Structural Formula Vector Image
Title: Fentanyl
CAS Registry Number: 437-38-7
CAS Name: N-Phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide
Additional Names: N-(1-phenethyl-4-piperidyl)propionanilide; N-(1-phenethyl-4-piperidinyl)-N-phenylpropionamide; phentanyl
Manufacturers' Codes: R-4263
Trademarks: Duragesic (J & J); Durogesic (J & J)
Molecular Formula: C22H28N2O
Molecular Weight: 336.47
Percent Composition: C 78.53%, H 8.39%, N 8.33%, O 4.76%
Literature References: Prepn: P. A. J. Janssen, FR 1344366; idem, US 3164600 (1963, 1965 both to Janssen). Pharmacology: J. F. Gardocki, J. Yelnosky, Toxicol. Appl. Pharmacol. 6, 48 (1964); R. Hess et al., J. Pharmacol. Exp. Ther. 179, 474 (1971). Effects on cerebral circulation and metabolism in rats: C. Carlsson et al., Anesthesiology 57, 375 (1982). Clinical studies: E. A. Welchew, J. A. Thornton, Anaesthesia 37, 309 (1982); M. J. Stephens et al., Med. J. Aust. 1, 419 (1982). Review of clinical experience with transdermal formulation: R. B. R. Muijsers, A. J. Wagstaff, Drugs 61, 2289-2307 (2001).
Properties: Crystals, mp 83-84°. Partition coefficient (n-octanol/water): 860. pKa 8.4.
Melting point: mp 83-84°
pKa: pKa 8.4
Log P: Partition coefficient (n-octanol/water): 860
Derivative Type: Citrate
CAS Registry Number: 990-73-8
Trademarks: Actiq (Cephalon); Fentanest (Pharmacia); Leptanal (Janssen-Cilag); Sublimaze (Janssen)
Molecular Formula: C22H28N2O.C6H8O7
Molecular Weight: 528.59
Percent Composition: C 63.62%, H 6.86%, N 5.30%, O 24.21%
Properties: Crystalline powder, mp 149-151°. Bitter taste. One gram dissolves in about 40 ml water. Sol in methanol; sparingly sol in chloroform. LD50 in mice (mg/kg): 11.2 i.v.; 62 s.c. (Gardocki, Yelnosky).
Melting point: mp 149-151°
Toxicity data: LD50 in mice (mg/kg): 11.2 i.v.; 62 s.c. (Gardocki, Yelnosky)
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic).
Therap-Cat-Vet: Analgesic; tranquilizer.
Keywords: Analgesic (Narcotic).

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