An efficient, optimized synthesis of fentanyl and related analogs

The alternate and optimized syntheses of the parent opioid fentanyl and its analogs are described. The routes presented exhibit high-yielding transformations leading to these powerful analgesics after optimization studies were carried out for each synthetic step. The general three-step strategy prod...

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Bibliographic Details
Published in:PloS one 2014-09, Vol.9 (9), p.e108250-e108250
Main Authors: Valdez, Carlos A, Leif, Roald N, Mayer, Brian P
Format: Article
Language:English
Subjects:
acetylfentanyl
acetylthiofentanyl
Alkaloids
Alkylation
Analgesics
Analgesics, Opioid - chemical synthesis
Analogs
Anesthesiology
anhydrides
Biological & chemical weapons
Central nervous system depressants
chlorides
Citric acid
column chromatography
Drug dosages
ethers
Fentanyl
Fentanyl - analogs & derivatives
Fentanyl - chemical synthesis
Forensic sciences
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
Laboratories
Life sciences
methylenes
Narcotics
oils
Opioids
Optimization
Organic acids
Oxidation-Reduction
Pain
Physical Sciences
Salts
sublimaze
thiofentanyl
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Description
Summary:The alternate and optimized syntheses of the parent opioid fentanyl and its analogs are described. The routes presented exhibit high-yielding transformations leading to these powerful analgesics after optimization studies were carried out for each synthetic step. The general three-step strategy produced a panel of four fentanyls in excellent yields (73-78%) along with their more commonly encountered hydrochloride and citric acid salts. The following strategy offers the opportunity for the gram-scale, efficient production of this interesting class of opioid alkaloids.
ISSN:1932-6203
1932-6203
DOI:10.1371/journal.pone.0108250