Identification of a new psychoactive substance in seized material: The synthetic opioid N-phenyl-N-[1-(2-phenethyl)piperidin-4-yl]prop-2-enamide (Acrylfentanyl)

TY - JOUR

T1 - Identification of a new psychoactive substance in seized material

T2 - The synthetic opioid N-phenyl-N-[1-(2-phenethyl)piperidin-4-yl]prop-2-enamide (Acrylfentanyl)

AU - Breindahl, Torben

AU - Kimergård, Andreas

AU - Andreasen, Mette Findal

AU - Pedersen, Daniel Sejer

N1 - This article is protected by copyright. All rights reserved.

PY - 2017/3/1

Y1 - 2017/3/1

N2 - Among the new psychoactive substances (NPS) that have recently emerged on the market, many of the new synthetic opioids have shown to be particularly harmful. A new synthetic analogue of fentanyl, N-phenyl-N-[1-(2-phenethyl)piperidin-4-yl]prop-2-enamide (acrylfentanyl), was identified in powder from a seized capsule found at a forensic psychiatric ward in Denmark. Gas chromatography with mass spectrometry (GC-MS) identified a precursor to synthetic fentanyls, N-phenyl-1-(2-phenylethyl)piperidin-4-amine; however, the precursor 1-(2-phenethyl)piperidin-4-one, was not detected. Analysis of the electron impact mass spectrum of the main, unknown chromatographic peak (GC) tentatively identified an acryloyl analogue of fentanyl. Further analyses by quadrupole time-of-flight high resolution mass spectrometry (QTOF-MS), matrix-assisted laser ionization Orbitrap mass spectrometry (MALDI-Orbitrap-MS), nuclear magnetic resonance spectroscopy (NMR), and infra-red spectroscopy (IR) confirmed the presence of acrylfentanyl (also known as acryloylfentanyl). Quantitative analysis with liquid chromatography and triple quadrupole mass spectrometry (LC-MS/MS) determined the content of acrylfentanyl in the powder, equal to 88.3 mass-% acrylfentanyl hydrochloride. An impurity observed by NMR was identified as triethylamine hydrochloride. Acrylfentanyl is sold on the Internet as a ‘research chemical’. Like other synthetic fentanyls, such as acetylfentanyl, it poses a serious risk of fatal intoxication.

AB - Among the new psychoactive substances (NPS) that have recently emerged on the market, many of the new synthetic opioids have shown to be particularly harmful. A new synthetic analogue of fentanyl, N-phenyl-N-[1-(2-phenethyl)piperidin-4-yl]prop-2-enamide (acrylfentanyl), was identified in powder from a seized capsule found at a forensic psychiatric ward in Denmark. Gas chromatography with mass spectrometry (GC-MS) identified a precursor to synthetic fentanyls, N-phenyl-1-(2-phenylethyl)piperidin-4-amine; however, the precursor 1-(2-phenethyl)piperidin-4-one, was not detected. Analysis of the electron impact mass spectrum of the main, unknown chromatographic peak (GC) tentatively identified an acryloyl analogue of fentanyl. Further analyses by quadrupole time-of-flight high resolution mass spectrometry (QTOF-MS), matrix-assisted laser ionization Orbitrap mass spectrometry (MALDI-Orbitrap-MS), nuclear magnetic resonance spectroscopy (NMR), and infra-red spectroscopy (IR) confirmed the presence of acrylfentanyl (also known as acryloylfentanyl). Quantitative analysis with liquid chromatography and triple quadrupole mass spectrometry (LC-MS/MS) determined the content of acrylfentanyl in the powder, equal to 88.3 mass-% acrylfentanyl hydrochloride. An impurity observed by NMR was identified as triethylamine hydrochloride. Acrylfentanyl is sold on the Internet as a ‘research chemical’. Like other synthetic fentanyls, such as acetylfentanyl, it poses a serious risk of fatal intoxication.

U2 - 10.1002/dta.2046

DO - 10.1002/dta.2046

M3 - Journal article

C2 - 27476446

SN - 1942-7603

VL - 9

SP - 415

EP - 422

JO - Drug Testing and Analysis

JF - Drug Testing and Analysis

IS - 3

ER -