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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
 

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

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

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

InChIKey

PJMPHNIQZUBGLI-UHFFFAOYSA-N

Smiles

CCC(=O)N(C1CCN(CCc2ccccc2)CC1)c3ccccc3

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.