Acetylfentanyl

Acetylfentanyl
Clinical data
Routes of
administration		 oral, iv, im, insuflation
ATC code none
Legal status
Legal status
Identifiers
Synonyms Acetyl fentanyl
CAS Number 3258-84-2
PubChem (CID) 527015
ChemSpider 459388
UNII 6DZ28538KS
Chemical and physical data
Formula C21H26N2O
Molar mass 322.44 g/mol
3D model (Jmol) Interactive image

Acetylfentanyl (acetyl fentanyl) is an opioid analgesic drug that is an analog of fentanyl.[4] Studies have estimated acetylfentanyl to be fifteen times more potent than morphine.[5][6] It has never been licensed for medical use and instead only been sold as a designer drug. Acetylfentanyl was discovered at the same time as fentanyl itself and had only rarely been encountered on the illicit market in the late 1980s. However, in 2013, Canadian police seized 3 kilograms of acetylfentanyl.[7] As a μ-opioid receptor agonist, acetylfentanyl may serve as a direct substitute for heroin or other opioids. Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.[8][9][10]

Deaths

Europe

Acetylfentanyl has been analytically confirmed in 32 fatalities in four European member states between 2013 and August 2015, Germany (2), Poland (1), Sweden (27) and the United Kingdom (2).[3]

Russia

Twelve deaths have been associated with acetylfentanyl in Russia since 2012.[3][11]

USA

The Centers for Disease Control and Prevention (CDC) issued a health alert to report that between March 2013 and May 2013, 14 overdose deaths related to injected acetylfentanyl had occurred among intravenous drug users (ages between 19 and 57 years) in Rhode Island. After confirming five overdoses in one county, including a fatality, Pennsylvania asked coroners and medical examiners across the state to screen for acetylfentanyl. As a result of this investigation, Pennsylvania confirmed at least one acetylfentanyl overdose death and attributed at least 50 fatalities to either fentanyl or acetylfentanyl during the first half of 2013.[12][13] In July 2015, the DEA informed about 52 confirmed fatalities involving acetylfentanyl in the United States between 2013 and 2015.[14]

Japan

One fatal poisoning caused by intravenous injection of a "bath salt" product containing acetylfentanyl and 4'-Methoxy-α-pyrrolidinoheptiophenone has been reported in 2016.[15]

Legal status

Canada

As an analog of fentanyl, acetylfentanyl is a Schedule I controlled drug.[1]

China

As of October, 2015 acetylfentanyl is a controlled substance in China.[16]

United States

Acetylfentanyl is a Schedule I controlled substance as of May 2015.[17]

Switzerland

Acetylfentanyl is illegal in Switzerland as of December 2015.[18]

United Kingdom

Acetylfentanyl was made a class A drug as an analogue of fentanyl in 1986.[19]

Overdose

Acetylfentanyl overdosage has been reported to closely resemble heroin overdosage clinically. Additionally, while naloxone (Narcan) is effective in treating acetylfentanyl overdose, larger than normal doses of the antidote may be required.[5]

Detection in body fluids

Acetylfentanyl may be quantitated in blood, plasma or urine by liquid chromatography-mass spectrometry to confirm a diagnosis of poisoning in hospitalized patients or to provide evidence in a medicolegal death investigation. Postmortem peripheral blood acetylfentanyl concentrations have been in a range of 89–945 μg/L in victims of acute overdosage.[20][21]

See also

References

  1. 1 2 "Controlled Drugs and Substances Act". IsomerDesign.
  2. ↑ "Two Charged With Witness Tampering in Joint Woonsocket Police, DEA Investigation". The United States Attorney's Office: District of Rhode Island. US Department of Justice. 6 June 2013.
  3. 1 2 3 "EMCDDA–Europol Joint Report on acetylfentanyl". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). June 2016. doi:10.2810/890694.
  4. ↑ Helander, Anders; Bäckberg, Matilda; Beck, Olof (20 April 2016). "Intoxications involving the fentanyl analogs acetylfentanyl, 4-methoxybutyrfentanyl and furanylfentanyl: results from the Swedish STRIDA project". Clinical Toxicology. 54 (4): 324–332. doi:10.3109/15563650.2016.1139715. ISSN 1556-3650. PMID 26850293.
  5. 1 2 Higashikawa, Yoshiyasu; Suzuki, Shinichi (June 2008). "Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure-analgesic activity relationship for fentanyl, methyl-substituted fentanyls and other analogues". Forensic Toxicology. 26 (1): 1–5. doi:10.1007/s11419-007-0039-1. ISSN 1860-8965.
  6. ↑ Aceto, M. D.; Bowman, E. R.; Harris, L. S.; May, E. L. (1989). "Dependence studies on new compounds in the rhesus monkey, rat and mouse" (PDF). NIDA research monograph. 95: 578–631. ISSN 1046-9516. PMID 2641054.
  7. ↑ "Extremely potent painkiller hits Montreal black market". CBS News. 13 May 2013.
  8. ↑ Mounteney, Jane; Giraudon, Isabelle; Denissov, Gleb; Griffiths, Paul (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
  9. ↑ Ruangyuttikarn, Werawan; Law, Michael Y.; Rollins, Douglas E.; Moody, David E. (May–June 1990). "Detection of Fentanyl and its Analogs by Enzyme-Linked Immunosorbent Assay". Journal of Analytical Toxicology. 14 (3): 160–164. doi:10.1093/jat/14.3.160. ISSN 0146-4760. PMID 2374405.
  10. ↑ Kroll, David (29 August 2013). "CDC Issues Alert On Deadly New Designer Drug, Acetyl Fentanyl".
  11. ↑ Melent’ev, A.B.; Kataev, S.S.; Dvorskaya, O.N. (February 2015). "Identification and analytical properties of acetyl fentanyl metabolites". Journal of Analytical Chemistry. 70 (2): 240–248. doi:10.1134/S1061934815020124. ISSN 1061-9348.
  12. ↑ Centers for Disease Control and Prevention (CDC) (30 August 2013). "Acetyl fentanyl overdose fatalities--Rhode Island, March-May 2013". MMWR. Morbidity and mortality weekly report. 62 (34): 703–704. ISSN 1545-861X. PMID 23985500.
  13. ↑ Lozier, MatthewJ.; Boyd, Molly; Stanley, Christina; Ogilvie, Laurie; King, Ewa; Martin, Colleen; Lewis, Lauren (June 2015). "Acetyl Fentanyl, a Novel Fentanyl Analog, Causes 14 Overdose Deaths in Rhode Island, March–May 2013". Journal of Medical Toxicology. 11 (2): 208–217. doi:10.1007/s13181-015-0477-9. ISSN 1556-9039. PMC 4469714Freely accessible. PMID 25934111.
  14. ↑ Drug Enforcement Administration (July 2015). "Acetyl fentanyl" (PDF). Drug Enforcement Administration Office of Diversion Control.
  15. ↑ Yonemitsu, Kosei; Sasao, Ako; Mishima, Satoko; Ohtsu, Yuki; Nishitani, Yoko (2016). "A fatal poisoning case by intravenous injection of "bath salts" containing acetyl fentanyl and 4-methoxy PV8". Forensic Science International. doi:10.1016/j.forsciint.2016.08.025.
  16. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in cn). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
  17. ↑ "80 FR 29227 - Schedules of Controlled Substances: Temporary Placement of Acetyl Fentanyl into Schedule I". U.S. Government Publishing Office (GPO). 21 May 2015. Retrieved 30 June 2015.
  18. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat. 1 December 2015.
  19. ↑ "The Misuse of Drugs Act 1971 (Modification) Order 1986". UK Home Office. 16 December 1986.
  20. ↑ Patton, Amy L.; Seely, Kathryn A.; Pulla, Sharon; Rusch, Nancy J.; Moran, Cindy L.; Fantegrossi, William E.; Knight, Laura D.; Marraffa, Jeanna M.; Kennedy, Paul D.; James, Laura P.; Endres, Gregory W.; Moran, Jeffery H. (February 2014). "Quantitative Measurement of Acetyl Fentanyl and Acetyl Norfentanyl in Human Urine by LC-MS/MS". Analytical Chemistry. 86 (3): 1760–1766. doi:10.1021/ac4036197. PMID 24354295.
  21. ↑ Randall C. Baselt (2014). "Acetylfentanyl". Disposition of toxic drugs and chemicals in man (PDF). Seal Beach, Ca.: Biomedical Publications. ISBN 978-0-9626523-9-4.

Further reading

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