Cyclopropylfentanyl

Cyclopropylfentanyl
Legal status
Legal status	BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class A; US: Schedule I; Illegal in the European Union;
Identifiers
	IUPAC name N-Phenyl-N-[1-(2-Phenylethyl)piperidin-4-yl]cyclopropanecarboxamide;
CAS Number	1169-68-2;
PubChem CID	137332271;
ChemSpider	81367233;
UNII	9R5A897QPI;
KEGG	C22757;
CompTox Dashboard (EPA)	DTXSID101036718 ;
Chemical and physical data
Formula	C23H28N2O
Molar mass	348.490 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC1C(=O)N(C2CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4;
	InChI InChI=1S/C23H28N2O/c26-23(20-11-12-20)25(21-9-5-2-6-10-21)22-14-17-24(18-15-22)16-13-19-7-3-1-4-8-19/h1-10,20,22H,11-18H2; Key:OIQSKDSKROTEMN-UHFFFAOYSA-N;

Cyclopropylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug.^[1]^[2] Between June and December 2017, a total of 78 cyclopropylfentanyl-related deaths with analytical confirmation in post-mortem samples were reported by various European countries.^[3]^[4] Another 115 deaths involving cyclopropylfentanyl were reported from the United States in 2017.^[5]

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.^[6] 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.^[7]

Legal status

Cyclopropylfentanyl was banned in Finland in September 2017,^[8] and in Sweden in October 2017.^[9] It is a Schedule I controlled drug in the USA since January 2018.^[10] In September 2018 the European Union subjected cyclopropylfentanyl to control measures.^[11]

References

^ Park K (20 December 2017). "2 arrested in drug scheme that funneled cyclopropyl fentanyl pills into Monmouth County". Asbury Park Press.
^ Edison L, Erickson A, Smith S, Lopez G, Hon S, King A, et al. (October 2017). "Notes from the Field: Counterfeit Percocet-Related Overdose Cluster - Georgia, June 2017". MMWR. Morbidity and Mortality Weekly Report. 66 (41): 1119–1120. doi:10.15585/mmwr.mm6641a6. PMC 5689089. PMID 29049275.
^ European Monitoring Centre for Drugs Drug Addiction; European Union Agency for Law Enforcement Cooperation (February 2018). Cyclopropylfentanyl : EMCDDA–Europol joint report on a new psychoactive substance : N-phenyl-N-1-(2-phenylethyl)piperidin-4-ylcyclopropanecarboxamide (cyclopropylfentanyl) : in accordance with Article 5 of Council Decision 2005/387/JHA on the information exchange, risk assessment and control of new psychoactive substances. Publications Office. doi:10.2810/06909. ISBN 9789294972545.
^ Wilde M, Sommer MJ, Auwärter V, Hermanns-Clausen M (March 2020). "Acute severe intoxication with cyclopropylfentanyl, a novel synthetic opioid". Toxicology Letters. 320: 109–112. doi:10.1016/j.toxlet.2019.11.025. PMID 31778775. S2CID 208356660.
^ "Schedules of Controlled Substances: Temporary Placement of Cyclopropyl Fentanyl in Schedule I". www.deadiversion.usdoj.gov. 4 January 2018.
^ 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.
^ "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". Notification detail. European Commission. 12 September 2017.
^ "14 nya ämnen kan klassas som narkotika eller hälsofarlig vara". The Public Health Agency of Sweden. 14 October 2017.
^ Drug Enforcement Administration, Department of Justice. (January 2018). "Schedules of Controlled Substances: Temporary Placement of Cyclopropyl Fentanyl in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (3): 469–472. PMID 29319947.
^ "Two new synthetic opioids to be placed under control across the EU". 28 September 2018.

[1] Park K (20 December 2017). "2 arrested in drug scheme that funneled cyclopropyl fentanyl pills into Monmouth County". Asbury Park Press.

[2] Edison L, Erickson A, Smith S, Lopez G, Hon S, King A, et al. (October 2017). "Notes from the Field: Counterfeit Percocet-Related Overdose Cluster - Georgia, June 2017". MMWR. Morbidity and Mortality Weekly Report. 66 (41): 1119–1120. doi:10.15585/mmwr.mm6641a6. PMC 5689089. PMID 29049275.

[3] European Monitoring Centre for Drugs Drug Addiction; European Union Agency for Law Enforcement Cooperation (February 2018). Cyclopropylfentanyl : EMCDDA–Europol joint report on a new psychoactive substance : N-phenyl-N-1-(2-phenylethyl)piperidin-4-ylcyclopropanecarboxamide (cyclopropylfentanyl) : in accordance with Article 5 of Council Decision 2005/387/JHA on the information exchange, risk assessment and control of new psychoactive substances. Publications Office. doi:10.2810/06909. ISBN 9789294972545.

[4] Wilde M, Sommer MJ, Auwärter V, Hermanns-Clausen M (March 2020). "Acute severe intoxication with cyclopropylfentanyl, a novel synthetic opioid". Toxicology Letters. 320: 109–112. doi:10.1016/j.toxlet.2019.11.025. PMID 31778775. S2CID 208356660.

[5] "Schedules of Controlled Substances: Temporary Placement of Cyclopropyl Fentanyl in Schedule I". www.deadiversion.usdoj.gov. 4 January 2018.

[6] 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.

[pmid29042317-7] 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.

[8] "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". Notification detail. European Commission. 12 September 2017.

[9] "14 nya ämnen kan klassas som narkotika eller hälsofarlig vara". The Public Health Agency of Sweden. 14 October 2017.

[10] Drug Enforcement Administration, Department of Justice. (January 2018). "Schedules of Controlled Substances: Temporary Placement of Cyclopropyl Fentanyl in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (3): 469–472. PMID 29319947.

[11] "Two new synthetic opioids to be placed under control across the EU". 28 September 2018.

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Side effects

Legal status

See also

References