Isotetrahydrocannabinol Explained

Iupac Name:	(1R,12R)-9-Methyl-5-pentyl-12-prop-1-en-2-yl-8-oxatricyclo[7.3.1.0<sup>2,7</sup>]trideca-2,4,6-trien-3-ol
Width:	220px
Width2:	220px
Pubchem:	166057750
C:	21
H:	30
O:	2
Smiles:	C=C(C)[C@@H]1CCC2(C)C[C@H]1c1c(cc(CCCCC)cc1O)O2

Isotetrahydrocannabinol (iso-THC) is a phytocannabinoid similar in structure to cannabicitran which has been identified as a trace component of Cannabis, but is more commonly found as an impurity in synthetic THC which has been made from cannabidiol. iso-THC is present with other isomers with the double bond in a different position and the saturated dihydro derivative. 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 as a trace impurity in commercially marketed Δ⁸-THC products.^{[1] [2] [3] [4]}

See also

• Abeo-HHC acetate
• Cannabicyclol
• Cannabielsoin
• Cis-THC
• Exo-THC

Notes and References

1. Marzullo P, Foschi F, Coppini DA, Fanchini F, Magnani L, Rusconi S, Luzzani M, Passarella D . 6 . Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization . Journal of Natural Products . 83 . 10 . 2894–2901 . October 2020 . 10.1021/acs.jnatprod.0c00436 . 32991167 . 8011986 .
2. Nguyen GN, Jordan EN, Kayser O . Synthetic Strategies for Rare Cannabinoids Derived from Cannabis sativa . Journal of Natural Products . 85 . 6 . 1555–1568 . June 2022 . 10.1021/acs.jnatprod.2c00155 . 35648593 . 249234673 .
3. Radwan MM, Wanas AS, Gul W, Ibrahim EA, ElSohly MA . Isolation and Characterization of Impurities in Commercially Marketed Δ⁸-THC Products . Journal of Natural Products . 86 . 4 . 822–829 . April 2023 . 10.1021/acs.jnatprod.2c01008 . 36827690 . 257183893 .
4. Tanaka R, Kikura-Hanajiri R . Identification of hexahydrocannabinol (HHC), dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC) and hexahydrocannabiphorol (HHCP) in electronic cigarette cartridge products . Forensic Toxicology . June 2023 . 10.1007/s11419-023-00667-9 . 37365398 . 259259903 .