Cannabisol

Cannabisol
Identifiers
	IUPAC name (6aR,10aR)-2-[[(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-2-yl]methyl]-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol;
CAS Number	1384106-31-3;
PubChem CID	102487751;
CompTox Dashboard (EPA)	DTXSID701107446 ;
Chemical and physical data
Formula	C43H60O4
Molar mass	640.949 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1CC4=C(C5=C(C=C4CCCCC)OC([C@H]6[C@H]5C=C(CC6)C)(C)C)O)O;
	InChI InChI=1S/C43H60O4/c1-9-11-13-15-28-23-36-38(32-21-26(3)17-19-34(32)42(5,6)46-36)40(44)30(28)25-31-29(16-14-12-10-2)24-37-39(41(31)45)33-22-27(4)18-20-35(33)43(7,8)47-37/h21-24,32-35,44-45H,9-20,25H2,1-8H3/t32-,33-,34-,35-/m1/s1; Key:PDADLCKRVIFEGH-BAQBVXSRSA-N;

Cannabisol is a phytocannabinoid first isolated from Cannabis sativa in 2012, which is a dimer of THC found in trace amounts in cannabis plant material. Its bioactivity has not yet been studied, but similar dimeric forms of cannabidiol (known as cannabitwinol) and cannabigerol (known as cannabizetol) have also been reported more recently, and found to have TRP channel modulatory and antiinflammatory actions respectively.^[1]^[2]^[3]

References

^ Zulfiqar F, Ross SA, Slade D, Ahmed SA, Radwan MM, Ali Z, et al. (July 2012). "Cannabisol, a novel Δ⁹-THC dimer possessing a unique methylene bridge, isolated from Cannabis sativa". Tetrahedron Letters. 53 (28): 3560–3562. doi:10.1016/j.tetlet.2012.04.139. PMC 5045039. PMID 27695140.
^ Chianese G, Lopatriello A, Schiano-Moriello A, Caprioglio D, Mattoteia D, Benetti E, et al. (September 2020). "Cannabitwinol, a Dimeric Phytocannabinoid from Hemp, Cannabis sativa L., Is a Selective Thermo-TRP Modulator". Journal of Natural Products. 83 (9): 2727–2736. Bibcode:2020JNAtP..83.2727C. doi:10.1021/acs.jnatprod.0c00668. PMID 32880179.
^ Pozzi L, Gotti A, Fumagalli M, Citarella A, Fasano V, Paladino G, et al. (September 2025). "Cannabizetol, a Novel Cannabinoid: Chemical Synthesis, Anti-inflammatory Activity and Extraction from Cannabis sativa L". Journal of Natural Products acs.jnatprod.5c00826. doi:10.1021/acs.jnatprod.5c00826. PMC 12560071. PMID 40994228.

[1] Zulfiqar F, Ross SA, Slade D, Ahmed SA, Radwan MM, Ali Z, et al. (July 2012). "Cannabisol, a novel Δ⁹-THC dimer possessing a unique methylene bridge, isolated from Cannabis sativa". Tetrahedron Letters. 53 (28): 3560–3562. doi:10.1016/j.tetlet.2012.04.139. PMC 5045039. PMID 27695140.

[2] Chianese G, Lopatriello A, Schiano-Moriello A, Caprioglio D, Mattoteia D, Benetti E, et al. (September 2020). "Cannabitwinol, a Dimeric Phytocannabinoid from Hemp, Cannabis sativa L., Is a Selective Thermo-TRP Modulator". Journal of Natural Products. 83 (9): 2727–2736. Bibcode:2020JNAtP..83.2727C. doi:10.1021/acs.jnatprod.0c00668. PMID 32880179.

[3] Pozzi L, Gotti A, Fumagalli M, Citarella A, Fasano V, Paladino G, et al. (September 2025). "Cannabizetol, a Novel Cannabinoid: Chemical Synthesis, Anti-inflammatory Activity and Extraction from Cannabis sativa L". Journal of Natural Products acs.jnatprod.5c00826. doi:10.1021/acs.jnatprod.5c00826. PMC 12560071. PMID 40994228.

[1]

[2]

[3]

See also

References