Cannabidiol (CBD) Isomerization to Psychoactive Cannabinoids

With Battery acid

1. 1 g of CBD was added to 35 ml of 95% ethanol in a 50 ml Round Bottom Flask (RBF).

2. Placed in a hot water bath at 70°C.3. Once the CBD was dissolved, 4 drops of 35% sulfuric acid were added to acidify the solution, pH<3.

4. The mixture was allowed to reflux for 24 h in the water bath of 70°C.

5. Once complete, 5 drops of 10M NaOH was used to basify the solution until the pH was greater than 10, which removes the sulfuric acid as sodium sulfate.

6. The reaction was then filtered to remove the sodium sulfate, which allowed for just the cannabinoids to be in the remaining ethanol solution.

7. The 0-h sample extraction resulted in only CBD being found at 2.80 min, which agrees with the reference samples of 2.80 min. After 1-h, the CBD peak was reduced, but still was the main peak present. However, other impurities began to increase after 24 h such as at 2.18 min and 3.40 min, which were found to be 8-OH-iso-HHC and 9α-OH-HHC. Additionally, the D 9-THC and D 8-THC doublet was found at 4.10 min and 4.22 min. Another peak at 3.77 min was found to be an isomerization peak of D 9-THC and is thought to be D 11-THC or D 7-THC. This method did not isomerize all the CBD even at 24 h. However, the CBD peak was no longer the most prominent peak in the sample. The largest peak was found to be the 3.38 peaks, which was 9α-OH-HHC.

With Muriatic acid

1. 1 g of CBD was added to 35 ml of 95% ethanol in a 50 ml RBF.

2. Placed in a hot water bath at 70°C.

3. Once the CBD was dissolved, 47.3 ml of 37% hydrochloric acid were added to the solution, making it a final concentration of 0.05% HCl with a pH of less than 5.

4. The mixture was allowed to reflux for 24 h in the water bath of 70°C.

5. The 0-h sample extraction resulted in only CBD being found at 2.80 min, which agrees with the reference samples of 2.80 min. After 1-h, the CBD peak was reduced, but still was the main peak present. However, other impurities began to increase after 24 h such as at 2.18 min and 3.40 min, which were found to be 8-OH-iso- HHC and 9α-OH-HHC. Additionally, the D 9-THC and D 8-THC doublet was found at 4.10 min and 4.22 min. Another peak at 3.77 min was found to be an isomerization peak of D 9-THC and is thought to be D 11-THC or D 7-THC. Fragmentation was conducted and found that it has the same fragmentation and ratios as D 9-THC and D 8-THC, confirming that it is an isomer of D 9-THC and D 8-THC. This method did not isomerize all the CBD even at 24 h. However, the CBD peak was no longer the most prominent peak in the sample. The largest peak was found to be the 3.38 peaks, which was 9α-OH-HHC.

With Glacial Acetic Acid

1. 1 g of CBD was added to 35 ml of 95% ethanol in a 50 ml RBF.

2. Placed in a hot water bath at 70°C.

3. Once the CBD was dissolved, 1.909 ml of 99% glacial acetic acid were added to the solution, making it a final concentration of 5.2% acetic acid.

4. The mixture was allowed to reflux for 24 h in the water bath of 70°C.

5. The 0-h sample extraction resulted in only CBD being found at 2.80 min, which agrees with the reference samples of 2.80. After 1-h, changes of CBD isomerization were only found as an increase in the peak at 3.77, which is thought to be D 11-THC or D 7-THC. After 4h, a noticeable peak of increasing D 9-THC was found to increase. At 24 h, the reaction was analyzed and found that 11-5 00 -dihydroxy-CBD, 8-OH-iso-HHC, CBD, 10-methoxy-THC, and D 9-THC were found at 1.96 min, 2.22 min, 2.80 min, 3.50 min, and 4.11 min, respectively. The compound at 3.77 min was found in these spectra and was the most abundant after 24 h.