title: The synthesis and preliminary pharmacological evaluation of 4-methyl fentanyl.
abstract: The synthesis of 4-methyl fentanyl, a prototype of a novel class of fentanyl analogues has been effected in 5 steps, starting from N-ethoxycarbonyl-4-piperidone (approximately 20% overall yield). In the key step, N-phenylation of secondary aliphatic amide intermediare was achieved by a novel reaction, using diphenyliodonium chloride for the phenyl group transfer. Preliminary pharmacological results indicate that 4-methyl fentanyl is a super potent narcotic analgesic, about four times more potent than fentanyl.
authors.affiliation: Faculty of Chemistry, University of Belgrade, FR Yugoslavia.
authors.forename: I V
authors.initials: IV
authors.lastname: Mićović
authors.forename: M D
authors.initials: MD
authors.lastname: Ivanović
authors.forename: S M
authors.initials: SM
authors.lastname: Vuckovic
authors.forename: M S
authors.initials: MS
authors.lastname: Prostran
authors.forename: L
authors.initials: L
authors.lastname: Dosen-Mićović
authors.forename: V D
authors.initials: VD
authors.lastname: Kiricojević
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D005283:Fentanyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship
chemical_list: D000701:Analgesics, Opioid; D005283:Fentanyl