<p>Synthetic and retrosynthetic analysis together group additivity and experiment have been used to estimate the vaporization enthalpies of a series of cannabinoids. The cannabinoids include Δ<sup>8</sup>-tetrahydrocannabinol (Δ<sup>8</sup> -THC), Δ<sup>9</sup>-tetrahydrocannabinol (Δ<sup>9</sup> -THC), cannabidiol (CBD), cannabigerol (CBG), cannabichromene (CBC), and four homologs of Δ<sup>9</sup> -THC, CBD, CBG, and CBC: tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), and cannabigeroverin (CBGV), and cannabichromevarin (CBCV), respectively. Several new group properties have been derived from existing group values and also from the literature to complete previous estimations of both Δ<sup>9</sup> -THC and Δ<sup>8</sup> -THC reported earlier. The additional group values supplement those reported previously by Guthrie and Taylor. In addition, the vaporization enthalpy and vapor pressure of Δ<sup>8</sup>-THC is evaluated by correlation gas chromatography using a surrogate and compared to the experimental values evaluated for its Δ<sup>9</sup> isomer. Estimations using only group additivity, included in the Supporting Information, are provided for comparison. Agreement between estimates by synthetic analysis, correlation gas chromatography, and group additivity is quite good.</p>

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A series of cannabinoids including, cannabidiol, cannabigerol, cannabichromene, and Δ8- and Δ9-tetrahydrocannabinol are estimated using synthetic and retrosynthetic analysis, group additivity, and experiment

  • James S. Chickos

摘要

Synthetic and retrosynthetic analysis together group additivity and experiment have been used to estimate the vaporization enthalpies of a series of cannabinoids. The cannabinoids include Δ8-tetrahydrocannabinol (Δ8 -THC), Δ9-tetrahydrocannabinol (Δ9 -THC), cannabidiol (CBD), cannabigerol (CBG), cannabichromene (CBC), and four homologs of Δ9 -THC, CBD, CBG, and CBC: tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), and cannabigeroverin (CBGV), and cannabichromevarin (CBCV), respectively. Several new group properties have been derived from existing group values and also from the literature to complete previous estimations of both Δ9 -THC and Δ8 -THC reported earlier. The additional group values supplement those reported previously by Guthrie and Taylor. In addition, the vaporization enthalpy and vapor pressure of Δ8-THC is evaluated by correlation gas chromatography using a surrogate and compared to the experimental values evaluated for its Δ9 isomer. Estimations using only group additivity, included in the Supporting Information, are provided for comparison. Agreement between estimates by synthetic analysis, correlation gas chromatography, and group additivity is quite good.