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Quaternary ammonium salt derivatives of allylphenols with peripheral analgesic effect
Oliveira, A. B de; Silva, T. H. A; Ferreira, S. H; Lorenzetti, B. B.
Afiliación
  • Oliveira, A. B de; Universidade Federal de Minas Gerais. ICEx. Departamento de Química. Belo Horizonte. BR
  • Silva, T. H. A; Universidade Federal de Minas Gerais. Faculdade de Farmácia. Departamento de Produtos Farmacêuticos. Belo Horizonte. BR
  • Ferreira, S. H; Universidade de São Paulo. Faculdade de Medicina de Ribeirão Preto. Ribeirão Preto. BR
  • Lorenzetti, B. B; Universidade de São Paulo. Faculdade de Medicina de Ribeirão Preto. Ribeirão Preto. BR
Mem. Inst. Oswaldo Cruz ; 86(supl.2): 133-136, 1991. ilus, tab
Article en En | LILACS | ID: lil-623955
Biblioteca responsable: BR1.1
ABSTRACT
Ammonium salt derivatives of natural allylphenols were synthesized with the purpose of obtaining potential peripheral analgesics. These drugs, by virtue of their physicochemical properties, would not be able to cross the blood brain barrier. Their inability to enter into the central nervous system (CNS) should prevent several adverse effects observed with classical opiate analgesics (Ferreira et al., 1984). Eugenol (1) O-methyleugenol (5) and safrole (9) were submitted to nitration, reduction and permethylation, leading to the ammonium salts 4, 8 and 12. Another strategy applied to eugenol (1), consisting in its conversion to a glycidic ether (13), opening the epoxide ring with secondary amines and methylation, led to the ammonium salts 16 and 17. All these ammonium salts showed significant peripheral analgesic action, in modified version of the Randall-Sellito test (Ferreira et al. 1978), at non-lethal doses. The ammonium salt 8 showed an activity comparable to that of methylnalorphinium, the prototype of an ideal peripheral analgesic (Ferreira et al., 1984).
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Texto completo: 1 Índice: LILACS Asunto principal: Safrol / Eugenol / Compuestos de Amonio / Compuestos de Amonio Cuaternario / Analgésicos Límite: Animals Idioma: En Revista: Mem. Inst. Oswaldo Cruz Asunto de la revista: MEDICINA TROPICAL / PARASITOLOGIA Año: 1991 Tipo del documento: Article / Congress and conference

Texto completo: 1 Índice: LILACS Asunto principal: Safrol / Eugenol / Compuestos de Amonio / Compuestos de Amonio Cuaternario / Analgésicos Límite: Animals Idioma: En Revista: Mem. Inst. Oswaldo Cruz Asunto de la revista: MEDICINA TROPICAL / PARASITOLOGIA Año: 1991 Tipo del documento: Article / Congress and conference