4-Phenylfentanyl

4-Phenylfentanyl

Systematic (IUPAC) name
N-(1-phenethyl-4-phenyl-4-piperidyl)-N-phenyl-propanamide
Identifiers
ATC code	none
PubChem	CID 10319503
ChemSpider	8494967
Synonyms	4-Phenylfentanyl
Chemical data
Formula	C28H32N2O
Molar mass	412.565 g/mol
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
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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 8x 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.^[1]

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.^[2]

References

1. Kudzma LV, Severnak SA, Benvenga MJ, Ezell EF, Ossipov MH, Knight VV, Rudo FG, Spencer HK, Spaulding TC (December 1989). "4-Phenyl- and 4-heteroaryl-4-anilidopiperidines. A novel class of analgesic and anesthetic agents". Journal of Medicinal Chemistry 32 (12): 2534–42. doi:10.1021/jm00132a007. PMID 2585442.
2. Jane Mounteney, Isabelle Giraudon, Gleb Denissov, Paul Griffiths (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe.". The international journal of drug policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.