Isofentanyl

Isofentanyl (3-methyl-benzylfentanyl) is an opioid analgesic that is an analog (and structural isomer) of fentanyl first invented in 1973,^[2] and which has been sold as a designer drug.^[3]

Isofentanyl

Legal status
Legal status	US: Schedule I[1]
Identifiers
IUPAC name N-(1-Benzyl-3-methylpiperidin-4-yl)-N-phenylpropanamide
CAS Number	79278-40-3 Y
PubChem CID	10449690
ChemSpider	8625107
UNII	BT57ARH9QX
CompTox Dashboard (EPA)	DTXSID00747120
Chemical and physical data
Formula	C22H28N2O
Molar mass	336.479 g·mol−1
3D model (JSmol)	Interactive image
SMILES c2ccccc2N(C(=O)CC)C1CCN(CC1C)Cc3ccccc3

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

As a structural isomer of fentanyl itself, isofentanyl is banned under drug analogue laws in many jurisdictions around the world. In the United States, fentanyl-related substances are Schedule I controlled substances.^[1]

See also

• 3-Methylfentanyl
• Benzylfentanyl
• α-Methylacetylfentanyl
• 4-Methylphenethylacetylfentanyl
• Homofentanyl
• Secofentanyl
• List of fentanyl analogues

References

1. Drug Enforcement Administration, Department of Justice (2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–92. PMID 29932611.
2. Riley TN, Hale DB, Wilson MC (June 1973). "4-Anilidopiperidine analgesics. I. Synthesis and analgesic activity of certain ring-methylated 1-substituted 4-propananilidopiperidines". Journal of Pharmaceutical Sciences. 62 (6): 983–6. doi:10.1002/jps.2600620627. PMID 4712637.
3. Meyer MR, Dinger J, Schwaninger AE, Wissenbach DK, Zapp J, Fritschi G, Maurer HH (January 2012). "Qualitative studies on the metabolism and the toxicological detection of the fentanyl-derived designer drugs 3-methylfentanyl and isofentanyl in rats using liquid chromatography-linear ion trap-mass spectrometry (LC-MS(n))". Analytical and Bioanalytical Chemistry. 402 (3): 1249–55. doi:10.1007/s00216-011-5528-8. PMID 22065349. S2CID 329682.
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): 626–31. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
5. Armenian P, Vo KT, Barr-Walker J, Lynch KL (October 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.