fentanyl

Also known as N-(1-phenethylpiperidin-4-yl)-N-phenylpropionamide, N-(1-phenethyl-4-piperidinyl)-N-phenylpropionamide, N-(1-phenethyl-4-piperidyl)propionanilide, 1-phenethyl-4-N-propionylanilinopiperidine, 1-phenethyl-4-(N-phenylpropionamido)piperidine, N-phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide, N-phenethyl-4-(N-propionylanilino)piperidine, 1-Phenethyl-4-(N-phenylpropionamido)piperidine

composto chimico

OverviewAI-generated

Fentanyl is a chemical compound with the formula C₂₂H₂₈N₂O. Its IUPAC name is N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide. The substance has a melting point of 83 and a median lethal dose (LD50) of 3.1. It possesses a mass of 336.220164 and a weight of 336.5. The compound is characterized by a charge of 0, an xlogp of 4, and a tpsa of 23.6. It contains 0 hydrogen bond donors and 2 hydrogen bond acceptors.

The canonical SMILES representation for fentanyl is CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3. It is associated with the MCN code 2933.33.63. A stylized version of its name is written as "fentaNYL".

In scientific literature, fentanyl is the subject of 32265 PubMed entries. Additionally, the compound is referenced by 1,947 other encyclopedia articles.

Synthesized by Vinony from 21 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 443760208
Drug.image: Fentanyl 2D-Skeletal.png
Drug.image2: Fentanyl 3D Ball-and-Stick.png
Drug.image_class2: bg-transparent
Drug.width2: 280
Drug.pronounce: /ˈfɛntəˌnɪl/
Drug.tradename: Actiq, Duragesic, Sublimaze, others
Drug.MedlinePlus: a605043
Drug.DailyMedID: Fentanyl
Drug.pregnancy_AU: C
Drug.dependency_liability: High
Drug.routes_of_administration: Buccal, epidural, intramuscular, intrathecal, intravenous, sublingual, transdermal
Drug.class: Opioid
Drug.ATC_prefix: N01
Drug.ATC_suffix: AH01
Drug.legal_AU: S8
Drug.legal_BR: Class A1

via Wikipedia infobox

Chemical data

Formula: C22H28N2O
Molecular weight: 336.5 g/mol
IUPAC name: N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
SMILES: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
InChIKey: PJMPHNIQZUBGLI-UHFFFAOYSA-N
XLogP: 4
Polar surface area: 23.6 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

32,265 papers

The anomalous pharmacology of fentanyl.ReviewBritish journal of pharmacology · 2023Kelly E, Sutcliffe K, Cavallo D et al.DOI: 10.1111/bph.15573
Fentanyl Absorption, Distribution, Metabolism, and Excretion: Narrative Review and Clinical Significance Related to Illicitly Manufactured Fentanyl.ReviewJournal of addiction medicine · 2023Bird HE, Huhn AS, Dunn KEDOI: 10.1097/ADM.0000000000001185
[Fentanyl].ReviewUgeskrift for laeger · 2025Vestergaard SV, Nielsen AVA, Hollingdal M et al.DOI: 10.61409/V01250023
The fentanyl story.The journal of pain · 2014Stanley THDOI: 10.1016/j.jpain.2014.08.010
Caring for Hospitalized Adults With Opioid Use Disorder in the Era of Fentanyl: A Review.ReviewJAMA internal medicine · 2024Englander H, Thakrar AP, Bagley SM et al.DOI: 10.1001/jamainternmed.2023.7282
Fentanyl Overdose.JAMA · 2023Walter KDOI: 10.1001/jama.2022.22462
Reasons to avoid fentanyl.ReviewAnnals of palliative medicine · 2020Davis MP, Behm BDOI: 10.21037/apm.2020.01.12
Detection of Fentanyl and Fentanyl Analogs.ReviewClinics in laboratory medicine · 2025Crews BODOI: 10.1016/j.cll.2025.01.012

via PubMed

Article · Italiano

Il fentanyl (noto anche come fentanil o fentanile, o con i nomi commerciali Dogetic, Sublimaze, Actiq, Durogesic, Duragesic, Fentanest, Effentora, Onsolis, Instanyl, Abstral e altri) è un analgesico, appartenente alla classe delle 4-anilidopiperidine, oppioide sintetico. Si tratta di un agonista forte del recettore μ per gli oppioidi; per contrastare i suoi effetti viene utilizzato il naloxone. Il fentanyl è circa 100 volte più potente della morfina: 100 μg di fentanyl equivalgono in attività analgesica approssimativamente a 30 mg di eroina e 125 mg di petidina, con una rapida insorgenza e breve durata d'azione. Storicamente è stato utilizzato per trattare il dolore cronico ed è comunemente usato come anestetico prima di interventi chirurgici o manovre invasive. Ha una LD50 di 3,1 mg/kg nei ratti e una LD50 di 0,03 mg/kg nelle scimmie.

Abstract from DBpedia / Wikipedia · CC BY-SA