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11-Hydroxy-THC
Active metabolite of Δ9-THC
Active metabolite of Δ9-THC
| Field | Value | |
|---|---|---|
| Verifiedfields | changed | |
| Watchedfields | changed | |
| verifiedrevid | 477208799 | |
| IUPAC_name | (6*aR*,10*aR*)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6*a*,7,8,10*a*-tetrahydro-6*H*-benzo[*c*]chromen-1-ol | |
| image | 11-OH-THC.svg | |
| image_class | skin-invert-image | |
| width | 250px | |
| image2 | 11-Hydroxy-THC-3D-balls.png | |
| image_class2 | bg-transparent | |
| alt2 | 11-Hydroxy-THC molecule | |
| legal_UK | Class B | |
| routes_of_administration | ||
| excretion | ||
| CAS_number_Ref | ||
| CAS_number | 36557-05-8 | |
| UNII_Ref | ||
| UNII | 9VY04N5SLB | |
| ATC_prefix | None | |
| PubChem | 37482 | |
| KEGG | C22778 | |
| synonyms | 11-OH-Δ9-THC; 7-OH-Δ1-THC; 11-hydroxy-THC | |
| ChemSpiderID_Ref | ||
| ChemSpiderID | 34385 | |
| class | Cannabinoid | |
| <!--Chemical data--> | C | 21 |
| H | 30 | |
| O | 3 | |
| smiles | OC1=C2[C@]3([C@](C(C)(C)OC2=CC(CCCCC)=C1)(CCC(CO)=C3)[H])[H] | |
| StdInChI_Ref | ||
| StdInChI | 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 | |
| StdInChIKey_Ref | ||
| StdInChIKey | YCBKSSAWEUDACY-UHFFFAOYSA-N |
| elimination_half-life =
11-Hydroxy-Δ9-tetrahydrocannabinol (11-OH-Δ9-THC, alternatively numbered as 7-OH-Δ1-THC), usually referred to as 11-hydroxy-THC within cannabis culture, is the main active metabolite of tetrahydrocannabinol (THC), the major psychoactive substance in marijuana.
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 dehydrogenase and CYP2C9 enzymes to form 11-nor-9-carboxy-THC (THC-COOH), which is inactive at the CB1 receptors; in the liver, from where it is subsequently excreted through feces and urine. Both metabolites can be assayed in drug tests.
11-hydroxy-THC is formed after human consumption of THC containing products regardless of administration route, although levels of 11-hydroxy-THC are typically higher when cannabis products are eaten instead of inhaled.
Pharmacology
Like Δ9-THC, 11-hydroxy-THC is a partial agonist at the cannabinoid receptor CB1, but with significantly higher binding affinity (Ki = 0.37 nM compared to Δ9-THC Ki = 35 nM). With respect to cAMP inhibition at CB1 it displays a similar potency to that of Δ9-THC (EC50 = 11 nM vs. EC50 = 5.2 nM, respectively), but a lower maximum response, i.e., efficacy (Emax = 28% vs. Emax = 70%).
Research
In an in vitro analysis by the University of Rhode Island on cannabinoids it was found that 11-OH-Δ9-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% for 11-OH-Δ9-THC vs. 100% for GC376).
References
References
- (August 2007). "Bioanalytical procedures for determination of drugs of abuse in blood". Analytical and Bioanalytical Chemistry.
- (2005). "Cannabinoids".
- (February 2014). "Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review". Drug Metabolism Reviews.
- (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clinical Pharmacokinetics.
- (1992). "Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana". Journal of Analytical Toxicology.
- (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.
- (26 August 2022). "Modulation of type 1 cannabinoid receptor activity by cannabinoid by-products from ''Cannabis sativa'' and non-cannabis phytomolecules". Frontiers in Pharmacology.
- (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.
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