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fentanyl

File:Fentanyl.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ407541· pop 62· linked from 1,947 articles

fentanyl

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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.

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 Ų
H-bond donors
0
H-bond acceptors
2
Formal charge
0

via PubChem

Research

32,265 papers

via PubMed

~49 min read

Encyclopedic overview

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 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.

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.

Excerpted from Wikipedia’s “fentanyl” article, available under the CC BY-SA 4.0 licence.

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