Draft:Conversion of CBD to THC

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Cannabidiol (CBD) can be chemically converted into tetrahydrocannabinol (THC) via a ring-closing reaction. This cyclization can be acid-catalyzed or brought about by heating.

Known methods[edit]

At least different three methods, that are independent of each other, have been utilized to convert CBD to THC.

  • Despite the CBD and THC having the same molecular weight, multiple analytical methods are able to differentiate them.[1]
  • "on the recovery of both THC (86.7−90.0%) and CBD (92.3−95.6%). The slightly lower recovery of THC can be explained by the fact that THC is less polar than CBD and more likely to remain in the nonpolar sunflower oil."[1]

By heat[edit]

CBD heated to 175,[2] or 250–300 °C may partially be converted into THC.[3]

  • Heat is required to decarboxylate THCA to psychoactive cannabinoid THC. Likewise, CBDA turns into CBD.
  • From hemp plant material in an oven, cannabinoid concentration plots (time/temp) show THC:[4]
  • STP 0 minutes 0.20mg/g
  • 140-160C 20 minutes 0.27mg/g
  • 140-160C 60 minutes 0.05-0.15mg/g
  • 120C 45 minutes 0.27mg/g
  • 120C 90 minutes 0.20mg/g
  • 100C 90 minutes 0.25mg/g
  • 80C 120 minutes 0.24mg/g

Multiple oxidation products begin to form with degradation (the loss is greatly reduced in the absence of oxygen).

  • "the boiling point for THC has been determined at 157 °C, and the boiling point range for CBD sits between 160 and 180 °C."[4]

With acid[edit]

Mechanism of the acid catalyzed conversion of CBD into THC

CBD converts to various isomers of THC with catalysts in acidic environments.[5][6]

  • add protons until the CBD sterically-hindered alcohol functional group becomes the ether heterocyclic hexane in THC re:Figure 4.(b)[7]

With zeolite[edit]

"Zeolites selected from the group consisting of analcime, chabazite, clinoptilolite, erionite, mordenite, phillipsite, and ferrierite."[8]

In vivo[edit]

There is a debated hypothesis that oral CBD is converted into THC under acidic conditions in the stomach and then absorbed into the blood stream. However, neither THC nor any of its active metabolites have been detected in blood in animals or humans after ingesting CBD.[6] There is no direct evidence of the conversion of CBD to THC in the human gut; both CBD and THC are excreted unchanged within feces.[5]

"An important consideration for the cannabinoid analysis is that cannabinoids from plants are effectively in a “prodrug” form, existing as cannabinolic acids that must be decarboxylated to their respective cannabinol form to have pharmacological effects.2 This decarboxylation, for example, occurs while smoking; however, upon oral consumption, no CBDA or THCA present is converted to CBD or THC by enzymatic or other processes.37,38 If the production and processing of CBD oils does not remove all THCA and CBDA, some THCA and CBDA might still be present in the final CBD oil products."[1]

References[edit]

  1. ^ a b c Huang, S., Claassen, F. W., Van Beek, T. A., Chen, B., Zeng, J., Zuilhof, H., Salentijn, G. Ij. (2 March 2021). "Rapid Distinction and Semiquantitative Analysis of THC and CBD by Silver-Impregnated Paper Spray Mass Spectrometry". Analytical Chemistry. 93 (8): 3794–3802. doi:10.1021/acs.analchem.0c04270. ISSN 1520-6882 0003-2700, 1520-6882. Retrieved 17 May 2024. {{cite journal}}: Check |issn= value (help)
  2. ^ Daniels, R; Yassin, OA; Toribio, JM; Gascón, JA; Sotzing, G. doi:10.1089/can.2022.0235. PMID 36516105. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  3. ^ Czégény Z, Nagy G, Babinszki B, Bajtel Á, Sebestyén Z, Kiss T, et al. (April 2021). "CBD, a precursor of THC in e-cigarettes". Scientific Reports. 11 (1): 8951. Bibcode:2021NatSR..11.8951C. doi:10.1038/s41598-021-88389-z. PMC 8076212. PMID 33903673.
  4. ^ a b Moreno, T., Dyer, P., Tallon, S. (18 November 2020). "Cannabinoid Decarboxylation: A Comparative Kinetic Study". Industrial & Engineering Chemistry Research. 59 (46): 20307–20315. doi:10.1021/acs.iecr.0c03791. ISSN 1520-5045 0888-5885, 1520-5045. Retrieved 17 May 2024. {{cite journal}}: Check |issn= value (help)
  5. ^ a b <Nelson, K. M., Bisson, J., Singh, G., Graham, J. G., Chen, S.-N., Friesen, J. B., Dahlin, J. L., Niemitz, M., Walters, M. A., Pauli, G. F. (12 November 2020). "The Essential Medicinal Chemistry of Cannabidiol (CBD)". Journal of Medicinal Chemistry. 63 (21): 12137–12155. doi:10.1021/acs.jmedchem.0c00724. ISSN 1520-4804 0022-2623, 1520-4804. Retrieved 17 May 2024. {{cite journal}}: Check |issn= value (help)
  6. ^ a b <Golombek P, Müller M, Barthlott I, Sproll C, Lachenmeier DW (June 2020). "Conversion of Cannabidiol (CBD) into Psychotropic Cannabinoids Including Tetrahydrocannabinol (THC): A Controversy in the Scientific Literature". Toxics. 8 (2): 41. doi:10.3390/toxics8020041. PMC 7357058. PMID 32503116.
  7. ^ Peng, H., Shahidi, F. (17 February 2021). "Cannabis and Cannabis Edibles: A Review". Journal of Agricultural and Food Chemistry. 69 (6): 1751–1774. doi:10.1021/acs.jafc.0c07472. ISSN 1520-5118 0021-8561, 1520-5118. Retrieved 17 May 2024. {{cite journal}}: Check |issn= value (help)
  8. ^ US 11352337B1, Gindelberger D, "Zeolite catalyst and method for preparation of aromatic tricyclic pyrans", issued 7 June 2022, assigned to Acid Neutral Alkaline Laboratory.