Characterization and differentiation of cyclopropylfentanyl from E-crotonylfentanyl, Z-crotonylfentanyl, and 3-butenylfentanyl

Recently, a sample containing cyclopropylfentanyl was analyzed at this laboratory. Cyclopropylfentanyl began to appear in the United States' illicit drug markets in 2017. Unfortunately, cyclopropylfentanyl presents an analytical challenge due to its mass spectrum being almost identical to that...

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Bibliographic Details
Published inScience & justice Vol. 59; no. 1; pp. 67 - 74
Main Authors Mallette, Jennifer R., Casale, John F., Hays, Patrick A.
Format Journal Article
LanguageEnglish
Published England Elsevier B.V 01.01.2019
Subjects
Analgesics, Opioid - analysis
Chromatography
Crotonylfentanyl
Cyclopropylfentanyl
Fentanyl - analogs & derivatives
Fentanyl - analysis
Forensic chemistry
Gas Chromatography-Mass Spectrometry
Illicit Drugs - analysis
Isomerism
Magnetic Resonance Spectroscopy
Spectrometry
Spectroscopy, Fourier Transform Infrared
Spectrometry
Crotonylfentanyl
Cyclopropylfentanyl
Forensic chemistry
Chromatography
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Summary:Recently, a sample containing cyclopropylfentanyl was analyzed at this laboratory. Cyclopropylfentanyl began to appear in the United States' illicit drug markets in 2017. Unfortunately, cyclopropylfentanyl presents an analytical challenge due to its mass spectrum being almost identical to that of crotonylfentanyl. There are two possible isomers of crotonylfentanyl, Z- and E- crotonylfentanyl. In order to provide sufficient analytical data to distinguish the two isomers of crotonylfentanyl and cyclopropylfentanyl, crotonylfentanyl was synthesized and fully characterized. Each isomer was analyzed via nuclear magnetic resonance spectroscopy, gas chromatography–mass spectrometry, and Fourier transform infrared spectroscopy. During the synthesis of crotonylfentanyl, an unknown compound was formed. The identification of this compound and the analytical characterization of the two isomers of crotonylfentanyl are presented. Through the comparison of these compounds, it was confirmed that cyclopropylfentanyl can be differentiated from crotonylfentanyl. •Fentanyl-related compounds are often difficult to identify.•Isomers of crotonyfentanyl were synthesized for full characterization.•The isomers of crotonylfentanyl are differentiated from cyclopropylfentanyl.
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ISSN:1355-0306
1876-4452
DOI:10.1016/j.scijus.2018.07.005