NCJ Number
213743
Journal
Journal of Forensic Sciences Volume: 51 Issue: 2 Dated: March 2006 Pages: 308-320
Date Published
March 2006
Length
13 pages
Annotation
This paper reports on the preparation and purification of tetrahydrobenzylisoquinoline compounds--a family of natural products (alkaloids) present in the opium poppy and subsequently present as impurities in illegally processed morphine--the identification of their corresponding neutral impurities, and the forensic trends of these neutral compounds from the analysis of heroin samples produced from the synthesis of morphine.
Abstract
The study determined that four members of the tetrahydrobenzylisoquinoline family--laudanosine, reticuline, codamine, and laudanine--undergo degradation to a series of 18 neutral impurities when subjected to hot acetic anhydride, which is used in the process of synthesizing morphine to heroin. Based on the degradation pathway, these new impurities were classified into two sets of impurities called the C1-acetates compounds and the stilbene compounds. Information on the synthesis, isolation, and structural profiling for the tetrahydrobenzylisoquinoline alkaloids is provided. All 18 new impurities were detected in various quantities in four types of heroin samples. Analytical results for the impurities are reported for South American-type, Southwest Asian-type, Mexican-type, and Southeast Asian-type heroin samples. These new impurities, coupled with other established forensic markers, improve the ability of forensic analysts to classify illicit heroin samples. The study analyzed several hundred authentic heroin samples with an established heroin signature program. It used high-performance liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, NMR analysis, and high-resolution mass spectrometry. 1 table, 10 figures, and 19 references