Decontamination of Fentanyl and Fentanyl Analogues in Field and Laboratory Settings: A Review of Fentanyl Degradation
Mikaela M. Bazley A , Michael Logan B , Christina Baxter C , Avril A. B. Robertson
A and Joanne T. Blanchfield A D
A School of Chemistry and Molecular Biosciences, University of Queensland, St Lucia, Qld 4072, Australia.
B Research and Scientific Branch, Queensland Fire and Emergency Services, Cannon Hill, Qld 4170, Australia.
C Emergency Response TIPS, LLC, Melbourne Beach, Florida, USA.
D Corresponding author. Email: j.blanchfield@uq.edu.au
After Ms Mikaela Bazley completed her undergraduate degree (B.Sc.) and Honours in chemistry at The University of Queensland in 2015, she was employed by the Queensland Fire and Emergency Services Research and Scientific Branch as a graduate chemist working on the Emergency Response Decision Support Software (ERDSS) developed in conjunction with United States government agencies. Mikaela commenced her Ph.D. at the University of Queensland in 2018. |
Dr Michael Logan leads the Research and Scientific Branch within the Queensland Fire and Emergency Services. He has a Ph.D. in physical chemistry from the University of New South Wales and has been awarded the Australian Fire Service Medal. He has responded to more than 1800 HAZMAT incidents across Queensland, Australia, and internationally. These have ranged from illicit laboratories, biological-related releases, radiological incidents, and chemical fires, spills, and explosions. |
Dr Christina Baxter is the CEO of Emergency Response TIPS, LLC, which provides practical, evidence-based solutions for emergency response through education, product design, and technology transition. Prior to forming Emergency Response TIPS, LLC, Dr Baxter was the CBRNE Program Manager for the Department of Defense’s Combating Terrorism Technical Support Office. She holds a Ph.D. in analytical chemistry from the Georgia Institute of Technology and Bachelor of Science degrees in environmental science and chemistry from the University of Massachusetts at Amherst. |
Avril A. B. Robertson is Professor and Director of Biotechnology Programs at The University of Queensland. Professor Robertson completed her Ph.D. in 2000 in bioorganic chemistry at the University of St Andrews. She spent 10 years in the UK biotechnology and drug discovery industry before moving to The University of Queensland as Head of Medicinal Chemistry in the Center for Drug Design and Discovery in 2011. In 2017, she progressed to full Professor and Director of Biotechnology and also sits on the Board of Directors of the National Professional Science Masters Association in the USA. |
Professor Joanne Blanchfield completed a B.Sc. with Honours and a Ph.D. in organic chemistry at The University of Queensland. She then embarked on a research career at Johns Hopkins University, Baltimore, and the Australian National University, Canberra, before returning to The University of Queensland to take up an academic career. She leads a research group with interests in drug delivery, design, and development and natural products isolation and characterisation. She also teaches widely across all levels of tertiary education and is Chair of Teaching and Learning for the School of Chemistry and Molecular Biosciences. |
Australian Journal of Chemistry 73(10) 868-879 https://doi.org/10.1071/CH19669
Submitted: 31 December 2019 Accepted: 24 February 2020 Published: 19 June 2020
Abstract
On account of their efficacy as µ-opioid receptor agonists, fentanyl and fentanyl analogues (‘fentanyls’) have fallen into favour within the illicit drug community. Consequently, there has been a significant public health crisis, unfolding across many countries, involving fentanyls and other synthetic opioids. Because of the potency of these opioids, even low-level contamination represents an immediate threat to the life and health of unprotected personnel and poses significant challenges to decontamination of sites where they are present. A dimension that exacerbates these challenges is the spillage of fentanyls in non-traditional settings such as residence, and clandestine manufacturing facilities. Hence, the decontamination of these sites and neutralisation of fentanyls where they are discovered is a key requirement in site remediation. There is currently much uncertainty around the limited operational procedures promoted for the decontamination of fentanyls in operational settings due to significant gaps in knowledge about fentanyl degradation. This review provides a comprehensive survey of the literature pertaining to the forced degradation of fentanyl and its analogues. By assessing the current state of the art regarding fentanyl degradation, including identifying knowledge gaps, the authors provide recommendations for future studies. These recommendations aim to address these gaps so that future guidance provided to first responders is based on sound scientific evidence about the chemical degradation of fentanyl and its analogues.
References
[1] D. J. Trump, Presidential Memorandum for the Heads of Executive Departments and Agencies [Internet]. Washington D.C.: Presidential Memoranda; 2017 [updated 2017; cited 30 October 2019]. Available at: https://www.whitehouse.gov/presidential-actions/presidential-memorandum-heads-executive-departments-agencies/ (accessed 30 October 2019)[2] E. D. Hargan, Determination that a Public Health Emergency Exists [Internet]. Washington D.C.: Office of the Secretary; 2017 [updated 2017; cited 30 October 2019]. Available at: https://www.hhs.gov/sites/default/files/opioid%20PHE%20Declaration-no-sig.pdf (accessed 30 October 2019)
[3] P. Armenian, K. T. Vo, J. Barr-Walker, K. L. Lynch, Neuropharmacology 2018, 134, 121.
| Crossref | GoogleScholarGoogle Scholar | 29042317PubMed |
[4] Centres for Disease Control and Prevention, Increases in Fentanyl Drug Confiscations and Fentanyl-related Overdose Fatalities [Internet]. United States: U.S. Department of Health & Human Services; 2018 [updated 2015; cited 4 June 2018]. Available at: https://emergency.cdc.gov/han/han00384.asp (accessed 4 June 2018)
[5] A. B. Peterson, R. M. Gladden, C. Delcher, E. Spies, A. Garcia-Williams, Y. Wang, J. Halpin, J. Zibbell, C. L. McCarty, J. DeFiore-Hyrmer, B. M. DiOrio, B. A. Goldberger, Morb. Mortal. Wkly. Rep. 2016, 65, 844.
| Crossref | GoogleScholarGoogle Scholar |
[6] Drug Enforcement Agency, DEA Issues Nationwide Alert on Fentanyl as Threat to Health and Public Safety [Internet]. Washington, U.S.: National Media Affairs Office; 2015 [updated 18 March 2018]. Available at: https://www.dea.gov/divisions/hq/2015/hq031815.shtml (accessed 5 June 2018)
[7] H. Schumann, T. Erickson, T. M. Thompson, J. L. Zautcke, J. S. Denton, Clin. Toxicol. 2008, 46, 501.
| Crossref | GoogleScholarGoogle Scholar |
[8] Centres for Disease Control and Prevention, Reported Law Enforcement Encounters Testing Positive for Fentanyl Increase Across US [Internet]. United States.: U.S. Department of Health & Human Services; 2016 [updated 24 August 2016]. Available at: https://www.cdc.gov/drugoverdose/data/fentanyl-le-reports.html (accessed 5 June 2018)
[9] R. Gladden, P. Martinez, P. Seth, Morb. Mortal. Wkly. Rep. 2016, 65, 837.
| Crossref | GoogleScholarGoogle Scholar |
[10] H. E. McKeown, T. J. Rook, J. R. Pearson, O. A. H. Jones, Sci. Justice 2018, 58, 366.
| Crossref | GoogleScholarGoogle Scholar | 30193662PubMed |
[11] L. Belzak, J. Halverson, Health Promotion and Chronic Disease Prevention in Canada: Research, Policy and Practice 2018, 38, 224.
[12] B. Fischer, L. Vojtila, J. Rehm, Prev. Med. 2018, 107, 109.
| Crossref | GoogleScholarGoogle Scholar | 29126920PubMed |
[13] J. Mounteney, I. Giraudon, G. Denissov, P. Griffiths, Int. J. Drug Policy 2015, 26, 626.
| Crossref | GoogleScholarGoogle Scholar | 25976511PubMed |
[14] A. Roxburgh, L. Burns, O. H. Drummer, J. Pilgrim, M. Farrell, L. Degenhardt, Drug Alcohol Rev. 2013, 32, 269.
| Crossref | GoogleScholarGoogle Scholar | 23442164PubMed |
[15] J. Suzuki, S. El-Haddad, Drug Alcohol Depend. 2017, 171, 107.
| Crossref | GoogleScholarGoogle Scholar | 28068563PubMed |
[16] A. Poklis, J. Toxicol. Clin. Toxicol. 1995, 33, 439.
| Crossref | GoogleScholarGoogle Scholar | 7650768PubMed |
[17] J. F. Gualtieri, S. J. Roe, C. L. Schmidt, J. Toxicol. Clin. Toxicol. 2000, 38, 236.
[18] M. D. Reeves, C. J. Ginifer, Med. J. Aust. 2003, 178, 526.
| Crossref | GoogleScholarGoogle Scholar |
[19] P. W. Moore, R. B. Palmer, J. W. Donovan, J. Forensic Sci. 2015, 60, 243.
| Crossref | GoogleScholarGoogle Scholar | 25041753PubMed |
[20] G. Henderson, J. Forensic Sci. 1991, 36, 422.
| Crossref | GoogleScholarGoogle Scholar | 2066723PubMed |
[21] R. T. E. C. S. Registry, Propionanilide, N-(1-Phenethyl-4-piperidyl)- [Internet]. United States: Right Answer Knowledge Solutions OnLine; 2017 [updated 2017; cited 2 November 2017]. Available at: http://www.rightanswerknowledge.com/N1servefile_new.asp?SearchValueType=CN&searchTerm=fentanyl&searchPick=Fentanyl&searchPickCheck=&searchDB=RT&searchInterest=all&url=UE5550000 (accessed 2 November 2017)
[22] E. Durnal, P. Kelsey, Dahlgren Decontamination Studies Final Project Report R1. Chantilly, VA: June 2018. Report No.: 311493.
[23] D. Sutlovic, M. Definis-Gojanovic, Arch. Ind. Hyg. Toxicol. 2007, 58, 317.
| Crossref | GoogleScholarGoogle Scholar |
[24] C. Baxter, M. Logan, CBRNe World 2018, February, 25–28.
[25] D. Guerrieri, E. Rapp, M. Roman, G. Thelander, R. Kronstrand, Forensic Sci. Int. 2017, 277, e21.
| Crossref | GoogleScholarGoogle Scholar | 28587915PubMed |
[26] J. Graney, Alberta to Develop Guidelines to Clean Fentanyl Contaminated Sites [Internet]. Totonto, ON.: Edmonton Journal; 2018 [updated 24 August 2018; cited 20 September 2018]. Available at: https://edmontonjournal.com/news/local-news/alberta-to-develop-guidelines-to-clean-fentanyl-contaminated-sites (accessed 20 September 2018)
[27] J. Wong, New Provincial Guidelines in the Works to Clean Up Fentanyl-Contaminated Sites [Internet]. Canada: Global News; 2018 [updated 24 August 2018; cited 21 September 2018]. Available at: https://globalnews.ca/news/4407734/new-provincial-guidelines-in-the-works-to-clean-up-fentanyl-contaminated-sites/ (accessed 21 September 2018)
[28] M. Blevins, Fentanyl Lab Cleanup and the Growing Need for Educated Remediators [Internet]. Troy, MI: Restoration & Remediation Magazine; 2017 [updated 7 March 2017; cited 21 September 2018]. Available at: https://www.randrmagonline.com/articles/87303-fentanyl-lab-cleanup-the-growing-need-for-educated-remediators (accessed 21 September 2018)
[29] C. H. Arnaud, Detecting Traces of Fentanyl in the Field [Internet]. United States: Chemical and Engineering News; 2018 [updated 28 May 2018; cited 21 September 2018]. Available from: https://cen.acs.org/analytical-chemistry/forensic-science/Detecting-traces-fentanyl-field/96/i22 (accessed 21 September 2018)
[30] A. Garg, D. W. Solas, L. H. Takahashi, J. V. Cassella, J. Pharm. Biomed. Anal. 2010, 53, 325.
| Crossref | GoogleScholarGoogle Scholar | 20462721PubMed |
[31] L. Xu, L. Ren, Z. Wang, X. Tian, L. Qi, Q. Fan, Y. Xiang, Water Sci. Technol. 2015, 72, 38.
| Crossref | GoogleScholarGoogle Scholar | 26114269PubMed |
[32] L. Manral, P. Gupta, M. Suryanarayana, K. Ganesan, R. Malhotra, J. Therm. Anal. Calorim. 2009, 96, 531.
| Crossref | GoogleScholarGoogle Scholar |
[33] J. D. Rabinowitz, M. Wensley, P. Lloyd, D. Myers, W. Shen, A. Lu, C. Hodges, R. Hale, D. Mufson, A. Zaffaroni, J. Pharmacol. Exp. Ther. 2004, 309, 769.
| Crossref | GoogleScholarGoogle Scholar | 14752061PubMed |
[34] R. Nishikawa, Detection and Characterization of Pyromarkers of Smoked Drugs of Abuse 2012, Ph.D. thesis, West Virginia University, Morgantown, West Virginia, USA.
[35] Z. Czégény, M. Blazsó, J. Anal. Appl. Pyrolysis 2001, 58–59, 95.
| Crossref | GoogleScholarGoogle Scholar |
[36] L. Qi, Z. Cheng, G. Zuo, S. Li, Q. Fan, Def. Sci. J. 2011, 61, 30.
| Crossref | GoogleScholarGoogle Scholar |
[37] InterAgency Board, Recommendations on Selection and Use of Personal Protective Equipment and Decontamination Products for First Responders Against Exposure Hazards to Synthetic Opioids, Including Fentanyl and Fentanyl Analogues [Internet]. Arlington, VA: InterAgency Board: 2017 [updated August 2017; cited 8 April 2018]. Available from: https://www.health.nd.gov/media/1817/fr_ppedeconrec_fentanyl.pdf (accessed 8 April 2018)
[38] G. Reinhardt, G. Borchers, in Handbook of Detergents, Part E: Applications (Ed. U. Zoller) 2009, Vol. 141, pp. 387–402 (CRC Press: Boca Raton, FL).
[39] D. M. Davies, M. E. Deary, J. Chem. Soc., Perkin Trans. 2 1991, 1549.
| Crossref | GoogleScholarGoogle Scholar |
[40] Z. Yuan, Y. Ni, A. R. P. Van Heiningen, Can. J. Chem. Eng. 1997, 75, 42.
| Crossref | GoogleScholarGoogle Scholar |
[41] M. D. Tucker, D. E. Engler, inventors; Sandia Corporation, Albuquerque, NM (US), assignee. Decontamination Formulations for Disinfection and Sterilization. United States Patent US 7 271 137 B2 2007, 18 September.
[42] R. Curci, J. O. Edwards, in Catalytic Oxidations with Hydrogen Peroxide as Oxidant (Ed. S. Giorgio) 1992, pp. 45–95 (Springer: Dordrecht).
[43] J. O. Edwards, Peroxide Reaction Mechanisms 1962 (Interscience Publishers: New York, NY).
[44] G. L. K. Hoh, D. O. Barlow, A. F. Chadwick, D. B. Lake, S. R. Sheeran, J. Am. Oil Chem. Soc. 1963, 40, 268.
| Crossref | GoogleScholarGoogle Scholar |
[45] K. M. Ibne-Rasa, J. O. Edwards, J. Am. Chem. Soc. 1962, 84, 763.
| Crossref | GoogleScholarGoogle Scholar |
[46] First Line Technology LLC, Dahlgren Decon [Internet]. United States: MRI Global; 2018 [updated 2020; cited 15 April 2018]. Available at: http://www.cbrnetechindex.com/Print/4605/first-line-technology-llc/dahlgren-decon (accessed 15 April 2018)
[47] P. Kelsey, S. Humphrey, E. Durnal, Decon 7 Systems LLC, D7 Decontamination Studies Final Project Report. Scottsdale, Arizona: 2018 April. Report No.: 311525.01.001.
[48] S. Roy, G. Flynn, Pharm. Res. 1989, 6, 147.
| Crossref | GoogleScholarGoogle Scholar | 2569731PubMed |
[49] Organic Materials Review Institute, Technical Evaluation Report: Peracetic Acid. United States: 2016, March.
[50] S. Roy, G. Flynn, Pharm. Res. 1990, 7, 842.
| Crossref | GoogleScholarGoogle Scholar | 1978306PubMed |
[51] J. Lambropoulos, G. A. Spanos, N. V. Lazaridis, T. S. Ingallinera, V. K. Rodriguez, J. Pharm. Biomed. Anal. 1999, 20, 705.
| Crossref | GoogleScholarGoogle Scholar | 10704140PubMed |
[52] K. Takase, H. Masuda, O. Kai, Y. Nishiyama, S. Sakaguchi, Y. Ishii, Chem. Lett. 1995, 24, 871.
[53] H. Ohta, Y. Sakata, T. Takeuchi, Y. Ishii, Chem. Lett. 1990, 19, 733.
| Crossref | GoogleScholarGoogle Scholar |
[54] D. A. Kirby, Decomposition of Fentanyl: A Comparison Study. Presented at The 27th Annual CLIC Technical Training Seminar, 6–9 September 2017, Phoenix, AZ.
[55] N. M. Froelich, J. E. Sprague, T. J. Worst, J. Forensic Sci. 2018, 63, 336.
| Crossref | GoogleScholarGoogle Scholar | 29314013PubMed |
[56] CBRNe Portal, D7 Sets the Bar for Fentanyl Decon Test Standards [Internet]. Scottsdale, Arizona: CBRNe Portal; 2017 [updated 28 July 2017; cited January 2019]. Available at: https://www.cbrneportal.com/d7-sets-the-bar-for-fentanyl-decon-test-standards/ (accessed 25 January 2019)
