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Lesser Alkaloids of Cocaine-Bearing Plants; Part I: Nicotinoyl-, 2'-Pyrroloyl, and 2'- and 3'-Furanoylecgonine Methyl Ester: Isolation and Mass Spectral Characterization of Four New Alkaloids of South American Eythroxylum Coca Var. Coca

NCJ Number
168683
Journal
Journal of Forensic Sciences Volume: 42 Issue: 2 Dated: (March 1997) Pages: 246-255
Author(s)
J M Moore; J F Casale
Date Published
1997
Length
10 pages
Annotation
Four new trace-level alkaloids of South American Erythroxylum coca var. coca, namely, 2'- and 3'-furanoylecgonine methyl ester, nicotinoyl- and 2'-pyrroloylecgonine methyl ester, have been partially isolated and structurally characterized by electron and chemical ionization mass spectrometry and by comparison of their mass spectra and gas chromatography retention times with synthesized standards.
Abstract
Alkaloid isolation methodology included toluene extraction of the leaf, followed by dilute acid/Celite and alumina column chromatography and recrystallization. This methodology also allowed for the detection and partial characterization of an additional 125-150 new tropane alkaloids in coca leaf. From a law enforcement perspective, the interrelationship between alkaloids of the plant and their presence in the refined illicit drugs derived from those plants can have both strategic and tactical importance. This includes being able to evaluate chemicals and processes used in the extraction of the alkaloid from the plant and its eventual conversion to a refined drug. Thus, it is possible to monitor the diversion of chemicals and solvents to clandestine drug laboratories. Second, some illicit drugs are derived from plants that may be cultivated in disparate areas of the world. Knowledge of these plant alkaloids and their detection in the refined drug may allow for the determination of the latter geographic origin. Third, the detection of plant alkaloids and related compounds in illicit refined drugs is more facile if first characterized in their botanical sources. Finally, the determination of plant alkaloids in illicit drugs may allow for the chemical comparison of various drug seizures to determine if they came from the same source. 5 figures, 3 tables, and 15 references

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