Identification of illegal opioids using NMR

Novel psychoactive substances (NPS) include synthetic cannabinoids, novel stimulants, and synthetic opioids, among others. Often, these drugs are sold online as other items, such as herbal blends or bath salts to avoid detection and seizure by authorities.

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In recent years, the number of NPS introduced into the illicit market has reached alarming levels, in particular the synthetic opioids fentanyl and its derivatives. This increase in availability has led to a surge in the abuse of this narcotic, coupled with the fact that it is often cheaper than heroin.

Fentanyl is 80–100 times stronger than morphine, and its fluorinated derivatives have been found to have increased psychotropic effects. Since 2012, furanylfentanyl analogue has become more widely available and has been responsible for 30 deaths in the USA and Europe since 2015. Therefore, it is crucial that seized products can be fully characterized to identify known and emerging NPS.

A recent study, performed by Scientists at Sapienza University of Rome, Italy, has confirmed the presence of a new fentanyl derivative, 4-fluoro-furnaylfentanyl, in a seized NPS sample. This characterization was achieved by a combination of analytical techniques, including nuclear magnetic resonance (NMR).

Preliminary analysis of the unknown powder was performed by infrared (IR) spectroscopy. The obtained spectrum showed a 55% correspondence with fentanyl, indicating a fentanyl derivative, as well as the presence of mannitol, which is frequently used as a diluent in powder formulations.

Next, Raman spectroscopy was performed, and the spectrum compared with known fentanyl analogues. Some bands were found to be indicative of fluoro-furanylfentanyl, supporting the IR analysis of the presence of a fentanyl derivative.

Gas chromatography-mass spectrometry (GC-MS) was used to elucidate further information. The mass spectrum of the chromatographic peak at retention time 25.8 minutes was compared MS compound libraries and had a strong match with fluoro-furanylfentanyl. Further analysis with liquid chromatography high-resolution MS/MS (LC–HRMS/MS) also confirmed a match with fluoro-furanylfentanyl.

These analytical techniques provided valuable information, but none were able to determine the exact molecular structure of the fentanyl analogue, in particular the position of the fluorine. Therefore, NMR was performed to obtain this information.

One-dimensional 1H NMR and two-dimensional homonuclear total correlation spectroscopy (1H-1H TOCSY) and heteronuclear single-quantum correlation spectroscopy (1H-13C HSQC) were performed using a Bruker BioSpin AVANCE III spectrometer. These data were able to provide a definitive structure of the compound and identify the fluorine is position 4 of the fluorophenyl moiety of fluoro-furanylfentanyl, a new NPS.

While all the analytical techniques used in this study were able to offer useful information about the seized, unknown powder, NMR proved to be the most valuable technique as it was able to provide a full structural characterization.

These data have been reported to the national early warning system (NEWS) and the European Monitoring Center for Drugs and Drug Addiction (EMCDDA) to aid the identification of 4-fluoro-furanyl fentanyl, as well as differentiation from other fentanyl derivatives.

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Reference

  1. Vincenti, F., et al. (2020). Multi-Analytical Characterization of 4-Fluoro-Furanyl Fentanyl in a Drug Seizure. Forensic Chemistry. https://doi.org/10.1016/j.forc.2020.100283.

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Last updated: Jul 7, 2022 at 3:48 AM

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