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. 2013 Oct 14;18(10):12663-74.
doi: 10.3390/molecules181012663.

Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants

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Free PMC article

Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants

Rosivaldo S Borges et al. Molecules. .
Free PMC article

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.

Figures

Figure 1
Figure 1
Structures of tetrahydrocannabinol (THC) and cannabidiol (CBD).
Figure 2
Figure 2
Structure of simplified model of tetrahydrocannabinol (THC) and classical antioxidants.
Figure 3
Figure 3
Optimized structures of the neutral molecules.
Figure 4
Figure 4
HOMO and LUMO of tetrahydrocannabinol (THC) and cannabidiol (CBD).
Figure 5
Figure 5
Molecular electrostatic potential (MEP) surface of cannabinoid derivatives.
Figure 6
Figure 6
Spin densities in the cation free-radical of cannabinoid derivatives.
Figure 7
Figure 7
Structure of tetrahydrocannabinol (THC) and cannabidiol (CBD).

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