Anhydroecgonine, methyl ester

S1 C10H15NO2 94 2,3-Dehydro-2-methoxyca rbonyltropane (anhydroecgonine methyl ester) Er 1... 

Jacob, P., III, Lewis, E.R., Elias-Baker, B.A., and Jones, R., A pyrolysis product, anhydroecgonine methyl ester (methylecgonidine) is in the urine of cocaine smokers, J. Anal. Toxicol., 14, 353-357,1990. 

The metabolic scheme of cocaine analytes in hair. (Abbreviations COC, cocaine BE, benzoylecgonine EME, ecgonine methyl ester ECG, ecgonine CE, cocaethylene NCOC, norcocaine NCE, norcocaethylene and AEME, anhydroecgonine methyl ester). 

Davies has reported the synthesis of enantiomerically enriched tropanes 42 by the rhodium(II) octanaote catalyzed reaction of various N-Boc pyrroles 40 with vinyldiazomethanes 41 bearing chiral auxiliaries <97JOC1095, 97AA107>. This overall 3+4 annulation occurs by a tandem cyclopropanatlon/Cope rearrangement and was applied by the author to the synthesis of (-)-anhydroecgonine methyl ester and (-)-ferruginine. 

The synthetic utility of this chemistry was highlighted by short syntheses of various biologically interesting tropanes (Scheme 36). T vo natural products, ferruginine (98) and anhydroecgonine methyl ester (99), have been prepared by selectively hydrogenating the appropriate [3+4] aimulation product followed by ]V-deprotection and iV-methylation. A number of 4P-aryl-3p-propanoyl tropanes, such... 

Da Costa et al. [113] developed and validated a method for the simultaneous determination of cocaine, benzoylecgonine, cocaethylene, anhydroecgonine, anhydroecgonine methyl ester, and ecgonine methyl ester in human urine using CE-ESl-MS/MS. The electrolyte was 1 mol formic acid, whereas 0.05 mol formic acid in methanol to water (1 1) was used as the composition of the coaxial sheath liquid at the ESI nozzle. LODs were 100 ng mL for cocaine and cocaethylene and 250 ng mL for the other metabolites, whereas LOQs were... 

Abuse of the stimulant cocaine (COC) is a common problem in the United States and elsewhere. The drug can be used either as the powder or as the free base (crack COC), and causes feelings of alertness and euphoria both forms of COC are powerfully addictive. The assay described here is designed to detect and quantitate parent COC, its major metabolite benzoylecgonine, and a selection of metabolites that can provide specific information about sample validity (w-hydroxybenzoylecgonine), potential toxicity (norcocaine), route of administration (anhydroecgonine methyl ester), and co-utilization with ethanol (cocaethylene). 

Keywords Cocaine, Crack, Benzoylecgonine, Norcocaine, Cocaethylene, w-Hydroxybenzoylecgonine, Anhydroecgonine methyl ester, LC-MS/MS... 

Use of crack can be specifically determined by the presence of metabolites unique to the thermal degradation that occurs when COC is smoked. Anhydroecgonine methyl ester (AEME, methyl ecgonidine) is found in individuals following crack administration a related compound, anhydroecgonine ethyl ester (AEEE,... 

Fig. 1. Chromatography of cocaine and related analytes. A 5 ng/mL standard containing all analytes and internal standards is shown. Anhydroecgonine ethyl ester (AEEE) is shown but not described in the above method because the pure compound is not commercially available. AEME anhydroecgonine methyl ester, 8E benzoylecgonine, CE cocaethylene, COC cocaine, /77-HOBE /77-hydroxybenzoylecgonine, /VC norcocaine.

They can distinguish between someone who has been smoking crack or merely snorting cocaine. When crack cocaine is smoked, some of the cocaine is converted into a pyrolysis product, methylecgonidine (anhydroecgonine methyl ester) - it is not found in normal ingestion of cocaine. 

Fandino,A.S.,Karas,M.,Toennes,S.W.,and Kauert,G. (2002) Identification of anhydroecgonine methyl ester N-oxide, a new metabolite of anhy-droecgonine methyl ester, using electrospray mass spectrometry. Journal of Mass Spectrometry, 37,525-532. 

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