Studies on Fentanyl and Related Compounds IV. Chromatographic and Spectrometric Discrimination of Fentanyl and its Derivatives

Ohta, Hikoto; Suzuki, Shinichi; Ogasawara, Kunio

doi:10.1093/jat/23.4.280

Cited by 57 publications

(52 citation statements)

References 4 publications

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“…Based on the GC‐MS data alone, we arrived at the hypothesis, that the unknown compound was the acryloyl derivative of fentanyl (acrylfentanyl). Following the EI fragmentation patterns for fentanyl and related compounds published by Ohta et al .,32 the bond cleavage points can be assigned (Figure 3). Three fragment ions for acrylfentanyl (Figure 3B) differ with 2 Da from those of fentanyl (Figure 3A): m / z 243 (base peak), m / z 200 (from the piperidine ring), and m / z 55 (from the acryloyl group).…”

Section: Resultsmentioning

confidence: 99%

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)

Breindahl

Kimergård

Andreasen

et al. 2016

Drug Testing and Analysis

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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.

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Section: Resultsmentioning

confidence: 99%

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)

Breindahl

Kimergård

Andreasen

et al. 2016

Drug Testing and Analysis

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“…Fentanyl analogues with a methyl group (e.g., α-methyl, 3-methyl, p-methyl, n-butyryl, and isobutyryl) were synthesized in accordance with previous reports [6,7,[10][11][12][13][14][15].…”

Section: Synthesis Of Fentanyl Analoguesmentioning

confidence: 98%

“…These compounds had high potential for abuse, because of their ease of synthesis and high analgesic activity. The structures of fentanyl (1) and 11 synthesized analogues (2-12) examined in this study are shown in Tables 1-4. Although there are a number of reports regarding the analgesic activities of some of these analogues [8][9][10][11][12][13][14][15], there have been only a few reports on the actually abused analogues [8]; there have been no reports on α-methylfentanyl (2), the most widely abused analogue. Furthermore, comparison of their analgesic activities with those of morphine and fentanyl was not described.…”

Section: Introductionmentioning

confidence: 99%

Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure-analgesic activity relationship for fentanyl, methyl-substituted fentanyls and other analogues

2008

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“…7) Furthermore, several discrimination methods for fentanyl and its analogues have been reported. [8][9][10][11][12][13] The structures of fentanyl, 3-methylfentanyl and α-methylfentanyl are shown in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

Studies on 1-(2-Phenethyl)-4-(N-Propionylanilino)Piperidine (Fentanyl) and Its Related Compounds: Novel Metabolites in Rat Urine Following Injection of .ALPHA.-Methylfentanyl, One of the Most Abused Typical Designer Drugs

Higashikawa

Suzuki

2008

JOURNAL OF HEALTH SCIENCE

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Although 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) is controlled by drug control laws, its slightly modified compounds, which show the same analgesic activities, cannot be controlled legally. Among these fentanyl analogues, 1-[2-(2-methylphenethyl)]-4-(N-propionylanilino)piperidine (α-methylfentanyl) is the typical and most widely abused drug and its overdose has caused a number of fatalities. Analysis of the urine of addicts has been widely performed to detect its metabolites and the unchanged compound for proof of its abuse. In this case, the metabolites detected in urine should reflect the structure of the original compound. In the present report, for clarification of α-methylfentanyl abuse, four novel metabolites, which reflect the original structure of α-methylfentanyl, were identified in rat urine. One of these was the p-hydroxy form of the aromatic ring of the α-methylfentanyl phenethyl group (mono-aromatic hydroxy α-methylfentanyl), while the second and third ones were metabolites of ω-1 or ω position hydroxypropionyl of α-methylfentanyl (mono-hydroxypropionyl α-methylfentanyl). The fourth one was a metabolite involving the p-hydroxy form of the aromatic ring of the phenethyl group and ω position of hydroxypropionyl α-methylfentanyl (di-hydroxy α-methylfentanyl). The structures of these compounds were identified by comparisons of their retention times and mass spectra obtained by gas chromatography-mass spectrometry (GC/MS) and mass chromatography of mono-and di-hydroxy α-methylfentanyl with those of the synthesized authentic compounds.

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Studies on Fentanyl and Related Compounds IV. Chromatographic and Spectrometric Discrimination of Fentanyl and its Derivatives

Cited by 57 publications

References 4 publications

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)

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)

Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure-analgesic activity relationship for fentanyl, methyl-substituted fentanyls and other analogues

Studies on 1-(2-Phenethyl)-4-(N-Propionylanilino)Piperidine (Fentanyl) and Its Related Compounds: Novel Metabolites in Rat Urine Following Injection of .ALPHA.-Methylfentanyl, One of the Most Abused Typical Designer Drugs

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