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11-Hydroxy-THC

Clinical data
Drug class	Cannabinoid
Legal status
Legal status	UK: Class B
Identifiers
IUPAC name (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzochromen-1-ol
CAS Number	36557-05-8
PubChem CID	37482
ChemSpider	34385
UNII	9VY04N5SLB
KEGG	C22778
CompTox Dashboard (EPA)	DTXSID50190061
ECHA InfoCard	100.164.583
Chemical and physical data
Formula	C21H30O3
Molar mass	330.468 g·mol
3D model (JSmol)	Interactive image
SMILES Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC
InChI InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3 Key:YCBKSSAWEUDACY-UHFFFAOYSA-N
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11-Hydroxy-Δ-tetrahydrocannabinol (11-OH-Δ-THC, alternatively numbered as 7-OH-Δ-THC), usually referred to as 11-hydroxy-THC is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after Δ-THC is consumed.

After cannabis consumption, THC is metabolized inside the body by cytochrome P450 enzymes such as CYP2C9 and CYP3A4 into 11-hydroxy-THC and then further metabolized by cytochrome enzymes to form 11-nor-9-carboxy-THC which is inactive at the CB₁ receptors; and further glucuronidated to form 11-nor-Δ-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ-THC-COOH-glu) in the liver, from where it is subsequently excreted through feces and urine (via bile from the liver). Both metabolites, along with THC, can be assayed in blood drug tests.

11-hydroxy-THC can be formed after consumption of cannabis from inhalation (vaping and smoking) and oral (swallowed or sublingual) use, although levels of 11-hydroxy-THC are typically higher when oral forms of the drug are used.

Pharmacology

Like Δ-THC, 11-hydroxy-THC is a partial agonist at the cannabinoid receptor CB₁, but with significantly higher binding affinity (K_i = 0.37 nM compared to Δ-THC K_i = 35 nM). With respect to cAMP inhibition at CB₁ it displays a similar efficacy to that of Δ-THC (EC₅₀ = 11 nM vs. EC₅₀ = 5.2 nM, respectively), but a lower maximum response (E_max = 28% vs. E_max = 70%).

Research

In an in vitro analysis by the University of Rhode Island on cannabinoids it was found that 11-OH-Δ-THC had the 3rd highest 3C-like protease inhibitor activity against COVID-19 out of all the cannabinoids tested within that study but not as high as the antiviral drug GC376 (56% 11-OH-Δ-THC vs 100% GC376).

See also

• 11-Hydroxy-Delta-8-THC
• 11-Hydroxyhexahydrocannabinol
• 3'-Hydroxy-THC
• 7-Hydroxycannabidiol
• 8,11-Dihydroxytetrahydrocannabinol
• 11-OH-CBN
• Cannabis edible
• Delta-11-Tetrahydrocannabinol

References

1. ^ Kraemer T, Paul LD (August 2007). "Bioanalytical procedures for determination of drugs of abuse in blood". Analytical and Bioanalytical Chemistry. 388 (7): 1415–1435. doi:10.1007/s00216-007-1271-6. PMID 17468860. S2CID 32917584.
2. ^ Huestis MA (2005). "Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol". Cannabinoids. Handbook of Experimental Pharmacology. Vol. 168. pp. 657–690. doi:10.1007/3-540-26573-2_23. ISBN 3-540-22565-X. PMID 16596792.
3. Stout SM, Cimino NM (February 2014). "Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review". Drug Metabolism Reviews. 46 (1): 86–95. doi:10.3109/03602532.2013.849268. PMID 24160757. S2CID 29133059.
4. Grotenhermen F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clinical Pharmacokinetics. 42 (4): 327–360. doi:10.2165/00003088-200342040-00003. PMID 12648025. S2CID 25623600.
5. Huestis MA, Henningfield JE, Cone EJ (1992). "Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana". Journal of Analytical Toxicology. 16 (5): 276–282. doi:10.1093/jat/16.5.276. PMID 1338215.
6. Karschner EL, Schwilke EW, Lowe RH, Darwin WD, Herning RI, Cadet JL, Huestis MA (October 2009). "Implications of plasma Delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers". Journal of Analytical Toxicology. 33 (8): 469–477. doi:10.1093/jat/33.8.469. PMC 3159863. PMID 19874654.
7. ^ Zagzoog A, Cabecinha A, Abramovici H, Laprairie RB (26 August 2022). "Modulation of type 1 cannabinoid receptor activity by cannabinoid by-products from Cannabis sativa and non-cannabis phytomolecules". Frontiers in Pharmacology. 13: 956030. doi:10.3389/fphar.2022.956030. PMC 9458935. PMID 36091813.
8. Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H (September 2022). "Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity". Molecules. 27 (18): 6127. doi:10.3390/molecules27186127. PMC 9502466. PMID 36144858.

• Cannabinoids
• Benzochromenes
• Primary alcohols
• Phenols