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 Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC' ...

(THC), which is formed in the body after THC is consumed. After

cannabis consumption Cannabis consumption refers to the variety of ways cannabis is consumed, among which inhalation (smoking and vaporizing) and ingestion are most common. All consumption methods involve heating the plant's THCA to decarboxylate it into THC, eith ...

, THC is

metabolized Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...

inside the body by cytochrome P450 enzymes such as

CYP2C9 Cytochrome P450 family 2 subfamily C member 9 (abbreviated CYP2C9) is an enzyme protein. The enzyme is involved in metabolism, by oxidation, of both xenobiotics, including drugs, and endogenous compounds, including fatty acids. In humans, the pro ...

and CYP3A4 into 11-hydroxy-THC and then further metabolized by the dehydrogenase and

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 The 3C-like protease (3CLpro) or main protease (Mpro), formally known as C30 endopeptidase or 3-chymotrypsin-like protease, is the main protease found in coronaviruses. It cleaves the coronavirus polyprotein at eleven conserved sites. It is a ...

inhibitor activity against

COVID-19 Coronavirus disease 2019 (COVID-19) is a contagious disease caused by a virus, the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The first known case was identified in Wuhan, China, in December 2019. The disease quick ...

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). The pharmacokinetic equivalency was studied in 2015 comparing Delta-9-THC with 11-Hydroxy-Δ9-tetrahydrocannabinol and found "The base pharmacokinetic equivalency ratio is 1 to 5.71. This means that one milligram of THC in edible form, is equivalent to 5.71 milligrams of THC in smokable form."

References

{{DEFAULTSORT:Hydroxy-THC, 11- Cannabinoids Benzochromenes Primary alcohols Phenols Prodrugs

Pharmacology

See also

References