11-Hydroxy-THC
Active metabolite of Δ9-THC
From Wikipedia, the free encyclopedia
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.[1][2]
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| Other names | 11-OH-Δ9-THC; 7-OH-Δ1-THC; 11-hydroxy-THC |
| Drug class | Cannabinoid |
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| ECHA InfoCard | 100.164.583 |
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| Formula | C21H30O3 |
| Molar mass | 330.468 g·mol−1 |
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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[which?] 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.[4] Both metabolites can be assayed in drug tests.[1]
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.[5][6]
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).[7] 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%).[7]
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).[8]