Isobutyrylfentanyl

Isobutyrylfentanyl
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class A; US: Schedule I;
Identifiers
	IUPAC name 2-methyl-N-phenyl-N-[1-(1-phenylpropan-2-yl)piperidin-4-yl]propanamide;
CAS Number	119618-70-1;
PubChem CID	14402357;
ChemSpider	10551382;
UNII	LF0F3A39RV;
Chemical and physical data
Formula	C23H30N2O
Molar mass	350.506 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)C(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3;
	InChI InChI=1S/C23H30N2O/c1-19(2)23(26)25(21-11-7-4-8-12-21)22-14-17-24(18-15-22)16-13-20-9-5-3-6-10-20/h3-12,19,22H,13-18H2,1-2H3; Key:WRPFPNIHTOSMKU-UHFFFAOYSA-N;

Isobutyrylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug.^[1] It is believed to be around the same potency as butyrfentanyl^[2] but has been less widely distributed on illicit markets, though it was one of the earliest of the "new wave" of fentanyl derivatives to appear, and was reported in Europe for the first time in December 2012.^[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

Isobutyrylfentanyl is a Schedule I controlled drug in the USA since 1 February 2018.^[6]

References

^ Giorgetti A, Centola C, Giorgetti R (May 2017). "Fentanyl novel derivative-related deaths". Human Psychopharmacology. 32 (3): e2605. doi:10.1002/hup.2605. PMID 28635020.
^ Higashikawa Y, Suzuki S (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. S2CID 22092512.
^ Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA
^ 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.
^ "Schedules of Controlled Substances: Temporary Placement of Seven Fentanyl-Related Substances in Schedule I". Federal Register. 1 February 2018.

[GiorgettiCentola2017-1] Giorgetti A, Centola C, Giorgetti R (May 2017). "Fentanyl novel derivative-related deaths". Human Psychopharmacology. 32 (3): e2605. doi:10.1002/hup.2605. PMID 28635020.

[HigashikawaSuzuki2008-2] Higashikawa Y, Suzuki S (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. S2CID 22092512.

[3] Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA

[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.

[6] "Schedules of Controlled Substances: Temporary Placement of Seven Fentanyl-Related Substances in Schedule I". Federal Register. 1 February 2018.

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Side effects

Legal status

See also

References