File:Fentanyl.svg · Wikimedia Commons · See Wikimedia Commons
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
強效的類鴉片止痛劑
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.
In the Vinony graph
Vinony's link graph records 1,947 inbound references to 芬太尼, and connects out to drug liberalization, epidural anesthesia and dyspnea.
It sits within the topics Analgesics, Anilides and Belgian inventions.
Vinony links it to 63 Wikipedia language editions.
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 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1968
- Admin. routes
- oral, parenteral, topical
- Indications
- pain, adenoma, subarachnoid hemorrhage, morbid obesity
via ChEMBL · EBI
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 · 中文
芬太尼（英语：Fentanyl）是一種強效的類鴉片止痛劑，起效迅速而作用時間極短。它是腦中的強力激動劑。芬太尼比嗎啡效力高50至100倍。但一些為了模擬芬太尼之藥理作用的芬太尼類似物可能比嗎啡高出10,000倍 ，如 。如過量使用，嚴重者將會引發呼吸困難死亡。
Abstract from DBpedia / Wikipedia · CC BY-SA
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