Impact of conformational and solubility properties on psycho-activity of cannabidiol (CBD) and tetrahydrocannabinol (THC)
作者： Vitor A.N. Bragança , Tiago G. França , Ana C.S.P.S. de Jesus , Ivanete C. Palheta , Fernanda P.A. Melo
DOI: 10.1016/J.CDC.2020.100345
关键词: High energy 、 Quantum chemical 、 Cannabinoid 、 Steric effects 、 Tetrahydrocannabinol 、 Lipophilicity 、 Cannabidiol 、 Stereochemistry 、 Chemistry 、 Solubility
摘要: Abstract Cannabidiol (CBD) is one among many others identified bioactive cannabinoid derivatives. It the main component in Cannabis sativum oil and can be applied as potential therapeutic agent. has not any psychoactive effects such those caused by tetrahydrocannabinol (THC). The basic difference between CBD THC an opened or closed heterocycle ring. A conformational study using quantum chemical calculations was performed to DFT/B3LYP/6-31G(d,p) level. high energy barrier values, superior 20 kcal/ mol, may explain small ability of exhibit psychostimulant effect. This property controlled steric hindrance polar groups nonpolar moieties. n-Pentyl chain little influence on conformation CBD. search a simplified cannabidiol derivative showed that stereo-electronic repulsions are responsible for limitation conformations. have highest lipophilicity values when compared other agents central nervous system.
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