f
fentanyl
Synthetic piperidine opioid used as an analgesic
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
- Formula
- C₂₂H₂₈N₂O
1
- C₂₂H₂₈N₂O
- Mass
- 336.2202 Da
1
- 336.2202 Da
- Melting point
- 83°C
Overview
Chemistry
All data
247 statements · 60% with external sources · numbers in brackets are citations
- Significant drug interaction
- isocarboxazid
- phenelzine
- procarbazine
- (±)-deprenyl
- amiodarone
- (RS)-methadone side effect: sinus bradycardia
- remifentanil side effect: sinus bradycardia
- alfentanil side effect: sinus bradycardia
Show 52 moreShow less
- sufentanil side effect: sinus bradycardia
- pethidine side effect: depressed level of consciousness
- pethidine side effect: central respiratory depression
- tramadol side effect: depressed level of consciousness
- tramadol side effect: central respiratory depression
- (RS)-methadone side effect: depressed level of consciousness
- (RS)-methadone side effect: central respiratory depression
- morphine side effect: depressed level of consciousness
- morphine side effect: central respiratory depression
- oxycodone side effect: depressed level of consciousness
- oxycodone side effect: central respiratory depression
- hydromorphone side effect: depressed level of consciousness
- hydromorphone side effect: central respiratory depression
- dihydrocodeine side effect: depressed level of consciousness
- dihydrocodeine side effect: central respiratory depression
- codeine side effect: depressed level of consciousness
- codeine side effect: central respiratory depression
- remifentanil side effect: depressed level of consciousness
- remifentanil side effect: central respiratory depression
- tapentadol side effect: depressed level of consciousness
- tapentadol side effect: central respiratory depression
- alfentanil side effect: depressed level of consciousness
- alfentanil side effect: central respiratory depression
- sufentanil side effect: depressed level of consciousness
- sufentanil side effect: central respiratory depression
- (±)-promethazine side effect: paralytic ileus
- (±)-promethazine side effect: depressed level of consciousness
- (±)-promethazine side effect: central respiratory depression
- pimozide side effect: paralytic ileus
- pimozide side effect: depressed level of consciousness
- pimozide side effect: central respiratory depression
- fluphenazine side effect: paralytic ileus
- fluphenazine side effect: depressed level of consciousness
- fluphenazine side effect: central respiratory depression
- (RS)-hydroxyzine side effect: paralytic ileus
- (RS)-hydroxyzine side effect: depressed level of consciousness
- (RS)-hydroxyzine side effect: central respiratory depression
- olanzapine side effect: paralytic ileus
- olanzapine side effect: depressed level of consciousness
- olanzapine side effect: central respiratory depression
- loxapine side effect: paralytic ileus
- loxapine side effect: depressed level of consciousness
- loxapine side effect: central respiratory depression
- chlorpromazine side effect: paralytic ileus
- chlorpromazine side effect: depressed level of consciousness
- chlorpromazine side effect: central respiratory depression
- chlorpheniramine side effect: paralytic ileus
- imipramine side effect: paralytic ileus
- clomipramine side effect: paralytic ileus
- itraconazole side effect: depressed level of consciousness
- itraconazole side effect: central respiratory depression
- levomepromazine side effect: depressed level of consciousness
- Medical condition treated
- pain
1
- osteoarthritis susceptibility 1
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- migraine
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- fibromyalgia
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- arthritis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- Complex Regional Pain Syndrome
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- peripheral neuropathy
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- pain
- Median lethal dose (LD50)
- 3.1 milligram per kilogram applies to taxon: laboratory rat · route of administration: unknown
- 0.03 milligram per kilogram applies to taxon: monkey · route of administration: unknown
- Canonical SMILES
- CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
1
- CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
- Active ingredient in
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- Subsys
1
- Subsys
- MCN code
- 2933.33.63
- Safety classification and labelling
- NFPA 704: Standard System for the Identification of the Hazards of Materials for Emergency Response nfpa health: 4 · nfpa fire: 1 · nfpa instability: 0
1
Sources- 1.cdc.gov/niosh/ershdb/emergencyresponsecard_29750022.htmlRetrieved 2018-05-05
- NFPA 704: Standard System for the Identification of the Hazards of Materials for Emergency Response nfpa health: 4 · nfpa fire: 1 · nfpa instability: 0
- Physically interacts with
- Opioid receptor delta 1 subject has role: agonist
1
- opioid receptor kappa 1 subject has role: agonist
1
- opioid receptor mu 1 subject has role: agonist
1
- Opioid receptor delta 1 subject has role: agonist
- LiverTox likelihood score
- LiverTox toxicity likelihood category E
1
Sources- 1.Stated in LiverToxncbi.nlm.nih.gov/books/n/livertox/FentanylAndAnaloguesRetrieved 2021-04-08
- LiverTox toxicity likelihood category E
- Stylized name
- fentaNYL has characteristic: Tall Man lettering · issued by: Institute for Safe Medication Practices
1
Sources- 1.ismp.org/recommendations/tall-man-letters-listRetrieved 2022-09-02
- fentaNYL has characteristic: Tall Man lettering · issued by: Institute for Safe Medication Practices
- Legal status (medicine)
- boxed warning
1
Sources- 1.“FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.”nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802
- boxed warning
- Substance control status
- Schedule II (Russia) applies to jurisdiction: Russia
1
Sources- 1.Stated in Government Decree No. 681 of 30 June 1998 (Russia)consultant.ru/document/cons_doc_LAW_19243/Retrieved 2026-08-31
- Schedule 8 (Australia) applies to jurisdiction: Australia
- Schedule I (Canada) applies to jurisdiction: Canada
- Anlage III (Germany) applies to jurisdiction: Germany
- Class A (United Kingdom) applies to jurisdiction: United Kingdom
- Schedule II (United States) applies to jurisdiction: United States
- Schedule I (Single Convention 1961)
- Schedule II (Russia) applies to jurisdiction: Russia
On other databases
60 identifiers linking fentanyl across the web's reference databases
- ATC codeN02AB03
- BBC News topic IDcd64ddx6g9zt
- BBC Things IDba51dadc-67e7-4f48-9be1-191b7798018e
- CAS Registry Number437-38-7
- ChEBI ID119915
- ChEMBL IDCHEMBL596
- ChemSpider ID3228
- DeCS ID28037
- DrugBank IDDB00813
- DrugCentral ID1164
- DSSTOX compound identifierDTXCID103049
- DSSTox substance IDDTXSID9023049
- EC number207-113-6
- ECHA Substance Infocard ID100.006.468
- Electronic Essential Medicines List medicine ID17
- Encyclopædia Britannica Online IDscience/fentanyl
- Encyclopedia of China (Third Edition) ID (2026)4V6pvn
- Encyclopedia of China (Third Edition) old ID (2021)141489
- Freebase ID/m/011w3r
- Guide to Pharmacology Ligand ID1626
- HSDB ID3329
- Human Metabolome Database IDHMDB0014951
- IEDB Epitope ID153507
- IMDb keywordfentanyl
- InChIInChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3
- InChIKeyPJMPHNIQZUBGLI-UHFFFAOYSA-N
- J9U entity ID987007529002805171
- KBpedia IDFentanyl
- KEGG IDD00320
- Library of Congress Authorities IDsh85047807
- LiverTox IDFentanylAndAnalogues
- MassBank accession IDMSBNK-Athens_Univ-AU154501
- MedlinePlus drug identifiera605043
- Merck Index monographm5298
- MeSH descriptor IDD005283
- MeSH tree codeD03.383.621.265
- Microsoft Academic ID (discontinued)2781072394
- Namuwiki ID펜타닐
- NDF-RT IDN0000147049
- OpenAlex IDC2781072394
- PDB ligand ID7V7
- Probes And Drugs IDPD009706
- PubChem CID3345
- Reaxys registry number494484
- RxNorm CUI4337
- ScienceDirect topic IDbiochemistry-genetics-and-molecular-biology/fentanyl
- SPLASHsplash10-000i-0209000000-d550d803c25d31570227
- Store medisinske leksikon IDfentanyl
- SureChEMBL ID8804
- The Guardian topic IDsociety/fentanyl
- Treccani's Dizionario di Medicina IDfentanyl
- UK Parliament thesaurus ID438805
- UN Thesaurus ID1002291
- UniChem compound ID450978
- UNIIUF599785JZ
- Wellcome Collection concept IDbgz8nq8t
- WikiKids IDFentanyl
- WikiProjectMed IDFentanyl
- Yale LUX IDconcept/bad36f8f-7a1f-4841-a5b7-8590d612261f
- YSO ID11906