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| == Pharmacology == | == Pharmacology == | ||
| Like Δ<sup>9</sup>-THC, 11-hydroxy-THC is a partial agonist at the ] ] with significantly higher ] (K<sub>i</sub> = 0.37 nM compared to Δ<sup>9</sup>-THC K<sub>i</sub> = 35 nM).<ref name="Zagzoog2022">{{cite journal | vauthors = Zagzoog A, Cabecinha A, Abramovici H, Laprairie RB | title = Modulation of type 1 cannabinoid receptor activity by cannabinoid by-products from ''Cannabis sativa'' and non-cannabis phytomolecules | journal = Frontiers in Pharmacology | volume = 13 | pages = 956030 | date = 26 August 2022 | pmid = 36091813 | doi = 10.3389/fphar.2022.956030 | pmc = 9458935 | doi-access = free }}</ref> With respect to ] inhibition at CB<sub>1</sub> it displays a similar efficacy to that of Δ<sup>9</sup>-THC (EC<sub>50</sub> = 11 nM vs. EC<sub>50</sub> = 5.2 nM, respectively), but a lower maximum response (E<sub>max</sub> = 28% vs. E<sub>max</sub> = 70%).<ref name="Zagzoog2022" /> | Like Δ<sup>9</sup>-THC, 11-hydroxy-THC is a partial agonist at the ] ] with significantly higher ] (K<sub>i</sub> = 0.37 nM compared to Δ<sup>9</sup>-THC K<sub>i</sub> = 35 nM).<ref name="Zagzoog2022">{{cite journal | vauthors = Zagzoog A, Cabecinha A, Abramovici H, Laprairie RB | title = Modulation of type 1 cannabinoid receptor activity by cannabinoid by-products from ''Cannabis sativa'' and non-cannabis phytomolecules | journal = Frontiers in Pharmacology | volume = 13 | pages = 956030 | date = 26 August 2022 | pmid = 36091813 | doi = 10.3389/fphar.2022.956030 | pmc = 9458935 | doi-access = free }}</ref> With respect to ] inhibition at CB<sub>1</sub> it displays a similar efficacy to that of Δ<sup>9</sup>-THC (EC<sub>50</sub> = 11 nM vs. EC<sub>50</sub> = 5.2 nM, respectively), but a lower maximum response (E<sub>max</sub> = 28% vs. E<sub>max</sub> = 70%).<ref name="Zagzoog2022" /> | ||
| == Research == | |||
| In an '']'' analysis by the ] on ] it was found that 11-OH-Δ<sup>9</sup>-THC had the 3rd highest ] inhibitor activity against ] out of all the cannabinoids tested within that study but not as high as the ] ] (56% 11-OH-Δ<sup>9</sup>-THC vs 100% GC376).<ref>{{cite journal | vauthors = Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H | title = 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 | journal = Molecules | volume = 27 | issue = 18 | page = 6127 | date = September 2022 | pmid = 36144858 | pmc = 9502466 | doi = 10.3390/molecules27186127 | doi-access = free }}</ref> | |||
| == See also == | == See also == | ||
Revision as of 20:55, 24 January 2024
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-Δ-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ-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
Like Δ-THC, 11-hydroxy-THC is a partial agonist at the cannabinoid receptor CB1 with significantly higher binding affinity (Ki = 0.37 nM compared to Δ-THC Ki = 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 (Emax = 28% vs. Emax = 70%).
See also
- 3'-Hydroxy-THC
- 7-Hydroxycannabidiol
- 8,11-Dihydroxytetrahydrocannabinol
- 11-OH-CBN
- Cannabis edible
- Delta-11-Tetrahydrocannabinol
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". 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.
- 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.
- ^ 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.
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