74163-84-1

Basic information

• Product Name: Troparil
• Synonyms: Troparil;(Exo,exo)-8-methyl-3-phenyl-8-azabicyclo(3.2.1)octane-2-carboxylic acid methyl ester;2-beta-Methoxycarbonyl-3-beta-phenyltropane;8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 8-methyl-3-phenyl-, methyl ester, (exo,exo)-;8-Azabicyclo[3.2.1]octane-2-carboxylicacid, 8-Methyl-3-phenyl-, Methyl ester, (1R,2S,3S,5S)-rel-;(–)-2β-Carbomethoxy-3β-phenyltropane,WIN 35,065-2, orβ-CPT);-2β-Carbomethoxy-3β-phenyltropane ada@tuskwei.com whatsapp;2β-Carbomethoxy-3β-phenyltropane
• CAS NO: 74163-84-1
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.34
• Mol File: 74163-84-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 350.2°C at 760 mmHg
• Flash Point: 121.3°C
• Appearance: /
• Density: 1.099g/cm³
• Vapor Pressure: 4.47E-05mmHg at 25°C
• Refractive Index: 1.54
• PKA: 9.95±0.60(Predicted)
• CAS DataBase Reference: Troparil(CAS DataBase Reference)
• NIST Chemistry Reference: Troparil(74163-84-1)
• EPA Substance Registry System: Troparil(74163-84-1)

Safety Data

• Hazardous Substances Data: 74163-84-1(Hazardous Substances Data)

Usage

Description

Troparil is a phenyltropane-based dopamine reuptake inhibitor that is derived from methylecgonidine. It is a stimulant drug used in scientific research. The most commonly used form of troparil is the tartrate salt, but the hydrochloride and naphthalenedisulfonate salts are also available, as well as the free base.

Uses

Troparil is used in scientific research into the dopamine reuptake transporter. 3H-radiolabelled forms of troparil have been used in humans and animals to map the distribution of dopamine transporters in the brain. It is also used for animal research into stimulant drugs as an alternative to cocaine which produces similar effects, but avoids the stringent licensing requirements for the use of cocaine itself.

Pharmacokinetics

Troparil is a few times more potent than cocaine as a dopamine reuptake inhibitor, but is less potent as a serotonin reuptake inhibitor, and has a duration spanning a few times longer, since the phenyl ring is directly connected to the tropane ring through a non-hydrolyzable carbon-carbon bond. The lack of an ester linkage removes the local anesthetic action from the drug, so troparil is a pure stimulant. This change in activity also makes troparil slightly less cardiotoxic than cocaine.

InChI:InChI=1/C16H21NO2/c1-17-12-8-9-14(17)15(16(18)19-2)13(10-12)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14+,15-/m0/s1

Upstream product

• 50373-10-9 (R)-(-)-anhydroecgonine methyl ester 
• 100-58-3 phenylmagnesium bromide 
• 50373-10-9 methyl ecgonidine 

Downstream Products

• 127379-27-5 methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate 
• 127279-72-5 methyl (1RS-2-endo-3-exo)-3-(2,4-dinitrophenyl)-8-methyl-8-azabicyclo<3.2.1>octane-2-carboxylate 
• 127279-73-6 methyl (1RS-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate 
• 134052-62-3 RTI 29 
• 135367-05-4 3β-(4-ethoxycarboxamidophenyl)tropane-2β-carboxylic acid methyl ester 
• 135367-07-6 3β-(4-propionylaminophenyl)tropane-2β-carboxylic acid methyl ester 
• 135367-06-5 3β-(4-acetamidophenyl)tropane-2β-carboxylic acid methyl ester 
• 135416-43-2 3β-(4-iodophenyl)tropane-2β-carboxylic acid methyl ester 
• 135367-08-7 3β-(4-bromophenyl)tropane-2β-carboxylic acid methyl ester 
• 134052-62-3 3β-(4-aminophenyl)tropane-2β-carboxylic acid methyl ester 
• 127279-73-6 3β-(4-nitrophenyl)tropane-2β-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis, radiosynthesis and first in vitro evaluation of novel PET-tracers for the dopamine transporter: [11C]IPCIT and [ 18F]FE@IPCIT

Introduction Present data indicate that merging beneficial structural elements from previously published DAT-ligands highest DAT affinity, selectivity and a suitable metabolic profile should be achieved. This combination led to the development of IPCIT and FE@IPCIT. Methods Precursor synthesis was done starting from cocaine in a six step reaction. O-[11C]-methylation was established using [11C]methyl iodide, optimized and subsequently automated. Small scale 18F-fluroroethylation as well as optimization of reaction parameters and automation were performed. Affinity and selectivity of the candidate substances were tested in standard binding experiments on human membranes. Metabolic stability and blood-brain-barrier (BBB) penetration were determined. Results Precursor compound, IPCITacid, and reference compounds, IPCIT and FE@IPCIT, were obtained in 4.9%, 12.7% and 4.1% yield, respectively. Automated radiosynthesis of [11C]IPCIT yielded 1.9 ± 0.7 GBq (12.5 ± 4%, corrected for decay). Optimum parameters for 18F-fluoroethylation were 110 C for 15 min under TBAH catalysis, yielding 67 ± 16% radiochemical incorporation. Affinity was determined as 1.7 ± 0.6 nM for IPCIT, 1.3 ± 0.2 nM for FE@IPCIT and 37 ± 13 nM for the precursor molecule, IPCIT-acid. Results from in vitro and in silico evaluations revealed high stability but also high lipophilicity. Conclusion Present data indicate high affinity and stability of both IPCIT and FE@IPCIT. Radiolabelling, optimization of reaction parameters and automation succeeded. On the other hand, data concerning BBB-penetration are not promising.

Compounds affecting the central nevous system.4. 3B-phenyltropane-2-carboxylic esters and analogs

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