Chemistry:Isotetrahydrocannabinol

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Isotetrahydrocannabinol (iso-THC or Δ8-Isotetrahydrocannabinol) is a phytocannabinoid commonly found as a component in synthetic THC which has been made from acid-catalyzed cyclization of cannabidiol.[1] iso-THC can be described as the upper cyclization product of CBD, while THC is the lower cyclization product of CBD. Its pharmacology has not been studied, though it is commonly found in commercially marketed Δ8-THC products.[2][3][4][5]

Via a migration of the exocyclic double bond iso-THC can easily rearrange to delta-4(8)-iso-THC, which can also be found in Δ8 THC products.[6]

Iso-THC can be found as an impurity in pharmaceutical Dronabinol.[7][8]


See also

References

  1. ↑ "Acid-Catalyzed Conversion of Cannabidiol to Tetrahydrocannabinols: En Route to Demystifying Manufacturing Processes and Controlling the Reaction Outcomes" (in en). Cannabis and Cannabinoid Research 10 (3): 377–388. June 2025. doi:10.1089/can.2025.0015. ISSN 2578-5125. PMID 40250991. https://www.liebertpub.com/doi/10.1089/can.2025.0015. 
  2. ↑ "Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization". Journal of Natural Products 83 (10): 2894–2901. October 2020. doi:10.1021/acs.jnatprod.0c00436. PMID 32991167. 
  3. ↑ "Synthetic Strategies for Rare Cannabinoids Derived from Cannabis sativa". Journal of Natural Products 85 (6): 1555–1568. June 2022. doi:10.1021/acs.jnatprod.2c00155. PMID 35648593. 
  4. ↑ "Isolation and Characterization of Impurities in Commercially Marketed Δ8-THC Products". Journal of Natural Products 86 (4): 822–829. April 2023. doi:10.1021/acs.jnatprod.2c01008. PMID 36827690. 
  5. ↑ "Identification of hexahydrocannabinol (HHC), dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC) and hexahydrocannabiphorol (HHCP) in electronic cigarette cartridge products". Forensic Toxicology 42 (1): 71–81. June 2023. doi:10.1007/s11419-023-00667-9. PMID 37365398. 
  6. ↑ "Ultrafast, Selective, and Highly Sensitive Nonchromatographic Analysis of Fourteen Cannabinoids in Cannabis Extracts, Δ8-Tetrahydrocannabinol Synthetic Mixtures, and Edibles by Cyclic Ion Mobility Spectrometry-Mass Spectrometry". Analytical Chemistry 96 (25): 10170–10181. June 2024. doi:10.1021/acs.analchem.3c05879. PMID 38862388. 
  7. ↑ "Pharmacology Review: NDA 205525". U.S. Food and Drug Administration. 2016. https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/205525Orig1s000PharmR.pdf. 
  8. ↑ "Investigation of the Impurities in Dronabinol Samples by LC/MS". Cerilliant Corporation. https://www.cerilliant.com/shoponline/OpenDocument.aspx?DocumentID=38. 




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