Isotetrahydrocannabinol

Isotetrahydrocannabinol
Identifiers
	IUPAC name (1R,12R)-9-Methyl-5-pentyl-12-prop-1-en-2-yl-8-oxatricyclo[7.3.1.02,7]trideca-2,4,6-trien-3-ol;
PubChem CID	166057750;
Chemical and physical data
Formula	C21H30O2
Molar mass	314.469 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C=C(C)[C@@H]1CCC2(C)C[C@H]1c1c(cc(CCCCC)cc1O)O2;
	InChI InChI=1S/C21H30O2/c1-5-6-7-8-15-11-18(22)20-17-13-21(4,23-19(20)12-15)10-9-16(17)14(2)3/h11-12,16-17,22H,2,5-10,13H2,1,3-4H3/t16-,17?,21?/m0/s1; Key:NUXUDGMVYZUFNQ-BQJIDLTASA-N;

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]

References

^ Marzullo P, Foschi F, Coppini DA, Fanchini F, Magnani L, Rusconi S, et al. (October 2020). "Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization". Journal of Natural Products. 83 (10): 2894–2901. doi:10.1021/acs.jnatprod.0c00436. PMC 8011986. PMID 32991167.
^ Nguyen GN, Jordan EN, Kayser O (June 2022). "Synthetic Strategies for Rare Cannabinoids Derived from Cannabis sativa". Journal of Natural Products. 85 (6): 1555–1568. doi:10.1021/acs.jnatprod.2c00155. PMID 35648593. S2CID 249234673.
^ Radwan MM, Wanas AS, Gul W, Ibrahim EA, ElSohly MA (April 2023). "Isolation and Characterization of Impurities in Commercially Marketed Δ⁸-THC Products". Journal of Natural Products. 86 (4): 822–829. doi:10.1021/acs.jnatprod.2c01008. PMID 36827690. S2CID 257183893.
^ Tanaka R, Kikura-Hanajiri R (June 2023). "Identification of hexahydrocannabinol (HHC), dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC) and hexahydrocannabiphorol (HHCP) in electronic cigarette cartridge products". Forensic Toxicology. 42 (1): 71–81. doi:10.1007/s11419-023-00667-9. PMID 37365398. S2CID 259259903.

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[1] Marzullo P, Foschi F, Coppini DA, Fanchini F, Magnani L, Rusconi S, et al. (October 2020). "Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization". Journal of Natural Products. 83 (10): 2894–2901. doi:10.1021/acs.jnatprod.0c00436. PMC 8011986. PMID 32991167.

[2] Nguyen GN, Jordan EN, Kayser O (June 2022). "Synthetic Strategies for Rare Cannabinoids Derived from Cannabis sativa". Journal of Natural Products. 85 (6): 1555–1568. doi:10.1021/acs.jnatprod.2c00155. PMID 35648593. S2CID 249234673.

[3] Radwan MM, Wanas AS, Gul W, Ibrahim EA, ElSohly MA (April 2023). "Isolation and Characterization of Impurities in Commercially Marketed Δ⁸-THC Products". Journal of Natural Products. 86 (4): 822–829. doi:10.1021/acs.jnatprod.2c01008. PMID 36827690. S2CID 257183893.

[4] Tanaka R, Kikura-Hanajiri R (June 2023). "Identification of hexahydrocannabinol (HHC), dihydro-iso-tetrahydrocannabinol (dihydro-iso-THC) and hexahydrocannabiphorol (HHCP) in electronic cigarette cartridge products". Forensic Toxicology. 42 (1): 71–81. doi:10.1007/s11419-023-00667-9. PMID 37365398. S2CID 259259903.

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Identifiers


IUPAC name (1R,12R)-9-Methyl-5-pentyl-12-prop-1-en-2-yl-8-oxatricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-3-ol
PubChem CID	166057750
Chemical and physical data
Formula	C₂₁H₃₀O₂
Molar mass	314.469 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C=C(C)[C@@H]1CCC2(C)C[C@H]1c1c(cc(CCCCC)cc1O)O2
InChI InChI=1S/C21H30O2/c1-5-6-7-8-15-11-18(22)20-17-13-21(4,23-19(20)12-15)10-9-16(17)14(2)3/h11-12,16-17,22H,2,5-10,13H2,1,3-4H3/t16-,17?,21?/m0/s1 Key:NUXUDGMVYZUFNQ-BQJIDLTASA-N

Isotetrahydrocannabinol

See also

References