Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review

Armenian, Patil; Vo, Kathy T.; Barr‐Walker, Jill; Lynch, Kara L.

doi:10.1016/j.neuropharm.2017.10.016

Cited by 540 publications

(469 citation statements)

References 112 publications

(126 reference statements)

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“…Fentanyl is a synthetic opioid approved by the FDA as an analgesic and anesthetic, but licit and illicit fentanyl analogs end up on the drug market through theft, fraudulent prescriptions and illicit distribution by patients, doctors, and pharmacists . Since 2013, fentanyl and fentanyl analogs have become increasingly common adulterants in heroin seizures, and their incredible efficacy for binding to opioid receptors in the body has caused accidental overdoses in almost every state . According to the 2017 National Laboratory Forensic Information System (NFLIS), more than 56,000 fentanyl drug reports were filed the year before by local and state forensic laboratories…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The characterization of isobaric product ions of fentanyl using multi‐stage mass spectrometry, high‐resolution mass spectrometry and isotopic labeling

Davidson

Sasiene

Jackson

2020

Drug Testing and Analysis

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This study uses a combination of multi‐stage mass spectrometry (MSn), accurate mass measurements – with high‐resolution mass spectrometry (HRMS) – and isotopic labeling to characterize the fragmentation behavior of fentanyl and 4‐ANPP. By understanding the fragmentation behavior of fentanyl and its analogs in more detail, toxicologists and seized drug analysts will be better poised to identify new and emerging fentalogs, which are increasingly common and deadly adulterants in the growing opioid crisis. Throughout the literature the product ion at m/z 188 is often the most abundant fragment in the mass spectrometric analysis of fentanyl and fentanyl analogs, and this fragment is used for both qualitative and quantitative determinations. Our work shows there are at least three different structures for the isobaric fentanyl product ions at m/z 188, and they each form and fragment via different pathways. The development of fragmentation mechanisms to explain the observed fragmentation pathways of fentanyl and its main precursor 4‐ANPP helps contribute to the advancement of knowledge about fentanyl fragmentation and could provide important information for the identification of future fentanyl analogs.

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Section: Introductionmentioning

confidence: 99%

“…Whereas fentanyl and its synthetic precursors are Schedule II narcotics, the impact on public health has led fentanyl analogs such as α‐methylfentanyl, 3‐methylfentanyl, acetylfentanyl, butyryl fentanyl, and β‐hydroxythiofentanyl to be listed as Schedule I narcotics . Figure shows the generic chemical structure of fentanyl analogs.…”

Section: Introductionmentioning

confidence: 99%

The characterization of isobaric product ions of fentanyl using multi‐stage mass spectrometry, high‐resolution mass spectrometry and isotopic labeling

Davidson

Sasiene

Jackson

2020

Drug Testing and Analysis

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“…3 Furthermore, since the 1960s, a number of fentanyl analogues have been synthesised and investigated as potential pharmaceuticals through modifications of the structure to retain the analgesic effects of fentanyl but with variations in potency and activity, including adverse effects. [5][6][7][8][9] Cyclopropylfentanyl and crotonylfentanyl are 2 compounds with the same empirical formula which are analogues of fentanyl and belong to the 4-anilidopiperidine structural class. 3,4 From 2009 to 2016, 18 fentanyl analogues were detected in Europe -8 of which were reported for the first time in 2016.…”

mentioning

confidence: 99%

The analytical challenges of cyclopropylfentanyl and crotonylfentanyl: An approach for toxicological analysis

Maher¹,

Elliott²,

George³

2018

Drug Testing and Analysis

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New psychoactive substances (NPS) are increasingly being seen in forensic casework globally and encompass a number of types of drugs including "designer opioids", especially fentanyl analogues, which are of particular concern due to their high potency and significant risk of toxicity. They are often sold as heroin or mixed with other illicit drugs and therefore users may be unaware they are taking such hazardous compounds. Two fentanyl analogues that have recently been detected are cyclopropylfentanyl and crotonylfentanyl. In order to accurately determine the prevalence of such compounds in clinical and forensic casework, including potential toxicity, they need to be correctly identified using definitive and defensible techniques. Cyclopropylfentanyl and crotonylfentanyl are structural isomers, and it has previously been highlighted that these 2 compounds are analytically difficult to specifically identify owing to their similarity in structure and chromatographic behaviour. To further investigate in an attempt to overcome this problem, analysis of certified reference material using high performance liquid chromatography with diode array UV detection (HPLC-DAD), liquid chromatography-tandem mass spectrometry (LC-MS/MS), and liquid chromatography-quadrupole time-of-flight-mass spectrometry (LC-QToF-MS) has been performed. Whilst the compounds were shown to have an identical mass-spectral fragmentation pattern, they had different UV spectra. This was coupled with a discernible difference in retention time with the HPLC conditions applied, allowing differentiation of the 2 compounds. Using this approach, cyclopropylfentanyl was positively identified and subsequently quantified in 4 fatalities with the exclusion of crotonylfentanyl.

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“…This has raised concerns about the potential for exposure to opioids among emergency responders (e.g., law enforcement officers, fire fighters, and emergency medical service workers), who might come into contact with opioids in the course of their work [Howard and Hornsby-Myers 2018]. Continual introduction of novel synthetic opioids presents continuing challenges during the current opioid epidemic [Armenian et al 2017].…”

Section: Resultsmentioning

confidence: 99%

Evaluation of a New Hampshire law enforcement officer's unintentional occupational exposure to illicit drugs.

Chiu¹,

Hornsby-Myers²,

Trout³

2018

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Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review

Cited by 540 publications

References 112 publications

The characterization of isobaric product ions of fentanyl using multi‐stage mass spectrometry, high‐resolution mass spectrometry and isotopic labeling

The characterization of isobaric product ions of fentanyl using multi‐stage mass spectrometry, high‐resolution mass spectrometry and isotopic labeling

The analytical challenges of cyclopropylfentanyl and crotonylfentanyl: An approach for toxicological analysis

Evaluation of a New Hampshire law enforcement officer's unintentional occupational exposure to illicit drugs.

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