Modulation of pharmacological profile of diphenylethane (lefetamine-type) derivatives.
With the aim to split the pharmacological properties of lefetamine (CAS 14148-99-3), some structural modifications of this compound have been studied. The basic group of lefetamine has been shifted from the alkyl chain to the vicinal phenyl ring and the N-substitution has been changed. The dimethylaminomethyl derivatives and chiefly the o-morpholinometyhl exhibited a strong anti-visceral chemical antinociception activity stripped of thermal antinociception properties and physical dependence liability. Furthermore, through the introduction of a diethylaminomethyl group in the lefetamine structure some derivatives were selected exhibiting besided a significant increase in the anti-visceral chemical antinociception activity, remarkable local anesthetic properties.
Carrara
M
M
Department of Pharmacology E. Meneghetti, University of Padova, Italy.
Zampiron
S
S
Pittarello
D
D
Cima
L
L
Rampa
A
A
Valenti
P
P
Da Re
P
P
Giusti
P
P
D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D000771:Anesthesia, Intravenous; D000779:Anesthetics, Local / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D000818:Animals; D001001:Anura; D001522:Behavior, Animal / Q000187:drug effects; D005260:Female; D006168:Guinea Pigs; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D010147:Pain Measurement / Q000187:drug effects; D010525:Peripheral Nerves / Q000187:drug effects; D010627:Phenethylamines / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D011817:Rabbits; D013329:Structure-Activity Relationship; D019966:Substance-Related Disorders / Q000523:psychology
D018712:Analgesics, Non-Narcotic; D000779:Anesthetics, Local; D010627:Phenethylamines; C011896:lephetamine