Quaternary ammonium salt derivatives of allylphenols with peripheral analgesic effect
Mem. Inst. Oswaldo Cruz
;
86(supl.2): 133-136, 1991. ilus, tab
Article
in English
| LILACS
| ID: lil-623955
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).
Full text:
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Index:
LILACS (Americas)
Main subject:
Safrole
/
Eugenol
/
Ammonium Compounds
/
Quaternary Ammonium Compounds
/
Analgesics
Limits:
Animals
Language:
English
Journal:
Mem. Inst. Oswaldo Cruz
Journal subject:
Tropical Medicine
/
Parasitology
Year:
1991
Type:
Article
/
Congress and conference
Affiliation country:
Brazil
Institution/Affiliation country:
Universidade Federal de Minas Gerais/BR
/
Universidade de São Paulo/BR
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