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Investigation of the Use of Deuterium and Oxygen in Illicit Fentanyl Analysis Author(S): John F

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Investigation of the Use of Deuterium and Oxygen in Illicit Fentanyl Analysis Author(S): John F The author(s) shown below used Federal funding provided by the U.S. Department of Justice to prepare the following resource: Document Title: Investigation of the Use of Deuterium and Oxygen in Illicit Fentanyl Analysis Author(s): John F. Casale, Mike Lott, Jennifer R. Mallette Document Number: 255103 Date Received: August 2020 Award Number: NIJ-ONDCP IAA: 2017 DEA contract research task This resource has not been published by the U.S. Department of Justice. This resource is being made publically available through the Office of Justice Programs’ National Criminal Justice Reference Service. Opinions or points of view expressed are those of the author(s) and do not necessarily reflect the official position or policies of the U.S. Department of Justice. Investigation of the Use of Deuterium and Oxygen in Illicit Fentanyl Analysis John F. Casalea, Mike Lottb, and Jennifer R. Mallettea aU.S. Drug Enforcement Administration Special Testing and Research Laboratory Dulles, VA bIsoForensics, Inc. Salt Lake City, UT 84108 This work was conducted through an Inter-Agency Agreement dated June 28, 2017, between the Office of National Drug Control Policy (ONDCP) and the National Institute of Justice (NIJ), under DEA Contract number 15DDHQ18P00000344 with funding from the NIJ, Office of Justice Programs, U.S. Department of Justice. The opinions, findings, and conclusions or recommendations expressed in this publication/program/exhibition are those of the authors, and do not necessarily reflect those of the Department of Justice or ONDCP. This resource was prepared by the author(s) using Federal funds provided by the U.S. Department of Justice. Opinions or points of view expressed are those of the author(s) and do not necessarily reflect the official position or policies of the U.S. Department of Justice. Investigation of the Use of Deuterium and Oxygen in Illicit Fentanyl Analysis John F. Casale, Mike Lott, and Jennifer R. Mallette ABSTRACT The Drug Enforcement Administration’s (DEA) Fentanyl Signature Profiling Program (FSPP) currently analyzes illicit fentanyl samples seized from within the United States. The program utilizes impurity profiling along with stable isotope measurements to compare samples and discover unique scientific linkages that may not have been known to investigators. The method measures the carbon and nitrogen isotope ratios for illicit fentanyl and its immediate precursor, 4-ANPP. Through mass balance, the carbon isotopic signature of propionyl chloride is calculated. Despite the successful measurements of carbon and nitrogen isotope ratios, the measurements of deuterium and oxygen have not been feasible due to the high nitrogen content present in fentanyl. Traditional thermo-chemical elemental analysis isotope ratio mass spectrometry (TCEA/IRMS) methods have proven to be inaccurate for compounds containing a large proportion of nitrogen. New methods have been developed in recent years that include the use of chromium to circumvent this analytical issue. In an effort to improve the DEA FSPP’s capabilities, a method to measure deuterium and oxygen isotope ratios via the chromium implementation was successfully developed. The method was initially evaluated with the analysis of representative samples from nine kilograms of illicit fentanyl (N=63). The pooled standard deviation of δ2H for fentanyl and 4-ANPP were 1.32‰ and 1.54‰, respectively. The pooled standard deviation of δ18O for fentanyl was 0.70‰. The complete isotopic profile of fentanyl and 4-ANPP were utilized to calculate the complete isotopic profile of propionyl chloride. The deuterium measurements were found to be reproducible for fentanyl and 4-ANPP which could provide further discrimination for linking samples; however, the variability found Illicit Fentanyl Isotope Investigation 1 This resource was prepared by the author(s) using Federal funds provided by the U.S. Department of Justice. Opinions or points of view expressed are those of the author(s) and do not necessarily reflect the official position or policies of the U.S. Department of Justice. with deuterium in 4-ANPP may be a result of chemist technique. Oxygen isotope measurements in illicit fentanyl were found to be less useful due to a limited range of values and large reproducibility. Deuterium and oxygen isotope information may not be useful in linking exhibits of illicit fentanyl, however, the method may prove useful with carfentanil analyses. Illicit Fentanyl Isotope Investigation 2 This resource was prepared by the author(s) using Federal funds provided by the U.S. Department of Justice. Opinions or points of view expressed are those of the author(s) and do not necessarily reflect the official position or policies of the U.S. Department of Justice. Introduction Since 2013, the abuse of fentanyl and fentanyl-related substances has resulted in thousands of overdoses and deaths. In an effort to address the current fentanyl crisis facing the United States, the Drug Enforcement Administration has developed the Fentanyl Signature Profiling Program (FSPP). The FSPP aims to make scientific linkages between illicit fentanyl seizures based on in- depth analyses. Linkages are made by comparing illicit fentanyl signature profiles comprised of data from multiple methodologies: gas chromatography with flame-ionization detection (GC/FID), nuclear magnetic resonance spectroscopy (NMR), gas chromatography mass spectrometry (GC/MS), and 13C and 15N isotope measurements of purified fentanyl and is immediate precursor, 4-ANPP. The linkages are utilized as investigative leads on seizures where linkages were unknown or only suspected. To date, the FSPP has established 96 linkages involving 192 cases and 380 exhibits from DEA seizures of more than 1100 kilograms of fentanyl. Illicit fentanyl samples have very few organic impurities remaining, therefore, multiple methodologies must be utilized in order to gather as much information as possible in order to make a linkage. One key technique implemented currently is isotope ratio mass spectrometry (IRMS). IRMS is a popular instrumental technique utilized in many areas of research, including plant biosynthesis, climate reconstruction, and geosourcing of natural products such as emeralds and coffee. In forensic science, isotope measurements are routinely utilized for murder investigations, tracing the manufacturers of explosives, and determining the geographical origin of illicit drugs. Illicit Fentanyl Isotope Investigation 3 This resource was prepared by the author(s) using Federal funds provided by the U.S. Department of Justice. Opinions or points of view expressed are those of the author(s) and do not necessarily reflect the official position or policies of the U.S. Department of Justice. The FSPP routinely isolates illicit fentanyl from seized exhibits through a series of cleanup procedures that may include solvent extractions, acid/base extractions, or preparatory column chromatography. A portion of the isolated fentanyl is then converted to its immediate precursor, 4-ANPP (Figure 1). Aniline N N N Toluene PTSA O N imine 1-phenethyl-4-piperidone 278 203-1 NaBH4 Propionyl N Chloride N N N H3C H 3 O 4-anilino-N-phenethylpiperidone fentanyl 4-ANPP 280-2 Figure 1. Synthetic scheme to fentanyl. The 13C and 15N isotope content of the illicit fentanyl and 4-ANPP are then measured. Stable isotope measurements are expressed in the “delta” notation (δ). Delta is defined as: = 1 ( − ) or also as: Illicit Fentanyl Isotope Investigation 4 This resource was prepared by the author(s) using Federal funds provided by the U.S. Department of Justice. Opinions or points of view expressed are those of the author(s) and do not necessarily reflect the official position or policies of the U.S. Department of Justice. (‰) = 1 × 1000 ( − ) where R is the ratio of heavy to light isotopes (e.g., 13C/12C). The delta notation is expressed in per mil (‰). Using mass balance, the 13C signature of propionyl chloride is calculated (Eq. 1). 13 13 13 δ Cpropionyl chloride = ((δ Cfentanyl + 1) – (δ C4-ANPP * 0.8636))/0.1364 Eq. 1 The linkage process involves the use of data from multiple methodologies, however, isotopic profiles of the illicit fentanyl, 4-ANPP, and propionyl chloride are essential. While carbon and nitrogen isotope data are critical, measuring the isotopic contributions from 2H and 18O could prove to add even more discriminatory power. Currently, the DEA routinely measures δ2H and δ18O in cocaine and methamphetamine with a traditional column set-up. Fentanyl presents some difficulties with this method due to its higher nitrogen content, and a new instrumental method is required that utilizes chromium. A new method was developed and investigated for future implementation into FSPP. The data collected and outlook of this method are presented within. Materials and Methods Materials All chemicals and solvents used were reagent grade or better and were obtained from Sigma- Aldrich. Illicit Fentanyl Nine kg of illicit fentanyl were seized in Baltimore, MD. Seven samples were removed from each of the nine kilograms (Figure 2) to result in 63 representative samples. Additionally, more than 340 illicit fentanyl exhibits previously analyzed by the FSPP were submitted for further isotope analyses. Illicit Fentanyl Isotope Investigation 5 This resource was prepared by the author(s) using Federal funds provided by the U.S. Department of Justice. Opinions or points of view expressed are those of the author(s) and do not necessarily reflect the official position or policies of the U.S. Department of Justice. Figure 2. Photograph of one sampled kilogram to illustrate sampling pattern. Each of the nine kilograms were sampled in the same manner. Gas Chromatography/Flame Ionization Detection (GC/FID) Fentanyl quantitation was performed using an Agilent (Palo Alto, CA) Model 7890A gas chromatograph with flame ionization detection. The GC system was fitted with a 30 m x 0.25 mm ID fused-silica capillary column coated with DB-1 (0.25 µm) (Agilent, Santa Clara, CA) in constant flow mode at 43.5 cm/s of hydrogen carrier gas. The injection port and flame ionization detectors were maintained at 280oC.
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