73045-45-1

Basic information

• Product Name: 8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid 8-Methyl-Ethyl Ester
• Synonyms: 8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid 8-Methyl-Ethyl Ester
• CAS NO: 73045-45-1
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.25818
• Product Categories: Metabolites & Impurities
• Mol File: 73045-45-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid 8-Methyl-Ethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid 8-Methyl-Ethyl Ester(73045-45-1)
• EPA Substance Registry System: 8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid 8-Methyl-Ethyl Ester(73045-45-1)

Safety Data

• Hazardous Substances Data: 73045-45-1(Hazardous Substances Data)

Usage

Description

8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid 8-Methyl-Ethyl Ester is a chemical intermediate derived from ecgonine (E325550) and the combustion metabolite of cocaine.

Uses

Used in Pharmaceutical Industry:
8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid 8-Methyl-Ethyl Ester is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, including drugs that target the central nervous system.
Used in Research and Development:
8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid 8-Methyl-Ethyl Ester is used as a research compound for studying the structure-activity relationships of cocaine and its analogs, as well as for developing new drugs with potential therapeutic applications.
Used in Forensic Analysis:
8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid 8-Methyl-Ethyl Ester is used as a reference compound in forensic analysis for the detection and identification of cocaine and its metabolites in biological samples.

Upstream product

• 64-17-5 ethanol 
• 50-36-2 Cocaine 
• 141-52-6 sodium ethanolate 
• 27332-39-4 cyclohepta-1,3,6-trienecarboxylic acid ethyl ester 
• 74-89-5 methylamine 
• 26902-51-2 cycloheptatriene-2-carboxylic acid 

Downstream Products

• 32399-46-5 7-(methoxycarbonyl)cycloheptatriene 
• 132725-62-3 cyclohepta-2,4,6-trienecarboxylic acid-(4-bromo-phenacyl ester) 
• 1140320-45-1 (1R,5S)-anhydroecgonin ethyl ester (2'S,3'S)-di-p-toluoyl hydrogen tartrate 
• 125710-73-8 (1R,5S)-anhydroecgonin ethyl ester (2'R,3'R)-dibenzoyl hydrogen tartrate 

Relevant articles and documents

METHOD FOR PRODUCING (1R,5S) ANHYDROECGONINE ESTER SALTS

The invention relates to a large-scale method for producing salts of (IR,5S) anhydroecgonine esters. The salt formation and selective crystallization of (IR,5S) anhydroecgonine esters with chiral acids is highly efficient in producing an enantiomer form,

Studies on hydrolytic and oxidative metabolic pathways of anhydroecgonine methyl ester (methylecgonidine) using microsomal preparations from rat organs

During smoking of cocaine-base (crack), anhydroecgonine methyl ester (AEME, methyl-ecgonidine) is formed in large amounts as a pyrolysis product of cocaine and is absorbed in the lungs. The metabolism of AEME was studied in the present investigation using microsome preparations from rat liver, lung, kidney, and brain. Potential metabolites of AEME were synthesized and used as substrate to complement the experiments. Analysis of the incubation mixtures was performed using gas chromatography - mass spectrometry and nanoelectrospray multiple-stage mass spectrometry. Screening for metabolites was focused on postulated oxidative pathways, chemical and enzymatic hydrolysis, and ethanol dependent transesterification as known from cocaine metabolism. Enzymatic hydrolysis of AEME to anhydroecgonine (AE), which was inhibited by sodium fluoride, was found in all microsomal preparations. Liver microsomes exhibited the highest activity, brain microsomes the lowest. Anhydronorecgonine methyl ester (ANEME) and anhydroecgonine methyl ester N-oxide were identified as AEME metabolites of liver and lung microsomes only. In the presence of ethanol AEME was metabolized to anhydroecgonine ethyl ester and anhydronorecgonine ethyl ester. Further metabolism of AE or ANEME was not observed. No N-hydroxy-anhydronorecgonine derivatives were found which could represent precursors of cytotoxic metabolites as known to be formed from cocaine.