title: 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).
abstract: 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. Copyright © 2016 The Authors. Drug Testing and Analysis Published by John Wiley & Sons Ltd.
authors.affiliation: Department of Clinical Biochemistry, North Denmark Regional Hospital (Aalborg University), Hjørring, Denmark.
authors.forename: Torben
authors.initials: T
authors.lastname: Breindahl
authors.affiliation: National Addiction Centre, Institute of Psychiatry, Psychology & Neuroscience, King's College London, London, United Kingdom.
authors.forename: Andreas
authors.initials: A
authors.lastname: Kimergård
authors.affiliation: Section for Forensic Chemistry, Department of Forensic Medicine, Aarhus University, Aarhus, Denmark.
authors.forename: Mette Findal
authors.initials: MF
authors.lastname: Andreasen
authors.affiliation: Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Copenhagen, Denmark.
authors.forename: Daniel Sejer
authors.initials: DS
authors.lastname: Pedersen
mesh_terms: D000701:Analgesics, Opioid / Q000737:chemistry*; D002853:Chromatography, Liquid; D015198:Designer Drugs / Q000737:chemistry*; D005283:Fentanyl / Q000031:analogs & derivatives*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D011619:Psychotropic Drugs / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013055:Spectrophotometry, Infrared
chemical_list: D000701:Analgesics, Opioid; D015198:Designer Drugs; D011619:Psychotropic Drugs; D005283:Fentanyl
keywords: acrylfentanyl; acryloylfentanyl; fentanyl analogue; identification; new psychoactive substances; seizure