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https://future4200.com/t/cbd-isomeri...-thc/75212/632
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EXAMPLE I A quantity of dry hemp chaff was placed in a bag together with an operative ozonegenerating machine (BESTEK 03 ozone generator/air sterilizer model: BTAS807) for approximately 1.5 hours. A sample of each of the treated and the untreated hemp was pulverized and prepared for smoking using standard methods known in the art. The sample was smoked by 15 professional smokers trained to recognise a psychoactive effect prior to the experiment. 14 out of 15 panellists confirmed a psychoactive effect of the treated sample but not the untreated sample. The sample is further subjected to NMR/IR spectroscopy and presence of A9-THC and A8-THC, as well as other ozonated cannabinoid products confirmed.
EXAMPLE II
Ozonation of hemp was carried out as per Example I above. The ozonated product was sampled by a subject suffering from chronic pain and anxiety. The product was firstly smoked by the subject. The subject confirmed amelioration of symptoms, in particular lessening of pain. On a separate occasion, the subject mixed the product with edible oil and ingested the product. The subject again confirmed amelioration of symptoms, but more long-lasting than when smoked.
EXAMPLE III
Ozone was produced from oxygen under electric discharge conditions. Before being fed into the ozone generator, oxygen was dried with Mg(CIO4)2. The solvent was CCI4 (reagent grade). Prior to performing the reaction, substrate (hempseed oil) was treated with an ozone-oxygen mixture (~10% O3) for 30 min for decomposing the possible active impurities, held over calcium chloride, and distilled. Ozonation was carried out in a temperature-controlled bubbler under steady-state conditions. The reaction was performed in the temperature-controlled sample cell of a spectrophotometer. An ozone-oxygen mixture was passed through the sample cell with a substrate solution until the necessary O3 concentration in the solution (1.7 χ 10-5 to 6.8 χ 10-4 mol/l) was reached. The blank in the reference cell was a solution containing the same substrate concentration. The substrate and ozone concentrations in the sample cell were chosen so that the substrate was at least in 100-fold excess over ozone. After the necessary O3 concentration was reached, the sample cell was sealed hermetically and the ozone consumption rate in the cell was monitored spectrophotometrically. Using this procedure, we determined the monomolecular ozone disappearance rate constant (kmono)· From the dependence of kmono on the substrate concentration, it is possible to determine the stoichiometry of the reaction and the ozonation rate constant at the given temperature.
EXAMPLE IV
Conversion of CBD to A8-THC. CBD (300 mg) was added to dried p-toluenesulfonic acid (30 mg) in toluene (15 ml), under O3 atmosphere. In this example, the mixture was refluxed (under O3) for 1 hour, although other time periods may also be used, as discussed below. It was then diluted with ether (20 ml) and poured into cold water. The upper layer was separated, washed with aqueous 5% NaHCO3, then with water, dried over MgSO4 and evaporated. The viscous oil showed mainly one spot on TLC (using 20% ether in petroleum ether as eluent). HPLC, on the crude oil, showed the presence of 87% A8-THC. The oil was chromatographed on a silica gel column (6 g). Elution with 5 to 10% ether in petroleum ether gave a fraction (244 mg, 81%) of A8-THC 98.8% pure. When the reaction was carried out using various reflux times showed the presence of 79.37% A8-THC (15 minutes), 81.9% Δ8-THC (30 minutes) and 84.7% A8-THC (2 hours).
EXAMPLE V
Conversion of CBD to A9-THC. BF3Et2O (50 ul) was added, under ozone atmosphere, to ice cold solution of CBD (300 mg) in dry methylene chloride (15 ml). The solution was stirred at 0° C for 1 hour. Saturated aqueous solution of NaHCO3 (2 ml) was added until the red colour faded. The organic layer was removed, washed with water, dried over MgSO4 and evaporated. The composition of the oil obtained (determined by HPLC): trans- A8-isoTHC 27%, A9-THC 69.7%. The oil was chromatographed on silica gel column (20 g) and eluted with petroleum ether followed by graded mixtures, up to 2:98 of ether in petroleum ether.
The first fraction eluted was the A8-isoTHC (30 mg, 9.5%) followed by a mixture of Δ8-ίεο THC and A9-THC (100 mg). The last compound to be eluted was the A9-THC (172 mg, 57%). The purity of A9-THC (as determined by HPLC) Was 98.9%. It is of note that when the reaction was carried in the presence of MgSO4 (120 mg), the composition of the oil obtained (determined by FIPLC) was: trans- A8isoTHC 21.15%, A9-THC 56.7%.