Abstract: An antioxidant mechanism of tetrahydrocannabinol (THC) and cannabidiol (CBD) were compared with a simplified model of α-tocopherol, butylhydroxytoluene and hydroxytoluene in order to understand the antioxidant nature of THC and CBD molecules using DFT. The following electronic properties were evaluated: frontier orbitals nature, ionization potential, O-H bond dissociation energy (BDEOH), stabilization energy, and spin density distribution. An important factor that shows an influence in the antioxidant property of THC is the electron abstraction at the phenol position. Our data indicate that the decrease of the HOMO values and the highest ionization potential values are related to phenol, ether, and alkyl moieties. On the other hand, BDEOH in molecules with the cyclohexenyl group at ortho position of phenol are formed from lower energies than the molecules with an ether group at the meta position. In the light of our results, the properties calculated here predict that THC has a sightly higher antioxidant potential than CBD.
Keywords: SAR; antioxidant; DFT; cannabinoids; CBD; electronic; THC
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Borges, R.S.; Batista, J., Jr.; Viana, R.B.; Baetas, A.C.; Orestes, E.; Andrade, M.A.; Honório, K.M.; da Silva, A.B.F. Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants. Molecules 2013, 18, 12663-12674.
Borges RS, Batista J, Jr, Viana RB, Baetas AC, Orestes E, Andrade MA, Honório KM, da Silva ABF. Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants. Molecules. 2013; 18(10):12663-12674.
Borges, Rosivaldo S.; Batista, João, Jr.; Viana, Rommel B.; Baetas, Ana C.; Orestes, Ednilsom; Andrade, Marcieni A.; Honório, Káthia M.; da Silva, Albérico B.F. 2013. "Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants." Molecules 18, no. 10: 12663-12674.