Isobutyrylfentanyl

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]

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
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC23H30N2O
Molar mass350.506 g·mol−1
3D model (JSmol)
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

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]

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

See also

References
  1. Giorgetti, Arianna; Centola, Carmela; Giorgetti, Raffaele (2017). "Fentanyl novel derivative-related deaths". Human Psychopharmacology: Clinical and Experimental. 32 (3): e2605. doi:10.1002/hup.2605. ISSN 0885-6222. PMID 28635020.
  2. Higashikawa, Yoshiyasu; Suzuki, Shinichi (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. Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (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.
  5. Armenian P, Vo KT, Barr-Walker J, Lynch KL (2017). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review" (PDF). 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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