4-Phenylfentanyl

Not to be confused with Phenylfentanyl or 3-Phenylpropanoylfentanyl.

4-Phenylfentanyl is an opioid analgesic that is a derivative of fentanyl. It was developed during the course of research that ultimately resulted in super-potent opioid derivatives such as carfentanil, though it is a substantially less potent analogue. 4-Phenylfentanyl is around eight times the potency of fentanyl in analgesic tests on animals, but more complex 4-heteroaryl derivatives such as substituted thiophenes and thiazoles are more potent still, as they are closer bioisosteres to the 4-carbomethoxy group of carfentanil.^[2]

4-Phenylfentanyl

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule I UK: Class A US: Schedule I[1]
Identifiers
IUPAC name N-Phenyl-N-[4-phenyl-1-(2-phenylethyl)piperidin-4-yl]propanamide
CAS Number	120448-97-7
PubChem CID	10319503
DrugBank	DB09168 Y
ChemSpider	8494967
UNII	L9P31JAO37
CompTox Dashboard (EPA)	DTXSID001018402
Chemical and physical data
Formula	C28H32N2O
Molar mass	412.577 g·mol−1
3D model (JSmol)	Interactive image
SMILES c3ccccc3CCN(CC2)CCC2(c1ccccc1)N(C(=O)CC)c4ccccc4
InChI InChI=1S/C28H32N2O/c1-2-27(31)30(26-16-10-5-11-17-26)28(25-14-8-4-9-15-25)19-22-29(23-20-28)21-18-24-12-6-3-7-13-24/h3-17H,2,18-23H2,1H3 Key:BXCJXJLHYMWMQU-UHFFFAOYSA-N
(verify)

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.^[3]

References

1. 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.
2. Kudzma LV, Severnak SA, Benvenga MJ, Ezell EF, Ossipov MH, Knight VV, et al. (December 1989). "4-Phenyl- and 4-heteroaryl-4-anilidopiperidines. A novel class of analgesic and anesthetic agents". Journal of Medicinal Chemistry. 32 (12): 2534–2542. doi:10.1021/jm00132a007. PMID 2585442.
3. 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.