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Tropane Ethyl Esters in Illicit Cocaine: Isolation, Detection, and Determination of New Manufacturing By-Products From the Clandestine Purification of Crude Cocaine Base With Ethanol

NCJ Number
223392
Journal
Journal of Forensic Sciences Volume: 53 Issue: 3 Dated: May 2008 Pages: 661-667
Author(s)
John F. Casale B.S.; Danielle K. Boudreau B.S.; Laura M. Jones B.S.
Date Published
May 2008
Length
7 pages
Annotation
In this research, recent authentic Peruvian cocaine base (n=114) and cocaine hydrochloride (n=46) exhibits were examined in order to determine their alkaloid and manufacturing impurity profiles through analytical and instrumental methods.
Abstract
In addition to the detection of cocaethylene, six new impurities were detected in the gas chromatographic signature profiles of these exhibits. Gas chromatographic-mass spectrometric (GC/MS) determined their identities, and they were subsequently synthesized in order to verify their structures. In addition to cocaethylene, the exhibits contained hexanoylecgonine ethyl ester, cis-cinnamoylecgonine ethyl ester, trans-cinnamoylecgonine ethyl ester, 3',4',5'-trimethoxybenzoylecgonine ethyl ester, cis-3',4',5'-trimethoxycinnamoylecgonine ethyl ester, and trans-3',4',5'-trimethoxycinnamoylecgonine ethyl ester. When present, these compounds were at quantitative levels that ranged from 8.6 x 10 with exponent -4-percent to 9.3 x 10 with exponent -1-percent relative to cocaine. Quantitative determinations were obtained from ion-pair chromatography isolation followed by gas chromatography with flame ionization detection. The quantitative determination of these homologues may enhance sample-to-sample comparisons as indicators of commonality. Peruvian cocaine base processors are known currently to use ethanol to purify cocaine-based instead of the classic potassium permanganate oxidation procedure. The use of ethanol during illicit processing promotes transesterification of the parent methyl ester alkaloids to their ethyl ester homologues or possibly ethyl esterification of their respective tropane C-2 carboxylic acids. 2 tables, 8 figures, and 10 references

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