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Substance Name: Fentanyl citrate [USAN:USP:BAN:JAN]
RN: 990-73-8
UNII: MUN5LYG46H
InChIKey: IVLVTNPOHDFFCJ-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.C6-H8-O7

Molecular Weight

  • 528.5984
 

Classification Codes

Classification Codes

  • Analgesic (Narcotic)
  • Drug / Therapeutic Agent
  • Human Data

Superlist Classification Code

  • DEA Schedule II
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Names and Synonyms

Name of Substance

  • Fentanyl citrate [USAN:USP:BAN:JAN]

Synonyms

  • Abstral
  • Actiq
  • Duragesic
  • EINECS 213-588-0
  • Fentanyl citrate
  • Fentanyl citrate preservative free
  • Fentaz
  • Fentora
  • Lazanda
  • Leptanal
  • McN-JR 4263
  • McN-JR-4263-49
  • N-(1-Phenethyl-4-piperidinyl)propionanilide dihydrogen citrate
  • N-(1-Phenethyl-4-piperidyl)propionanilide citrate
  • N-(1-Phenethyl-4-piperidyl)propionanilide citrate (1:1)
  • N-(1-Phenethyl-4-piperidyl)propionanilide dihydrogen citrate
  • Onsolis
  • Oralet
  • Phentanyl citrate
  • R 5240
  • R-4263
  • Rapinyl
  • Sublimaze
  • Sublimaze preservative free
  • UNII-MUN5LYG46H

Systematic Names

  • Fentanyl dihydrogen citrate
  • Propanamide, N-phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)
  • Propionanilide, N-(1-phenethyl-4-piperidyl)-, citrate (1:1)

Superlist Name

  • DEA No. 9801

Mixture Name

  • Innovar

Registry Numbers

CAS Registry Number

  • 990-73-8

FDA UNII

  • MUN5LYG46H

Related Registry Number

  • 437-38-7 (Parent)

System Generated Number

  • 0000990738

Molecular Formulas

Molecular Formula

  • C22-H28-N2-O.C6-H8-O7

Molecular Formula Fragments

  • C22-H28-N2-O
  • C6-H8-O7
  • COMPONENT

Structure Descriptors

InChI

1S/C22H28N2O.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-12,21H,2,13-18H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

InChIKey

IVLVTNPOHDFFCJ-UHFFFAOYSA-N

Smiles

CCC(=O)N(C1CCN(CCc2ccccc2)CC1)c3ccccc3.OC(=O)CC(O)(CC(=O)O)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 15ug/kg/7M-C (0.015mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: REGIDITY

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Anesthesiology. Vol. 78, Pg. 629, 1993.
mouse LD50 intraperitoneal 68400ug/kg (68.4mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 535, 1979.
mouse LD50 intravenous 10100ug/kg (10.1mg/kg)   Drugs in Japan Vol. 6, Pg. 666, 1982.
mouse LD50 oral 368mg/kg (368mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 535, 1979.
mouse LD50 subcutaneous 62mg/kg (62mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 6, Pg. 48, 1964.
rat LD50 intraperitoneal 2070ug/kg (2.07mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 535, 1979.
rat LD50 intravenous 990ug/kg (0.99mg/kg)   Drugs in Japan Vol. 6, Pg. 666, 1982.
rat LD50 oral 18mg/kg (18mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous 5460ug/kg (5.46mg/kg)   Drugs in Japan Vol. 6, Pg. 666, 1982.