FENTANYL Chemical Properties
- Melting point:83-84°C
- Boiling point:466℃
- Density 1.087
- refractive index 1.6500 (estimate)
- Flash point:186℃
- storage temp. Controlled Substance, -20°C Freezer
- solubility Practically insoluble in water, freely soluble in ethanol (96 per cent) and in methanol
- pka8.4(at 25℃)
- color Crystals
- Water Solubility 0.2g/L(25 ºC)
- EPA Substance Registry SystemPropanamide, N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]- (437-38-7)
- Hazard Codes F,T
- Risk Statements 11-23/25-36/38-39/23/24/25-23/24/25
- Safety Statements 16-24-45-36/37-7
- RIDADR 1544
- WGK Germany 2
- RTECS UE5550000
- HazardClass 6.1(b)
- PackingGroup III
- HS Code 2933330000
- Hazardous Substances Data437-38-7(Hazardous Substances Data)
- ToxicityLD50 orl-rat: 18 mg/kg JPPMAB 25,929,73
FENTANYL Usage And Synthesis
- Chemical PropertiesPale Brown Solid
- OriginatorFentanyl,Janssen,W. Germany,1963
- UsesUsed as an analgesic. Controlled Substance
- DefinitionChEBI: The carboxamide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.
- Manufacturing ProcessTo the stirred solution of 5 parts of N-(4-piperidyl)propionanilide, 6.85 parts
sodium carbonate, 0.05 part potassium iodide in 120 parts hexone is added
portionwise a solution of 3.8 parts β-phenylethyl chloride in 24 parts 4-
methyl-2-pentanone. The mixture is stirred and refluxed for 27 hours. The
reaction mixture is filtered while hot, and the filtrate is evaporated. The oily
residue is dissolved in 160 parts diisopropyl ether and the solution is filtered
several times until clear, then concentrated to a volume of about 70 parts. The
residue is then cooled for about 2 hours at temperatures near 0°C to yield N-
[1-(β-phenylethyl)-4-piperidyl]propionanilide, melting at about 83° to 84°C as
described in US Patent 3,141,823.
The starting material is prepared by reacting 1-benzyl-4-piperidone with aniline, reducing the condensation product with lithium aluminum hydride, reacting the product thus obtained with propionic anhydride, then hydrogen.
- brand nameDuragesic (ALZA).
- Therapeutic FunctionNarcotic analgesic
- General DescriptionWhen the 4-phenyl substituent of meperidine was replaced with a 4-aniline with a nitrogen connection, the potency increased. This led to the development of the 4-anilidopiperidine series of compounds. Fentanyl (Sublimaze) was the first compound marketed and was found to be almost 500 times more potent than meperidine. The high lipophilicity of fentanyl gave it a quick onset, and the quick metabolism led to a short duration of action. The combination of potency, quick onset, and quick recovery led to the use of fentanyl as an adjunct anesthetic.
- Clinical UseFentanyl (Sublimaze) and its related phenylpiperidine
derivatives are extremely potent drugs.They are used as
adjuncts to anesthesia, and fentanyl may be given transdermally
as an analgesic and as an oral lozenge for the
induction of anesthesia, especially in children who may
become anxious if given IV anesthesia.
Fentanyl is 80 to 100 times as potent as morphine. Sufentanil (Sufenta) is 500- to 1,000-fold more potent than morphine, while alfentanil (Alfenta) is approximately 20 times more potent than morphine. Their onset of action is usually less than 20 minutes after administration. Dosage is determined by the lean body mass of the patient, since the drugs are lipophilic and tend to get trapped in body fat, which acts as a reservoir, prolonging their half-life. In addition, redistribution of the drugs from the brain to fat stores leads to a rapid offset of action. Droperidol, a neuroleptic agent, is generally administered in combination with fentanyl for IV anesthesia.
Fentanyl transdermal patches are available for analgesia in chronic pain and for postsurgical patients. The use of the patch is contraindicated, however, for patients immediately after surgery because of the profound respiratory depression associated with its use. The patches must be removed and replaced every 3 days. The onset of action of transdermal fentanyl is slower than that of oral morphine. Thus, patients may require the use of oral analgesics until therapeutic levels of fentanyl are achieved. Fentanyl lozenges have been used to induce anesthesia in children and to reduce pain associated with diagnostic tests or cancer in adult patients. However, all of the adverse side effects associated with morphine are produced with far greater intensity, but shorter duration, by fentanyl in the patch, the lozenge, or IV administration. Given the abuse liability of fentanyl, controversy exists as to the ethics of marketing a lollipop lozenge form.
Sufentanil is much more potent than fentanyl and is indicated specifically for long neurosurgical procedures. In such patients, sufentanil maintains anesthesia over a long period when myocardial and cerebral oxygen balance are critical.
- Side effectsIn addition to all of the adverse effects and contraindications
previously described for morphine, the following
contraindications apply specifically to these drugs.
They are contraindicated in pregnant women because
of their potential teratogenic effects. They also can
cause respiratory depression in the mother, which reduces
oxygenation of fetal blood, and in the newborn;
the incidence of sudden infant death syndrome (SIDS)
in the newborn is also increased.
Cardiac patients need to be monitored closely when receiving these drugs because of their bradycardiac effects (which can lead to ectopic arrhythmias), and hypotensive effects resulting from prolonged vasodilation. In addition, the drugs stiffen the chest wall musculature, an effect reversed by naloxone.
- Safety ProfilePoison by intraperitoneal routes. Human systemic effects by intravenous route: somnolence, respiratory depression. When heated to decomposition it emits toxic fumes of NOx.
- -Hydroxy Fentanyl,b-Hydroxy Fentanyl 4-PIPERIDINECARBOXYLIC ACID, 4-[(1-OXOPROPYL)PHENYLAMINO]-1-(2-PHENYLETHYL), SODIUM SALT Lofentanil N-(1-Phenethyl-4-piperidyl)propionanilide hydrochloride N-[1-[2-(4-HYDROXY-PHENYL)-ETHYL]-PIPERIDIN-4-YL]-N-PHENYL-PROPIONAMIDE Mefentanyl phenaridine Fentanyl isothiocyanate N-[1-(1-HYDROXY-2-PHENYL-ETHYL)-PIPERIDIN-4-YL]-N-PHENYL-PROPIONAMIDE 4-PIPERIDINECARBOXYLIC ACID, 4-[(1-OXOPROPYL)PHENYLAMINO]-1-(2-PHENYLETHYL), METHYL ESTER ETHANEDIOATE N-(1-ACETYL-2,3-DIHYDRO-(1H)-INDOL-5-YL)-N-[1-(2-PHENYLETHYL)PIPERIDIN-4-YL]CYCLOPROPYLCARBOXAMIDE FENTANYL FENTANYL DIHYDROGEN CITRATE,FENTANYL CITRATE,FENTANYL CITRATE SALT,FENTANYL CITRATE 100 UG PER ML*IN MEOH-T -BUOH METHA,FENTANYL CITRATE--DEA SCHEDULE II 4-PIPERIDINECARBOXYLIC ACID, 4-[(1-OXOPROPYL)PHENYLAMINO] N-[2-METHYL-1H-INDOL-5-YL]-N-[1-(2-PHENYLETHYL)PIPERIDIN-4-YL]PROPANAMIDE Ohmefentanyl FENTANYL CITRATE [N-METHYL 3H] p-Fluoro Fentanyl