Nicotinamid‐2′.3′‐didesoxy‐ribofuranosyl‐adenosinpyrophosphat

Synthesis of sulfonamide-conjugated glycosyl-amino acid building blocks.

Protecting Groups at the Secondary Positions of Carbohydrates

Most illicit drug casework samples at the Israel Police National Drug Laboratory are found to be mixtures of substances. Some are a mixture of an illicit drug with fillers, and others may contain more than one illicit drug. This study was triggered by a routine gas chromatography‐mass spectrometry (GC‐MS) analysis of an unusual casework sample. The sample chromatogram showed a mixture of two illicit drugs, 4‐acetoxy‐DMT and psilocin. Considering the two substances’ similar skeletal structure, the authors wondered whether the sample was indeed a mixture of the two substances, or whether perhaps 4‐acetoxy‐DMT was hydrolyzed to psilocin during the analysis. This study hypothesized that indeed the base used in the pre‐injection sample preparation hydrolyzed the ester group on the 4‐acetoxy‐DMT yielding a hydroxide group. This was tested using several concentrations of ammonium hydroxide and two additional bases – pyridine (a weak base) and sodium hydroxide (a strong base). Results showed that media with a higher pH (induced by the stronger base) yielded a higher psilocin to 4‐acetoxy‐DMT ratio which is compatible with degradation of 4‐acetoxy‐DMT. This study also explored the possibility that psilocin was a byproduct of thermal decomposition of 4‐acetoxy‐DMT and found it thermally stable in the temperature of the GC injection port (200°C). The 4‐acetoxy‐DMT case demonstrates how pre‐injection laboratory procedures can inadvertently modify casework samples. Caution is clearly advisable in selecting reagents and processes in general, and specifically in the case of GC‐MS pre‐injection procedures conducted to analyze substances like the ones in the present study.

Psilocin – The “real deal” or an extraction byproduct

Acidic deacetylation of sugar acetates

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Acidic deacetylation of sugar acetates