Potential affinity labels for the opiate receptor based on fentanyl and related compounds

Maryanoff, Bruce E.; Simon, Eric J.; Gioannini, Theresa L.; Gorissen, H.

doi:10.1021/jm00350a006

Cited by 33 publications

(19 citation statements)

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“…Compounds equal in molecular structure to acrylfentanyl have previously been reported in the literature for opiate receptor affinity after synthesis, [36] as a theoretical derivative in mathematic modelling for drug design, [37] and for in vivo activity in mice after custom synthesis. [38] In the latter study, with the use of mouse hot plate tests, it was shown that acrylfentanyl was more potent than fentanyl and had a longer duration of action.…”

Section: Previous Studiesmentioning

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: Previous Studiesmentioning

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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“…A number of fentanyl derivatives ( Figure 3) have been synthesized (42). These compounds were generally unsuccessful as affinity labels, although the diazoketone 3 and the arylazide 5 appeared upon photolysis to produce a moderate irreversible inhibition of [3H]naloxone binding to opioid receptors.…”

Section: Photoaffinity Labelsmentioning

confidence: 99%

Affinity Labels for Opioid Receptors

Takemori

Portoghese

1985

Annu. Rev. Pharmacol. Toxicol.

103

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“…The clinical relevance of in vitro studies at the human opioid receptors cannot be overlooked. Over the past several decades, fentalogs have been pharmacologically characterized primarily in rodent models 24–39 . Much of the fentalog data collected in this area is represented by in vivo experiments in which pharmacokinetic parameters make comparative evaluation difficult.…”

Section: Introductionmentioning

confidence: 99%

In vitro pharmacology of fentanyl analogs at the human mu opioid receptor and their spectroscopic analysis

Hassanien

Bassman

Naccarato

et al. 2020

Drug Testing and Analysis

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Opioids are widely misused and account for almost half of overdose deaths in the United States. The cost in terms of lives, health care, and lost productivity is significant and has been declared a national crisis. Fentanyl is a highly potent mu opioid receptor (MOR) agonist and plays a significant role in the current opioid epidemic; fentanyl and its analogs (fentalogs) are increasingly becoming one of the biggest dangers in the opioid crisis. The availability of fentalogs in the illicit market is thought to play a significant role in the recent increase in opioid‐related deaths. Although there is both rodent homolog in vivo and in vitro data for some fentalogs, prior to this publication very little was known about the pharmacology of many of these illicit compounds at the human MOR (hMOR). Using gas chromatography–mass spectrometry, nuclear magnetic resonance spectroscopy, and in vitro assays, this study describes the spectral and pharmacological properties of 34 fentalogs. The reported spectra and chemical data will allow for easy identification of novel fentalogs in unknown or mixed samples. Taken together these data are useful for law enforcement and clinical workers as they will aid in the identification of fentalogs in unknown samples and can potentially be used to predict physiological effects after exposure.

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Potential affinity labels for the opiate receptor based on fentanyl and related compounds

Cited by 33 publications

References 0 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)

Affinity Labels for Opioid Receptors

In vitro pharmacology of fentanyl analogs at the human mu opioid receptor and their spectroscopic analysis

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