18INO2/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

Upstream product

• 53898-68-3 (-)-Win 35981 
• 135416-43-2 (1R,2S,3S,5S)-3-(4-Iodo-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 
• 156496-01-4 (1R,2S,3S,5S)-3-(4-Iodo-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester 
• 17878-43-2 [4-(trimethylsilyl)phenyl]magnesium bromide 
• 50372-80-0 WIN 35,065-2 
• 131479-15-7 (1R,2S,3S,5S)-3-Phenyl-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester 
• 50373-10-9 methyl ecgonidine 
• 174224-35-2 2β-carbomethoxy-3β-(4'-trimethylsilylphenyl)tropane 

Downstream Products

• 155798-01-9 FE-beta-CIT 
• 155797-99-2 FP-beta-CIT 
• 173378-73-9 N-(3-hydroxypropyl)-2β-carbomethoxy-3β-(4'-iodophenyl)nortropane 
• 156496-01-4 (1R,2S,3S,5S)-3-(4-Iodo-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester 
• 848469-54-5 (1R,2S,3S,5S)-3-(4-Thiophen-2-yl-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester 
• 848469-63-6 (1R,2S,3S,5S)-3-(4-Thiophen-3-yl-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester 
• 186381-69-1 [¹⁸F]FP-CIT 

Relevant academic research and scientific papers

Synthesis and monoamine transporter affinity of new 2β-carbomethoxy- 3β-[aryl or heteroaryl]phenyltropanes

A series of 16 new 2β-carbomethoxy-3β-[aryl or heteroaryl]phenyltropane derivatives was synthesized and evaluated for binding to monoamine transporters. Most of the compounds exhibited nanomolar affinity for the serotonin transporter (SERT). Four compound

Synthesis and monoamine transporter affinity of new 2β-carbomethoxy- 3β-[4-(substituted thiophenyl)]phenyltropanes: Discovery of a selective SERT antagonist with picomolar potency

Preparation of cocaine analogues has been aimed largely at development of stable compounds with high affinity and selectivity for the dopamine transporter (DAT). We now report the synthesis and monoamine transporter affinity of 10 new 2β-carbomethoxy-3β-[

Fluoralkenyl nortropanes

Provided are compounds of the following formula: wherein R is C2-C6 mono- or multi-unsaturated hydrocarbon having one or more ethylene, acetylene or allene groups, A is 18 or 19, and X is H or halogen. The compounds of the invention bind to dopamine transporter with high affinity and selectivity and are thus useful as diagnostic and therapeutic agents for diseases associated with dopamine transporter dysfunction. The radiolabeled compounds are useful as imaging agents for visualizing the location and density of dopamine transporter by PET imaging.

Synthesis and biological evaluation of a series of novel N- or O-fluoroalkyl derivatives of tropane: Potential positron emission tomography (PET) imaging agents for the dopamine transporter

A series of novel fluoroalkyl-containing tropane derivatives was synthesized, and their binding affinities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) were determined via competitive binding assays. Among these derivatives, the fluoropropyl ester of β-CIT (19), the fluoroethyl ester of β-CIT (20), the N-fluoropropyl derivative of β-CBT (12), and the fluoropropyl ester of β-CMT (18) displayed higher affinity and greater selectivity for the DAT versus SERT and NET than FP-CIT, which indicates that they are attractive candidates for the development of 18F-labeled PET imaging agents for the DAT.

Secondary amine analogues of 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid esters and N-norcocaine exhibit enhanced affinity for serotonin and norepinephrine transporters.

N-Norcocaine (2) and six N-nor-3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid esters (4a-f) were synthesized by N-demethylation of cocaine (1) and the appropriate 3 beta-(substituted phenyl)-tropane analogues (3a-f) with alpha-chloroethyl chloroformate. Radioligand binding affinities of 2 and 4a-f at the DA, 5-HT, and NE transporter were measured and compared to those of 1 and 3a-f. N-Demethylation produced relatively small effects at the DA transporter. In contrast, 4-19-fold and 2-44-fold enhanced affinity at the serotonin and norepinephrine transporter resulted from demethylation. N-Nor-3 beta-(4'-iodophenyl)tropane-2 beta-carboxylic acid methyl ester (4d) with an IC50 = 0.36 nM showed the greatest affinity for the serotonin transporter. However, N-nor-3 beta-(4'-ethylphenyl)tropane-2 beta-carboxylic acid methyl ester (4e) showed the greatest selectivity for the serotonin transporter.