Neutral Heroin Impurities from Tetrahydrobenzylisoquinoline Alkaloids
Laudanosine, reticuline, codamine, and laudanine are members of the tetrahydrobenzylisoquinoline family of natural products. These alkaloids are present in the opium poppy, Papaver somniferum, and are subsequently found as impurities in clandestinely processed morphine. Morphine is then synthesized...
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Published in | Journal of forensic sciences Vol. 51; no. 2; pp. 308 - 320 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
Malden, USA
Blackwell Publishing Inc
01.03.2006
Wiley Subscription Services, Inc |
Subjects | |
Online Access | Get full text |
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Summary: | Laudanosine, reticuline, codamine, and laudanine are members of the tetrahydrobenzylisoquinoline family of natural products. These alkaloids are present in the opium poppy, Papaver somniferum, and are subsequently found as impurities in clandestinely processed morphine. Morphine is then synthesized to heroin using hot acetic anhydride. During the course of this study, it was determined that these four tetrahydrobenzylisoquinolines undergo degradation to a series of 18 neutral impurities when subjected to hot acetic anhydride. Based on the degradation pathway, these new impurities were categorized into two sets of impurities called the C1‐acetates compounds and the stilbene compounds. Synthesis, isolation, and structural elucidation information is provided for the tetrahydrobenzylisoquinoline alkaloids, and the new neutral impurities have been studied. Several hundred authentic heroin samples were analyzed using an established heroin signature program method. This methodology features the detection of trace neutral impurities present in heroin samples. It was determined that all 18 new impurities were detected in various quantities in four different types of heroin samples. Analytical results featuring these new impurities are reported for South American‐, Southwest Asian‐, Mexican‐, and Southeast Asian‐type heroin samples. These new impurities, coupled with other established forensic markers, enhance the ability to classify illicit heroin samples. |
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Bibliography: | ArticleID:JFO57 istex:F64FF3DD067C179DFBBE8D98A55841E08752F984 ark:/67375/WNG-SF9N16H1-M ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-1198 1556-4029 |
DOI: | 10.1111/j.1556-4029.2006.00057.x |