Cannabitriol

Cannabitriol
Clinical data
Other names	(+)-CBT, (S,S)-9,10-Dihydroxy-Δ6a(10a)-THC
Identifiers
	IUPAC name (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	156460;
ChemSpider	137777;
UNII	FV3E92D97V;
CompTox Dashboard (EPA)	DTXSID80911448 ;
Chemical and physical data
Formula	C21H30O4
Molar mass	346.467 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=CC(=C2C(=C1)OC(C3=C2[C@@H]([C@@](CC3)(C)O)O)(C)C)O;
	InChI 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) is a phytocannabinoid first isolated in 1966,^[1]^[2]^[3] an oxidation product of tetrahydrocannabinol (THC) 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]

References

^ Obata Y, Ishikawa Y (June 1966). "Studies on the constituents of hemp plant (Cannabis sativa L.) Part III. Isolation of a gibbs-positive compound from Japanese hemp". Agricultural and Biological Chemistry. 30 (6): 619–620. doi:10.1080/00021369.1966.10858651.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

This cannabinoid related article is a stub. You can help Wikipedia by expanding it.

Clinical data

Other names	(+)-CBT, (S,S)-9,10-Dihydroxy-Δ^6a(10a)-THC
Identifiers
IUPAC name (9S,10S)-6,6,9-trimethyl-3-pentyl-8,10-dihydro-7H-benzo[c]chromene-1,9,10-triol
CAS Number	74184-29-5^Y 11003-36-4 (racemic)
PubChem CID	156460
ChemSpider	137777
UNII	FV3E92D97V
CompTox Dashboard (EPA)	DTXSID80911448
Chemical and physical data
Formula	C₂₁H₃₀O₄
Molar mass	346.467 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC1=CC(=C2C(=C1)OC(C3=C2[C@@H]([C@@](CC3)(C)O)O)(C)C)O
InChI 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