| Verifiedfields: | changed |
| Watchedfields: | changed |
| Verifiedrevid: | 477208799 |
| Iupac Name: | (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzo[''c'']chromen-1-ol |
| Width: | 250px |
| Alt2: | 11-Hydroxy-THC molecule |
| Legal Uk: | Class B |
| Cas Number: | 36557-05-8 |
| Unii: | 9VY04N5SLB |
| Pubchem: | 37482 |
| Kegg: | C22778 |
| Chemspiderid: | 34385 |
| Class: | Cannabinoid |
| C: | 21 |
| H: | 30 |
| O: | 3 |
| Smiles: | Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC |
| 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: | YCBKSSAWEUDACY-UHFFFAOYSA-N |
11-Hydroxy-Δ9-tetrahydrocannabinol (11-OH-Δ9-THC, alternatively numbered as 7-OH-Δ1-THC), usually referred to as 11-hydroxy-THC is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after Δ9-THC is consumed.[1] [2]
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;[2] and further glucuronidated to form 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ9-THC-COOH-glu)[3] in the liver, from where it is subsequently excreted through feces and urine (via bile from the liver).[4] Both metabolites, along with THC, can be assayed in drug tests.[1]
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.[5] [6]
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).[7] With respect to cAMP inhibition at CB1 it displays a similar efficacy to that of Δ9-THC (EC50 = 11 nM vs. EC50 = 5.2 nM, respectively), but a lower maximum response (Emax = 28% vs. Emax = 70%).
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).[8]