Cannabitriol
Identifiers
  • (9S,10S)-6,6,9-trimethyl-3-pentyl-8,10-dihydro-7H-benzo[c]chromene-1,9,10-triol
CAS Number
  • 74184-29-5
    11003-36-4 (racemic)
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H30O4
Molar mass346.467 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C2C(=C1)OC(C3=C2[C@@H]([C@@](CC3)(C)O)O)(C)C)O
  • InChI=1S/C21H30O4/c1-5-6-7-8-13-11-15(22)18-16(12-13)25-20(2,3)14-9-10-21(4,24)19(23)17(14)18/h11-12,19,22-24H,5-10H2,1-4H3/t19-,21-/m0/s1
  • Key:ZLYNXDIDWUWASO-FPOVZHCZSA-N

Cannabitriol ((+)-CBT, (S,S)-9,10-Dihydroxy-Δ6a(10a)-THC) is a phytocannabinoid first isolated in 1966,[1][2][3] an oxidation product of tetrahydrocannabinol which has been identified both as a trace component of cannabis and as a metabolite in cannabis users.[4] Its pharmacology has been little studied, though it has been found to act as an antiestrogen and aromatase inhibitor.[5][6]

See also

References

  1. ^ Obata Y, Ishikawa Y. Studies on the Constituents of Hemp Plant (Cannabis sativa L.), Agricultural and Biological Chemistry 1966; 30(6): 619–620. doi:10.1080/00021369.1966.10858651
  2. ^ Chan WR, Magnus KE, Watson HA (March 1976). "The structure of cannabitriol". Experientia. 32 (3): 283–4. doi:10.1007/BF01940792. PMID 1253891. S2CID 2679030.
  3. ^ Elsohly MA, El-Feraly FS, Turner CE (1977). "Isolation and characterization of (+)-cannabitriol and (-)-10-ethoxy-9-hydroxy-delta 6a[10a]-tetrahydrocannabinol: two new cannabinoids from Cannabis sativa L. extract". Lloydia. 40 (3): 275–80. PMID 895385.
  4. ^ White RM (January 2018). "Instability and poor recovery of cannabinoids in urine, oral fluid, and hair". Forensic Science Review. 30 (1): 33–49. PMID 29273570.
  5. ^ Baroi S, Saha A, Bachar R, Bachar SC (June 2020). "Cannabinoid as Potential Aromatase Inhibitor through Molecular Modeling and Screening for Anti-Cancer Activity". Dhaka University Journal of Pharmaceutical Sciences. 19 (1): 47–58. doi:10.3329/dujps.v19i1.47818. S2CID 225712476.
  6. ^ Kikiowo B, Ogunleye AJ, Iwaloye O, Ijatuyi TT, Adelakun NS, Alashe WO (2021). "Induced Fit Docking and Automated QSAR Studies Reveal the ER-α Inhibitory Activity of Cannabis sativa in Breast Cancer". Recent Patents on Anti-Cancer Drug Discovery. 16 (2): 273–284. doi:10.2174/1574892816666210201115359. PMID 33563181. S2CID 231865568.