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
• Article Data: 12

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

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 
• 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 
• 127279-73-6 3β-(4-nitrophenyl)tropane-2β-carboxylic acid methyl ester 
• 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 
• 208988-98-1 (1R,5S)-2β-formyl-3β-phenyltropane 
• 208989-52-0 (1R,2S,3S,5S)-8-Methyl-3-phenyl-2-((Z)-propenyl)-8-aza-bicyclo[3.2.1]octane 
• 1027576-80-2 3-((1R,2S,3S,5S)-8-Methyl-3-phenyl-8-aza-bicyclo[3.2.1]oct-2-yl)-propionaldehyde 

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.

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.