Structure via PubChem · Public domain (PubChem)
4-phenylfentanyl
Sign in to save4-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.
Chemical data
- Formula
- C28H32N2O
- Molecular weight
- 412.6 g/mol
- IUPAC name
- N-phenyl-N-[4-phenyl-1-(2-phenylethyl)piperidin-4-yl]propanamide
- SMILES
- CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4
- InChIKey
- BXCJXJLHYMWMQU-UHFFFAOYSA-N
- XLogP
- 5.6
- Polar surface area
- 23.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 412.251464
Show 3 more facts
- chemical formula
- C₂₈H₃₂N₂O
- canonical SMILES
- CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4
- Commons category
- 4-Phenylfentanyl
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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.
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.
Excerpted from Wikipedia’s “4-phenylfentanyl” article, available under the CC BY-SA 4.0 licence.