Benzoylfentanyl

Benzoylfentanyl
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class A; US: Schedule I; Illegal in Sweden and Finland;
Identifiers
	IUPAC name N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]benzamide;
CAS Number	2309383-15-9 ;
PubChem CID	139025450;
ChemSpider	77494315;
UNII	5MOH310W95;
CompTox Dashboard (EPA)	DTXSID401036812 ;
Chemical and physical data
Formula	C26H28N2O
Molar mass	384.523 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCC1N(C2=CC=CC=C2)C(=O)C3=CC=CC=C3)CCC4=CC=CC=C4;
	InChI InChI=1S/C26H28N2O/c29-26(23-12-6-2-7-13-23)28(24-14-8-3-9-15-24)25-17-20-27(21-18-25)19-16-22-10-4-1-5-11-22/h1-15,25H,16-21H2; Key:BJPDWVPQDSVQKD-UHFFFAOYSA-N;

Benzoylfentanyl, also known as phenylfentanyl, is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug.^[1]^[2] In the United States, benzoylfentanyl was first identified in Drug Enforcement Administration drug seizures in 2018.^[3]

Side effects

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.^[4] A new wave of fentanyl analogues and associated deaths began in around 2014 in the US, and have continued to grow in prevalence; especially since 2016 these drugs have been responsible for hundreds of overdose deaths every week.^[5]

Legal status

In the United States, fentanyl-related substances are Schedule I controlled substances.^[6] Benzoylfentanyl was banned in Finland in September 2017,^[7] and in Sweden in October 2017.^[8]

References

^ Noble C, Weihe Dalsgaard P, Stybe Johansen S, Linnet K (April 2018). "Application of a screening method for fentanyl and its analogues using UHPLC-QTOF-MS with data-independent acquisition (DIA) in MS^E mode and retrospective analysis of authentic forensic blood samples". Drug Testing and Analysis. 10 (4): 651–662. doi:10.1002/dta.2263. PMID 28834382.
^ Pierzynski HG (23 August 2017). "Tips for Interpreting GC-MS Fragmentation of Unknown Substituted Fentanyls". Cayman Chemical.
^ "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration. Archived from the original (PDF) on 2019-08-01. Retrieved 2019-08-01.
^ Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
^ Armenian P, Vo KT, Barr-Walker J, Lynch KL (May 2018). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review". Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317. S2CID 21404877.
^ Drug Enforecement Administration, Department of Justice (February 2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–5192. PMID 29932611.
^ "Notification detail. Government Decree amending Annex IV to the Government Decree on substances, preparations and plants to be classified as narcotics The following 9 new substances are classified: 4-chloro-isobutyrfentanyl, 4-Fluoro-isobutyrfentanyl, 3-phenylpropanoylfentanyl, benzodioxole fentanyl, benzoyl fentanyl, cyclopentyl fentanyl, cyclopropyl fentanyl, methoxyacetyl fentanyl and tetramethylcyclopropyane fentanyl". European Commission. 12 September 2017.
^ "14 nya ämnen kan klassas som narkotika eller hälsofarlig vara". The Public Health Agency of Sweden. 14 October 2017.

[1] Noble C, Weihe Dalsgaard P, Stybe Johansen S, Linnet K (April 2018). "Application of a screening method for fentanyl and its analogues using UHPLC-QTOF-MS with data-independent acquisition (DIA) in MS^E mode and retrospective analysis of authentic forensic blood samples". Drug Testing and Analysis. 10 (4): 651–662. doi:10.1002/dta.2263. PMID 28834382.

[2] Pierzynski HG (23 August 2017). "Tips for Interpreting GC-MS Fragmentation of Unknown Substituted Fentanyls". Cayman Chemical.

[3] "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration. Archived from the original (PDF) on 2019-08-01. Retrieved 2019-08-01.

[4] Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.

[pmid29042317-5] Armenian P, Vo KT, Barr-Walker J, Lynch KL (May 2018). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review". Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317. S2CID 21404877.

[pmid29932611-6] Drug Enforecement Administration, Department of Justice (February 2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–5192. PMID 29932611.

[7] "Notification detail. Government Decree amending Annex IV to the Government Decree on substances, preparations and plants to be classified as narcotics The following 9 new substances are classified: 4-chloro-isobutyrfentanyl, 4-Fluoro-isobutyrfentanyl, 3-phenylpropanoylfentanyl, benzodioxole fentanyl, benzoyl fentanyl, cyclopentyl fentanyl, cyclopropyl fentanyl, methoxyacetyl fentanyl and tetramethylcyclopropyane fentanyl". European Commission. 12 September 2017.

[8] "14 nya ämnen kan klassas som narkotika eller hälsofarlig vara". The Public Health Agency of Sweden. 14 October 2017.

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Side effects

Legal status

See also

References