50372-80-0

Basic information

• Product Name: CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC
• Synonyms: CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC;(1r-(exo,exo))-8-methyl-3-phenyl-8-azabicyclo(3.2.1)octane-2-carboxylicacid;8-azabicyclo(3.2.1)octane-2-carboxylicacid,8-methyl-3-phenyl-,methylester,;exo))-(1r-(ex;win350650-2;CPT D-TARTRATE >94% POTENT LIGAND FOR TH E;(-)-2β-Carbomethoxy-3β-phenyltropane tartrate, WIN 35,065-2;D-CPT tartrate
• CAS NO: 50372-80-0
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 409.43
• Product Categories: Aromatics, Heterocycles, Neurochemicals, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 50372-80-0.mol

Chemical Properties

• Boiling Point: 350.2°C at 760 mmHg
• Flash Point: 121.3°C
• Appearance: white/
• Density: 1.099g/cm³
• Vapor Pressure: 4.47E-05mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: −20°C
• Solubility: H2O: soluble
• PKA: 9.95±0.60(Predicted)
• CAS DataBase Reference: CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC(CAS DataBase Reference)
• NIST Chemistry Reference: CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC(50372-80-0)
• EPA Substance Registry System: CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC(50372-80-0)

Safety Data

• WGK Germany: 3
• RTECS: CL5603110
• Hazardous Substances Data: 50372-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC is used as an intermediate in the synthesis of RTI-55 (R701010), a semi-synthetic alkaloid that is a cocaine analogue belonging to the phenyltropane group. It plays a crucial role in the development of CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC, which has potential applications in the treatment of various medical conditions.
Used in Chemical Synthesis:
CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC is also used as a building block in the synthesis of other complex organic compounds. Its unique structure and functional groups make it a valuable component in the creation of various molecules with diverse applications in different industries.

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

• 100-58-3 phenylmagnesium bromide 
• 50373-10-9 methyl ecgonidine 
• 481-37-8 ecgonine 
• 50-36-2 Cocaine 
• 53757-87-2 (1R,2S,5R)-8-Methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 
• 1336-21-6 ammonium hydroxide 
• 50373-10-9 (R)-(-)-anhydroecgonine methyl ester 

Downstream Products

• 134052-62-3 RTI 29 
• 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 
• 142764-90-7 C₁₆H₂₀⁽²⁾HNO₂ 
• 142796-70-1 C₁₆H₂₀⁽²⁾HNO₂ 
• 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 
• 50372-82-2 2β-(hydroxymethyl)-3β-phenyltropane 
• 146862-27-3 3β-phenyltropane-2β-carboxylic acid 
• 159154-19-5 2β-(3'-hydroxypropyl)-3β-phenyltropane 
• 159154-16-2 2β-(2'-(methoxycarbonyl)eth-1'-enyl)-3β-phenyltropane 
• 159154-17-3 2β-(2'-(methoxycarbonyl)ethyl)-3β-phenyltropane 
• 159154-20-8 2β-(4'-(methoxycarbonyl)but-3'-enyl)-3β-phenyltropane 
• 187829-49-8 2β-(3'-phenyl-3'-oxopropyl)-3β-phenyltropane 
• 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.

Synthesis and monoamine uptake inhibition of conformationally constrained 2β-carbomethoxy-3β-phenyl tropanes

A series of 2β-carbomethoxy-3β-phenyl tropanes with conformationally constrained nitrogen substituents were synthesized as potential selective dopamine transporter ligands. These novel compounds were examined for their monoamine uptake inhibition potency at the human dopamine transporter (hDAT), the human serotonin transporter (hSERT) and the human noradrenalin transporter (hNET), stably expressed in human embryonic kidney cells (HEK). A SAR-study was conducted to determine the contribution of extended, 4-fluorinated, conformationally constrained C4 chains at the tropane nitrogen to human monoamine transporter affinity and selectivity. The Royal Society of Chemistry 2009.

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.

AN IODINATED NEUROPROBE FOR MAPPING MONOAMINE REUPTAKE SITES

An iodinated neuroprobe is provided for mapping monoamine reuptake sites. The iodinated neuroprobe is of the formula: wherein R=a CnH2n+1 group where n=0-6, an alkenyl group, a monofluoroalkyl group including nF where n=18 or 19, or a mCnH2n+1 gro

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 and monoamine transporter affinity of 2β-carbomethoxy-3β-(2-,3- or 4-substituted) biphenyltropanes

A series of 11 novel 3β-substituted biphenyltropanes was synthesized and evaluated by selective radioligand binding assays for affinity to monoamine transporters. Both 5-HTT potency and selectivity for 5-HTT over DAT was greatest with electron withdrawing group at the 3-position. (C) 2000 Elsevier Science Ltd. All rights reserved.

Iodinated neuroprobe for mapping monoamine reuptake sites

An iodinated neuroprobe is provided for mapping monoamine reuptake sites. The iodinated neuroprobe is of the formula: STR1 wherein: R=aryl, substituted aryl, heterocyclic, CO(CH2)n Y, (CH2)n CHF2, and

Stereoselective synthesis of 2β-carbomethoxy-3β-phenyltropane derivatives. Enhanced stereoselectivity observed for the conjugate addition reaction of phenylmagnesium bromide derivatives with anhydro dichloromethane

The use of dichloromethane as a solvent for the conjugate addition reaction of preformed etheral solutions of phenylmagnesium bromide derivatives with anhydroecgonine methyl ester (2) was found to enhance the stereoselectivity of the reaction and provide the 2β-carbemethoxy-3β-phenyltropane derivatives 3a-d in high yield.

Iodinated neuroprobe for mapping monoamine reuptake sites

An iodinated neuroprobe is provided for mapping monoamine reuptake sites. The iodinated neuroprobe is of the formula: STR1 wherein R=a Cn H2n+1 group where n=0-6, an alkenyl group, a monofluoroalkyl group including n F whe