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Revision as of 19:17, 6 March 2023 by Gettinglit (talk | contribs) (Removed uncited marketing claims)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Chemical compound For the isomer of this chemical inherited from Δ-tetrahydrocannabinol, see 11-Hydroxy-Delta-8-THC. Pharmaceutical compound | |
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| Drug class | Cannabinoid |
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| ECHA InfoCard | 100.164.583  |
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| Formula | C21H30O3 |
| Molar mass | 330.468 g·mol |
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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 the dehydrogenase and CYP2C9 enzyme to form 11-nor-9-carboxy-THC (THC-COOH) which is inactive at the CB1 receptors; and further glucuronidated to form 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid glucuronide (delta-9-THC-COOH-glu) where it is excreted in both feces and urine. Both compounds, along with THC, can be assayed in drug tests.
11-hydroxy-THC can be formed after consumption of THC from inhalation (vaping, smoking) and oral (by mouth, edible, sublingual) use, although levels of 11-hydroxy-THC are typically higher when eaten compared to inhalation.
Pharmacology
In an analysis by the University of Rhode Island on cannabinoids it was found that 11-OH-D9-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-D9-THC) vs 100% GC376).
See also
Notes
References
- ^ 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.
- ^ Huestis MA (2005). "Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol". Handbook of Experimental Pharmacology. 168 (168): 657–690. doi:10.1007/3-540-26573-2_23. ISBN 3-540-22565-X. PMID 16596792.
- 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.
- Grotenhermen F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clinical Pharmacokinetics. 42 (4): 327–360. doi:10.2165/00003088-200342040-00003. PMID 12648025. S2CID 25623600.
- 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.
- 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.
- Liu, Chang; Puopolo, Tess; Li, Huifang; Cai, Ang; Seeram, Navindra P.; Ma, Hang (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.
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