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Substance Name: Fentanyl [USAN:USP:INN:BAN]
RN: 437-38-7
UNII: UF599785JZ
InChIKey: PJMPHNIQZUBGLI-UHFFFAOYSA-N
Note
- A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078)
Molecular Formula
- C22-H28-N2-O
Molecular Weight
- 336.4762
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Adjuvants, Anesthesia
- Analgesic
- Analgesics
- Analgesics, Opioid
- Anesthetics
- Anesthetics, General
- Anesthetics, Intravenous
- Central Nervous System Agents
- Central Nervous System Depressants
- Drug / Therapeutic Agent
- Human Data
- Narcotics
- Peripheral Nervous System Agents
- Sensory System Agents
Superlist Classification Code
- DEA Schedule II
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Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
Names and Synonyms
Name of Substance
- Fentanyl
- Fentanyl [USAN:USP:INN:BAN]
MeSH Heading
- Fentanyl
Synonyms
- 1-Phenethyl-4-(N-phenylpropionamido)piperidine
- 1-Phenethyl-4-N-propionylanilinopiperidine
- 5-22-08-00049 (Beilstein Handbook Reference)
- BRN 0494484
- Duragesic
- Duragesic-100
- Duragesic-12
- Duragesic-25
- Duragesic-50
- Duragesic-75
- Durotep MT
- EINECS 207-113-6
- Fentanest
- Fentanil
- Fentanil [DCIT]
- Fentanila
- Fentanila [INN-Spanish]
- Fentanyl
- Fentanyl buccal
- Fentanyl Transdermal System
- Fentanyl-100
- Fentanyl-12
- Fentanyl-25
- Fentanyl-50
- Fentanyl-75
- Fentanylum
- Fentanylum [INN-Latin]
- Fentora
- HSDB 3329
- Ionsys
- JNS020QD
- Lazanda
- Matrifen
- N-(1-Phenethyl-4-piperidinyl)-N-phenylpropionamide
- N-(1-Phenethyl-4-piperidyl)propionanilide
- N-Phenethyl-4-(N-propionylanilino)piperidine
- N-Phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide
- PecFent
- Phentanyl
- R 4263
- Sentonil
- Sublimase
- Sublimaze
- Subsys
- UNII-UF599785JZ
Systematic Names
- Fentanyl
- N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionamide
- Propanamide, N-phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)- (9CI)
- Propionanilide, N-(1-phenethyl-4-piperidyl)-
Superlist Names
- DEA No. 9801
- Fentanyl
Registry Numbers
CAS Registry Number
- 437-38-7
FDA UNII
- UF599785JZ
Other Registry Number
- 80832-90-2
Related Registry Number
- 990-73-8 (citrate)
System Generated Number
- 0000437387
Structure Descriptors
InChI
InChI=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,2,13-18H2,1H3InChIKey
PJMPHNIQZUBGLI-UHFFFAOYSA-NSmiles
CCC(=O)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | intravenous | 2ug/kg (0.002mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | British Medical Journal. Vol. 1, Pg. 278, 1978. |
mouse | LD50 | intraperitoneal | 76mg/kg (76mg/kg) | BEHAVIORAL: EUPHORIA | Pharmaceutical Chemistry Journal Vol. 10, Pg. 1193, 1976. |
mouse | LD50 | intravenous | 2900ug/kg (2.9mg/kg) | Toksikologicheskii Vestnik. Vol. (4), Pg. 20, 1995. | |
mouse | LD50 | oral | 368mg/kg (368mg/kg) | Toksikologicheskii Vestnik. Vol. (4), Pg. 20, 1995. | |
mouse | LD50 | subcutaneous | 62mg/kg (62mg/kg) | Toksikologicheskii Vestnik. Vol. (4), Pg. 20, 1995. | |
rat | LD | intraspinal | > 10mg/kg (10mg/kg) | Acta Pharmacologica et Toxicologica. Vol. 56, Pg. 50, 1985. | |
rat | LD50 | intravenous | 2910ug/kg (2.91mg/kg) | Journal of Medicinal Chemistry. Vol. 17, Pg. 1047, 1974. | |
rat | LD50 | oral | 18mg/kg (18mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 25, Pg. 929, 1973. | |
rat | LD50 | subcutaneous | 1500ug/kg (1.5mg/kg) | Pharmaceutical Chemistry Journal Vol. 23, Pg. 395, 1989. | |
women | TDLo | oral | 100ug/kg (0.1mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Annals of Emergency Medicine. Vol. 35, Pg. 314, 2000. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 87.5 | deg C | EXP | |
log P (octanol-water) | 4.05 | (none) | EXP | |
Water Solubility | 200 | mg/L | 25 | EXP |
Vapor Pressure | 5.29E-09 | mm Hg | 25 | EST |
Henry's Law Constant | 9.20E-12 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 1.33E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.