Psilocin - The "real deal" or an extraction byproduct.

Summary

During routine chemical identification of illicit drugs, scientists discovered that 4-acetoxy-DMT can transform into psilocin when exposed to certain bases during sample preparation. Gas chromatography-mass spectrometry analysis revealed this conversion happens more readily with stronger bases. Thermal gravimetric analysis confirmed the compound remains stable at high temperatures, proving the change occurs during pre-testing chemical processes rather than heating.

Abstract

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.

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