Acryloylfentanyl, a recently emerged new psychoactive substance: a comprehensive review (original) (raw)
Gulland JM, Robinson R (1925) The constitution of codeine and thebaine. Mem Proc Manchester Lit Phil Soc 69:79–86 CAS Google Scholar
Casy AF, Parfitt RT (1986) Opioid analgesics: chemistry and receptors. Plenum Press, New York Book Google Scholar
Janssen PAJ (1965) 1-Aralkyl-4-(_N_-aryl-carbonyl amino)piperidines and related compounds. US Patent 3,164,600, assigned to Research Laboratorium Dr. C. Janssen N.V.
Janssen PAJ, Van der Eycken CAM (1968) The chemical anatomy of potent morphine-like analgesics. In: Burger A (ed) Drugs affecting the central nervous system. Marcel Dekker, NewYork, pp 25–60 Google Scholar
Van Bever WFM, Niemegeers CJE, Schellekens KHL, Janssen PAJ (1976) _N_-4-Substituted 1-(2-arylethyl)-4-piperidinyl-_N_-phenylpropanamides, a novel series of extremely potent analgesics with unusually high safety margin. Arzneimittelforschung 26:1548–1551 PubMed Google Scholar
Van Daele PGH, De Bruyn MFL, Boey JM, Sanczuk S, Agten JTM, Janssen PAJ (1976) Synthetic analgesics: _N_-(1-[2-arylethyl]-4-substituted 4-piperidinyl) _N_-arylalkanamides. Arzneimittelforschung 26:1521–1531 PubMed Google Scholar
KuKanich B, Papich MG (2009) Opioid analgesic drugs. In: Riviere JE, Papich HR (eds) Veterinary pharmacology and therapeutics. Wiley-Blackwell, Ames, pp 301–335 Google Scholar
Lance RW, Kenny DE (2012) Thiafentanil oxalate (A3080) in nondomestic ungulate species. In: Muller RE, Fowler M (eds) Fowler’s zoo and wild animal medicine: current therapy. Saunders, St. Louis, pp 589–595 Chapter Google Scholar
Romberg R, Sarton E, Teppema L, Matthes HWD, Kieffer BL, Dahan A (2003) Comparison of morphine-6-glucuronide and morphine on respiratory depressant and antinociceptive responses in wild type and μ-opioid receptor deficient mice. Br J Anaesth 91:862–870. doi:10.1093/bja/aeg279 ArticleCASPubMed Google Scholar
Anonymous (1983) New fentanyl compound. Microgram 16:147 Google Scholar
Henderson GL (1988) Designer drugs: past history and future prospects. J Forensic Sci 33:569–575 ArticleCASPubMed Google Scholar
Henderson GL (1991) Fentanyl-related deaths: demographics, circumstances, and toxicology of 112 cases. J Forensic Sci 36:422–433 ArticleCASPubMed Google Scholar
U.S. Drug Enforcement Administration (2007) Control of a chemical precursor used in the illicit manufacture of fentanyl as a List I chemical. Fed Regist 72:20039–20047 Google Scholar
Schumann H, Erickson T, Thompson TM, Zautcke JL, Denton JS (2008) Fentanyl epidemic in Chicago, Illinois and surrounding Cook County. Clin Toxicol 46:501–506. doi:10.1080/15563650701877374 ArticleCAS Google Scholar
U.S. Drug Enforcement Administration (2017) Control of immediate precursor used in the illicit manufacture of fentanyl as a schedule II controlled substance. Fed Regist 75:37295–37299 Google Scholar
Tuusov J, Vals K, Tõnisson M, Riikoja A, Denissov G, Väli M (2013) Fatal poisoning in Estonia 2000–2009. Trends in illegal drug-related deaths. J Forensic Legal Med 20:51–56. doi:10.1016/j.jflm.2012.04.023 ArticleCAS Google Scholar
Mounteney J, Giraudon I, Denissov G, Griffiths P (2015) Fentanyls: are we missing the signs? Highly potent and on the rise in Europe. Int J Drug Policy 26:626–631. doi:10.1016/j.drugpo.2015.04.003 ArticlePubMed Google Scholar
Centers for Disease Control and Prevention (2015) Increases in fentanyl drug confiscations and fentanyl-related overdose fatalities. CDCHAN-00384. CDC Health Alert Advisory, October 26, 2015. https://emergency.cdc.gov/han/han00384.asp. Accessed 22 April 2017
Sutter ME, Gerona RR, Davis MT, Roche BM, Colby DK, Chenoweth JA, Adams AJ, Owen KP, Ford JB, Black HB, Albertson TE (2017) Fatal fentanyl: one pill can kill. Acad Emerg Med 24:106–113. doi:10.1111/acem.13034 ArticlePubMed Google Scholar
San Francisco Department of Public Health (2015) Severe opioid overdoses in San Francisco caused by fentanyl-containing “Xanax” pill. 10-22-2015. http://www.sfcdcp.org/document.html?id=1005. Accessed 22 April 2017
Klar SA, Brodkin E, Gibson E, Padhi S, Predy C, Green C, Lee V (2016) Notes from the field: furanyl-fentanyl overdose events caused by smoking contaminated crack cocaine—British Columbia, Canada, July 15–18, 2016. MMWR Morb Mortal Wkly Rep 65:1015–1016. http://dx.doi.org/10.15585/mmwr.mm6537a6. Accessed 22 April 2017
Tomassoni AJ, Hawk KF, Jubanyik K, Nogee DP, Durant T, Lynch KL, Patel R, Dinh D, Ulrich A, D’Onofrio G (2017) Multiple fentanyl overdoses—New Haven, Connecticut, June 23, 2016. MMWR Morb Mortal Wkly Rep 66:107–111. http://dx.doi.org/10.15585/mm6604a4. Accessed 22 April 2017
European Monitoring Centre for Drugs and Drug Addiction (2016) EMCDDA–Europol Joint Report on a new psychoactive substance: _N_-phenyl-_N_-[1-(2-phenylethyl)piperidin-4-yl] acetamide (acetylfentanyl). Publications Office of the European Union, Luxembourg. http://www.emcdda.europa.eu/system/files/publications/2693/TDAS16001ENN.PDF. Accessed 22 April 2017. doi: 10.2810/890694
Evans-Brown M, Sedefov R (2017) New psychoactive substances: driving greater complexity into the drug problem. Addiction 112:36–38. doi:10.1111/add.13528 ArticlePubMed Google Scholar
Zhu Y, Ge B, Fang S, Zhu Y, Dai Q, Tan Z, Huang Z, Ghen X (1981) Studies on potent analgesics. I. Synthesis and analgesic activity of derivatives of fentanyl (in Chinese). Yaoxue Xuebao [Acta Pharmaceutica Sinica] 16:199–210 CAS Google Scholar
Maryanoff BE, Simon EJ, Gioannini T, Gorissen H (1982) Potential affinity labels for the opiate receptor based on fentanyl and related compounds. J Med Chem 25:903–909. doi:10.1021/jm00350a006 Article Google Scholar
Clark AB, Nelson JD (1984) China White—a California phenomenon. Abstract. J Forensic Sci Soc 24:284 Google Scholar
Cooper D, Jacob M, Allen A (1986) Identification of fentanyl derivatives. J Forensic Sci 31:511–528 ArticleCASPubMed Google Scholar
Valter K, Arrizabalaga P (1998) Designer drugs directory. Elsevier Science SA, Amsterdam, p 166 Book Google Scholar
Essawi MYH (1998) Synthesis of fentanyl analogues as nonequilibrium irreversible ligands for opioid receptors. Bull Fac Pharmacy (Cairo Univ) 36(3):39–45 CAS Google Scholar
Essawi MYH (1999) Fentanyl analogues with a modified propanamido group as potential affinity labels: synthesis and in vivo activity. Pharmazie 54:307–308 CASPubMed Google Scholar
Prodduturi S, Smith GJ, Wokowich AM, Doub WH, Westenberger BJ, Buhse L (2009) Reservoir based fentanyl transdermal drug delivery systems: effect of patch age on drug release and skin permeation. Pharm Res 26:1344–1352. doi:10.1007/s11095-009-9843-0 ArticleCASPubMed Google Scholar
Moffat AC, Osselton MD, Widdop B (2011) Clarke’s analysis of drugs and poisons. Pharmaceutical Press, London, pp 1400–1402 Google Scholar
Hansch C, Leo A, Hoekman D (1995) Exploring QSAR. Hydrophobic, electronic, and steric constants. American Chemical Society, Washington, DC, p 348 Google Scholar
Vardanyan RS, Hruby VJ (2015) Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications. Future Med Chem 6:385–412. doi:10.4155/fmc.13.215 Article Google Scholar
Breindhal T, Kimergård A, Andreasen MF, Pedersen DS (2016) Identification of a new psychoactive substance in seized material: the synthetic opioid _N_-phenyl-_N_-[1-(2-phenethyl)piperidin-4-yl]propen-2-amide (Acrylfentanyl). Drug Test Anal 9:415–422. doi:10.1002/dta.2046 Article Google Scholar
Huckle D, Lockhart IM, Wright M (1972) 4,5-Dihydro-1-benzoxepin-3(2_H_)-one, N_-substituted 2,3-dihydro-1,5-benzoxazepin-4(5_H)-ones, and related compounds. J Chem Soc Perkin Trans 1 1972:2425–2428. doi:10.1039/P19720002425 Article Google Scholar
Rittgen J, Pütz M, Zimmerman R (2012) Identification of fentanyl derivatives at trace levels with nonaqueous capillary electrophoresis-electrospray-tandem mass spectrometry (MS_n_, n = 2, 3): analytical method and forensic applications. Electrophoresis 33:1595–1605. doi:10.1002/elps.201100655 ArticleCASPubMed Google Scholar
Helander A, Bäckberg M, Signell P, Beck O (2017) Intoxications involving acrylfentanyl and other novel designer fentanyls—results from the Swedish STRIDA project. Clin Toxicol. doi:10.1080/15563650.2017.1303141 Google Scholar
Watanabe S, Vikingsson S, Roman M, Green H, Kronstrand R, Wohlfarth A (2017) In vitro and in vivo metabolite identification for the new synthetic opioids acetylfentanyl, acrylfentanyl, furanylfentanyl, and 4-fluoroisobutyrylfentanyl. AAPS J. doi:10.1208/s12248-017-0070-z Google Scholar
Gupta PK, Yadav SK, Bhutia YD, Singh P, Rao P, Gujar NL, Ganesan K, Bhattacharya R (2013) Synthesis and comparative bioefficacy of _N_-(1-phenethyl-4-piperidinyl)propionanilide (fentanyl) and its 1-substituted analogs in Swiss albino mice. Med Chem Res 22:3888–3896. doi:10.1007/s00044-012-0390-6 ArticleCAS Google Scholar
Vuckovic S, Prostran M, Ivanovic M, Dosen-Micovic L, Savic Vujovic K, Vucetic C, Kadija M, Mikovic Z (2011) Pharmacological evaluation of 3-carbomethoxy fentanyl in mice. Pharmaceuticals 4:233–243. doi:10.3390/ph4020233 ArticleCASPubMed Central Google Scholar
Vartanyan RS, Martirosyan VO, Vartanyan SA, Vlasenko ÉV, Durgaryan LK, Azlivyan AS (1989) Synthesis and analgesic activity of 4-anilides of 1-substituted-2,5-dimethylpiperidines. Pharm Chem J 23:383–387. doi:10.1007/BF00758289 Article Google Scholar
Archer S, Michael J, Michael M, Simon EJ, Abdelhamid EME, Nelson WL, Koolpe GA (1985) Chloroacryloyl amides and alpha-methylenelactones from naltrexone, oxymorphone and fentanyl. Neuropeptides 5:395–398 ArticleCASPubMed Google Scholar
Jöst C, Nitsche C, Scholz T, Roux L, Klein CD (2014) Promiscuity and selectivity in covalent enzyme inhibition: a systematic study of electrophilic fragments. J Med Chem 57:7590–7599. doi:10.1021/jm5006918 ArticlePubMed Google Scholar
Goromaru T, Matsuura H, Yoshimura N, Miyawaki T, Sameshima T, Miyao J, Furuta T, Baba S (1984) Identification and quantitative determination of fentanyl metabolites in patients by gas chromatography–mass spectrometry. Anesthesiology 61:73–77 ArticleCASPubMed Google Scholar
Guitton J, Désage M, Alamercery S, Dutruch L, Dautraix S, Perdrix JP, Brazier JL (1997) Gas chromatographic–mass spectrometry and gas chromatographic–Fourier transform infrared spectroscopy assay for the simultaneous identification of fentanyl metabolites. J Chromatogr B 59:59–70. doi:10.1016/S0378-4347(97)00050-9 Article Google Scholar
DePriest AZ, Puet BL, Holt AC, Roberts A, Cone EJ (2015) Metabolism and disposition of prescription opioids: a review. Forensic Sci Rev 27:115–145 CASPubMed Google Scholar
Patton AL, Seely KA, Pulla S, Rusch NJ, Moran CL, Fantegrossi WE, Knight LD, Marraffa JM, Kennedy PD, James LP, Endres GW, Moran JH (2014) Quantitative measurement of acetyl fentanyl and acetyl norfentanyl in human urine by LC-MS/MS. Anal Chem 86:1760–1766. doi:10.1021/ac4036197 ArticleCASPubMed Google Scholar
Melen’tev AB, Kataev SS, Dvorskaya ON (2015) Identification and analytical properties of acetyl fentanyl metabolites. J Anal Chem 70:240–248. doi:10.1134/S1061934815020124 Article Google Scholar
Poklis J, Poklis A, Wolf C, Mainland M, Hair L, Devers K, Chrostowski L, Arbefeville E, Merves M, Pearson J (2015) Postmortem tissue distribution of acetyl fentanyl, fentanyl and their respective nor-metabolites analyzed by ultrahigh performance liquid chromatography with tandem mass spectrometry. Forensic Sci Int 257:435–441. doi:10.1016/j.forsciint.2015.10.021 ArticleCASPubMedPubMed Central Google Scholar
Labroo RB, Paine MF, Thummel KE, Kharasch ED (1997) Fentanyl metabolism by human hepatic and intestinal cytochrome P450 3A4: implications for interindividual variability in disposition, efficacy, and drug interactions. Drug Metab Dispos 25:1072–1080 CASPubMed Google Scholar
Higashikawa Y, Suzuki S (2008) Studies on 1-(2-phenethyl)-4-(_N_-propionylanilino)piperidine (fentanyl) and its related compounds: novel metabolites in rat urine following injection of α-methylfentanyl, one of the most abused typical designer drug. J Health Sci 54:629–637. doi:10.1248/jhs.54.629 ArticleCAS Google Scholar
Jin M, Gock SB, Jannetto PJ, Jentzen JM, Wong SH (2005) Pharmacogenomics as molecular autopsy for forensic toxicology: genotyping cytochrome P450 3A4*1B and 3A5*3 for 25 fentanyl cases. J Anal Toxicol 29:590–598. doi:10.1093/jat/29.7.590 ArticleCASPubMed Google Scholar
European Monitoring Centre for Drugs and Drug Addiction (2015) Preventing fatal overdoses: a systematic review of the effectiveness of take-home naloxone, EMCDDA Papers. Publications Office of the European Union, Luxembourg. doi:10.2810/396726
Centers for Disease Control and Prevention (2013) Recommendations for laboratory testing for acetyl fentanyl and patient evaluation and treatment for overdose with synthetic opioid. CDC Health Alert Advisory, June 20, 2013. http://emergency.cdc.gov/han/han00350.asp. Accessed 22 April 2017
Martin M, Hecker J, Clark R, Frye J, Jehle D, Lucid EJ, Harchelroad F (1991) China White epidemic: an eastern United States emergency department experience. Ann Emerg Med 20:158–164. doi:10.1016/S0196-0644(05)81216-8 ArticleCASPubMed Google Scholar
Bäckberg M, Beck O, Jönsson K-H, Helander A (2015) Opioid intoxications involving butyrfentanyl, 4-fluorobutyrfentanyl, and fentanyl from the Swedish STRIDA project. Clin Toxicol 53:609–617. doi:10.3109/15563650.2015.1054505 Article Google Scholar