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

composé chimique

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

Wikidata facts

Mass: 336.220164
Has use: analgesic

Show 14 more facts

medical condition treated: arthritis
significant drug interaction: primidone
chemical formula: C₂₂H₂₈N₂O
Commons category: Fentanyl
melting point: 83
median lethal dose (LD50): 0.03
canonical SMILES: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
World Health Organisation international non-proprietary name: fentanyl
discoverer or inventor: Paul Janssen
subject has role: essential medicine
MCN code: 2933.33.63
topic's main category: Category:Fentanyl
legal status (medicine): boxed warning
stylized name: fentaNYL

Sources (9)

via Wikidata · CC0

Article · Français

Le fentanyl (R5240, sel citrique) est une drogue à propriété analgésique opioïde, synthétisée pour la première fois par le docteur Paul Janssen (Janssen Pharmaceutica) en Belgique vers la fin des années 1950. Son potentiel analgésique vaut environ 100 fois celui de la morphine et 50 fois celui de l'héroïne. Le fentanyl est dans la plupart des pays une substance réglementée assimilée aux stupéfiants, et se trouve au cœur de la crise américaine des opioïdes depuis les années 2010. Le fentanyl a été introduit dans la pratique médicale dans les années 1960 sous forme d'anesthésique intraveineux. À l'état gazeux, il a une odeur caractéristique d'orange. Le fentanyl a une dose létale médiane (DL50) de 3,1 mg/kg chez les rats et de 0,03 mg/kg chez les chimpanzés. La DL50 chez l’humain n'est pas connue avec précision mais est estimée à environ 2 mg. La dose mortelle minimale chez les humains est de 0,25 mg.

Abstract from DBpedia / Wikipedia · CC BY-SA