Síntese do (+)-canabidiol e avaliação de seu efeito ansiolítico
Data
2024-09-06
Autores
Rosa, Kawana 
Orientadores
Raminelli, Cristiano
Tipo
Dissertação de mestrado
Título da Revista
ISSN da Revista
Título de Volume
Resumo
(-)-Canabidiol [(-)-(CBD)] é um fitocanabinoide terpenofenólico, presente em diferentes espécies da planta Cannabis sativa, que apresenta um amplo potencial terapêutico, porém, devido às políticas antidrogas, seu consumo e venda são proibidos em diversos países. Neste contexto, realizamos o síntese do (+)-canabidiol [(+)-CBD], o enantiômero não natural do CBD, substância envolvida em um número limitado de estudos farmacológicos. A (S)-(+)-carvona foi utilizada como material de partida para a síntese do (+)-CBD, obtido por meio de uma reaçãode Friedel-Crafts, altamente diasterosseletiva, catalisada por triflato de prata (AgOTf). O (+)-CBD foi sintetizado em 6 etapas com um rendimento global de 3,2%. Estudos farmacológicos utilizando o método de esquiva discriminativa no labirinto em cruz (PM-DAT), como modelo para avaliar efeitos do tipo ansiolítico e de memória, foram desenvolvidoscom camundongos machos jovens e idosos. Nossos dados sugerem que o (+)-CBD apresenta efeito ansiolítico em camundongos idosos na dose de 20 mg/kg, quando comparado ao tratamento com diazepam (1 mg/kg).
(-)-Cannabidiol [(-)-(CBD)] is a terpenophenolic phytocannabinoid, present in different species of the Cannabis sativa plant, which has a broad therapeutic potential, however, due to anti-drugs policies, its consumption and sale are prohibited in several countries. In this context, we carried out the synthesis of (+)-cannabidiol [(+)-CBD], the non-natural enantiomer of CBD, substance involved in a limited number of pharmacological studies. (S)-(+)-Carvone has been used as a starting material for the synthesis of (+)-CBD, obtained through a highly diastereoselective Friedel-Crafts reaction, catalyzed by silver triflate (AgOTf). (+)-CBD was synthesized in 6 steps with an overall yield of 3.2%. Pharmacological studies using the plus-maze discriminative avoidance task (PM-DAT), as a model to evaluate anxiolytic-like and memory effects, were developed with young and aged male mice. Our data suggest that (+)-CBD at a dose of 20 mg/kg has an anxiolytic effect in aged mice compared to treatment with diazepam (1 mg/kg).
(-)-Cannabidiol [(-)-(CBD)] is a terpenophenolic phytocannabinoid, present in different species of the Cannabis sativa plant, which has a broad therapeutic potential, however, due to anti-drugs policies, its consumption and sale are prohibited in several countries. In this context, we carried out the synthesis of (+)-cannabidiol [(+)-CBD], the non-natural enantiomer of CBD, substance involved in a limited number of pharmacological studies. (S)-(+)-Carvone has been used as a starting material for the synthesis of (+)-CBD, obtained through a highly diastereoselective Friedel-Crafts reaction, catalyzed by silver triflate (AgOTf). (+)-CBD was synthesized in 6 steps with an overall yield of 3.2%. Pharmacological studies using the plus-maze discriminative avoidance task (PM-DAT), as a model to evaluate anxiolytic-like and memory effects, were developed with young and aged male mice. Our data suggest that (+)-CBD at a dose of 20 mg/kg has an anxiolytic effect in aged mice compared to treatment with diazepam (1 mg/kg).