title: Dialkylaminoalkylnaphthalenes as novel opioid-like analgesics.
abstract: The study of dialkylaminoalkylnaphthalenes as novel opioid-like analgesics is reported. In particular, the synthesis of (1R,2R/1S,2S)-1-ethyl-1-[2-(6-hydroxynaphthyl)]-1-hydrox-2-m ethyl-2-dimethylaminoethane and its structural analogue (1R,2R/1S,2S)-1-ethyl-1-[2-(6-fluoronaphthyl)]-1-hydroxy-2-methyl- 2-dimethylaminoethane and the configurational analysis by X-ray and 1H NMR spectroscopy are described. Pharmacological profiles are discussed on the basis of the experimental results of analgesia tests (hot plate and writhing test) and rota-rod test, which was performed to distinguish analgesia from drug-induced motor changes. The compounds showed dose-dependent antinociception, with less potency than morphine. Motor coordination appeared to be less involved.
authors.affiliation: Dipartimeto di Chimica Farmaceutica, Università di Pavia, Italy. collina@chifar.unipv.it
authors.forename: S
authors.initials: S
authors.lastname: Collina
authors.forename: O
authors.initials: O
authors.lastname: Azzolina
authors.forename: D
authors.initials: D
authors.lastname: Vercesi
authors.forename: F
authors.initials: F
authors.lastname: Benevelli
authors.forename: A
authors.initials: A
authors.lastname: Callegari
authors.forename: C
authors.initials: C
authors.lastname: Tadini
authors.forename: E
authors.initials: E
authors.lastname: Lanza
authors.forename: A
authors.initials: A
authors.lastname: Barbieri
authors.forename: V
authors.initials: V
authors.lastname: Ghislandi
mesh_terms: D000701:Analgesics, Opioid / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D000818:Animals; D002460:Cell Line; D018360:Crystallography, X-Ray; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D011869:Radioligand Assay; D011957:Receptors, Opioid / Q000378:metabolism; D013055:Spectrophotometry, Infrared
chemical_list: D000701:Analgesics, Opioid; D009281:Naphthalenes; D011957:Receptors, Opioid