Acetylfentanyl

Acetylfentanyl
Systematic (IUPAC) name
N-(1-Phenethylpiperidin-4-yl)-N-phenylacetamide
Clinical data
Routes of
administration		 oral, iv, im, insuflation
Legal status
Legal status
Identifiers
CAS Number 3258-84-2
ATC code none
PubChem CID 527015
ChemSpider 459388
Synonyms Acetyl fentanyl
Chemical data
Formula C21H26N2O
Molar mass 322.44 g/mol

Acetylfentanyl (acetyl fentanyl) is an opioid analgesic drug that is an analog of fentanyl. Studies have estimated acetylfentanyl is between five to fifteen times more potent than heroin.[3] Additionally it is reported as being 80 times more potent than morphine, and 15 times less potent than fentanyl.[4] It has never been licensed for medical use and has only been sold illegally as a designer drug. Acetylfentanyl was discovered at the same time as fentanyl itself and had rarely been encountered on the illicit market in the late 1980s, but was never commonly used. However, in 2013, Canadian police discovered a group distributing over 3 kilograms and 12,400 pills of Acetylfentanyl equal to 117,400 doses.[5] As a μ-opioid receptor agonist, acetylfentanyl may serve as a direct substitute for heroin or other μ-opioid receptor agonist substances in opioid dependent individuals. 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.[6][7][8][9]

Deaths

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. This request led to 50 confirmed fatalities and five non-fatal overdoses statewide in 2013.[10][11] Another 5 deaths were reported in Jefferson Parish, New Orleans,[12] along with three more in North Carolina.[13]

Legal status

Canada

It is a Schedule 1 drug.[1] As it is an analog of fentanyl[14] and all fentanyl analogs are Schedule 1.

China

As of October, 2015 acetylfentanyl is a controlled substance in China.[15]

United States

Acetylfentanyl is a Schedule I controlled substance as of May 2015.[16]

The illegality of the drug has been supported by the charges against individuals for distribution of acetylfentanyl and possession with the intent to distribute acetylfentanyl.[2] The individual was sentenced to 3 years in prison by a federal court.[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.[3]

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. Retrieved 10 November 2013.
  2. 1 2 Neronha, Peter F. "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. Retrieved 10 November 2013.
  3. 1 2 Higashikawa, Yoshiyasu (2008-06-01). "Studies on 1-(2-phenethyl)-4-(N-propionylanilino) piperidine (fentanyl) and its related compounds: 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 1860-8973. Retrieved 27 August 2014.
  4. ↑ P. A. J. Janssen and C. A. M. van der Eycken in Drugs Affecting the Central Nervous System, Vol. 2, A. Burger, Ed., Marcel Dekker, New York, 1968, pp. 51-54.
  5. ↑ http://www.montrealgazette.com/mobile/story.html?id=8376600
  6. ↑ Jane Mounteney, Isabelle Giraudon, Gleb Denissov, Paul Griffiths (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe.". The international journal of drug policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
  7. ↑ Ruangyuttikarn, W; Law, MY; Rollins, DE; Moody, DE (1990). "Detection of fentanyl and its analogs by enzyme-linked immunosorbent assay". Journal of analytical toxicology 14 (3): 160–4. doi:10.1093/jat/14.3.160. PMID 2374405.
  8. ↑ CDC Issues Alert On Deadly New Designer Drug, Acetyl Fentanyl. David Kroll, Forbes Magazine, 29 August 2013
  9. ↑ Centers for Disease Control and Prevention (CDC) (2013). "Acetyl fentanyl overdose fatalities--Rhode Island, March-May 2013". MMWR. Morbidity and mortality weekly report 62 (34): 703–4. PMID 23985500.
  10. ↑ Ogilvie, Laurie, Christina Stanley, Lauren Lewis, Molly Boyd, Matthew Lozier, Matthew Lozier. "Notes from the Field: Acetyl Fentanyl Overdose Fatalities — Rhode Island, March–May 2013". cdc.gov. Center for Disease Control and Prevention. Retrieved 11 November 2013.
  11. ↑ Pennsylvania Department of Drug and Alcohol Programs. "Department of Drug and Alcohol Programs warns about acetyl fentanyl: drug caused at least 50 fatalities in 2013 in Pennsylvania.". Pennsylvania Department of Drug and Alcohol Programs.
  12. ↑ Grunfeld, David (November 1, 2013). "Couple found dead in Old Metairie home killed by lethal new synthetic drug". NOLA.com | The Times-Picayune. Retrieved 28 March 2014.
  13. ↑ "DHHS Issues Health Advisory for Deadly New Synthetic Drug". NC DHHS Press Releases. North Carolina Department of Health and Human Services. Retrieved 27 August 2014.
  14. ↑ "Definitions and interpretations". IsomerDesign. Retrieved 10 November 2013.
  15. ↑ "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 Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
  16. ↑ "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.
  17. ↑ "Seller of synthetic opiate gets 3 years in prison". Associated Press. 29 November 2013. Retrieved 28 March 2014.
  18. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
  19. ↑ "The Misuse of Drugs Act 1971 (Modification) Order 1986". UK Home Office. 1986. Retrieved 2 February 2016. Context: http://www.legislation.gov.uk/ukpga/1971/38/schedule/2 .
  20. ↑ Patton, A.L.; Seely, K.A.; Pulla, S. (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.
  21. ↑ Baselt RC (2014). Disposition of toxic drugs and chemicals in man. Seal Beach, Ca.: Biomedical Publications. ISBN 978-0-9626523-9-4.http://www.biomedicalpublications.com/acetylfentanyl.pdf

Further reading

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