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

Fentanyl is a highly potent synthetic opioid of the piperidine family, used primarily as pain medication. It is 50 to 100 times more potent than morphine. Its primary clinical use is in pain management for cancer patients and those recovering from surgery. Fentanyl is also used as a sedative for intubated patients. Fentanyl has a short duration of action. Fentanyl works by activating μ-opioid receptors. Brand names include Actiq, Duragesic, and Sublimaze, among others.

AI overview

Fentanyl is a powerful synthetic painkiller that is 50 to 100 times stronger than morphine and is primarily used to treat severe pain in cancer patients and people recovering from surgery. It matters because its extreme potency makes it effective for serious medical needs, but this same strength also makes it a significant public health concern when misused.

AI-generated from the Wikipedia summary — may 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

Show 8 more facts

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
MCN code: 2933.33.63
stylized name: fentaNYL

Sources (9)

via Wikidata · CC0

~49 min read

Article

46 sections

Contents

Medical uses
Anesthesia
Regional anesthesia
Obstetrics
Pain management
Chronic pain
Palliative care
Combat medicine
Breathing difficulties
Other
Adverse effects
Respiratory depression
Heart and blood vessels
Muscle rigidity
Wooden chest syndrome
Overdose
Prevention
Pharmacology
Classification
Structure-activity
Fentanyl analogs
Mechanism of action
Therapeutic effects
Detection in biological fluids
Detection for harm reduction purposes
Synthesis
Janssen
Siegfried
Gupta
Suh
History
Society and culture
Legal status
Recreational use
Enforcement
Brand names
Economics
Storage and disposal
State usage as weapon
US death penalty
Russian theater siege
Veterinary use
Notes
References
Further reading
External links

Fentanyl was first synthesized by Paul Janssen in 1960 and was approved for medical use in the United States in 1968. In 2015, were used in healthcare globally. , fentanyl was the most widely used synthetic opioid in medicine; in 2019, it was the 278th most commonly prescribed medication in the United States, with more than a million prescriptions. It is on the World Health Organization's List of Essential Medicines.