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 In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

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, e ...

, 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 Cytochromes P450 (CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are ...

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 prote ...

and

CYP3A4 Cytochrome P450 3A4 (abbreviated CYP3A4) () is an important enzyme in the body, mainly found in the liver and in the intestine. It oxidizes small foreign organic molecules (xenobiotics), such as toxins or drugs, so that they can be removed from t ...

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

dehydrogenase A dehydrogenase is an enzyme belonging to the group of oxidoreductases that oxidizes a substrate by reducing an electron acceptor, usually NAD+/NADP+ or a flavin coenzyme such as FAD or FMN. Like all catalysts, they catalyze reverse as well as f ...

and

enzyme to form 11-nor-9-carboxy-THC (THC-COOH) which is inactive at the CB1 receptors; and further

glucuronidated Glucuronidation is often involved in drug metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosid ...

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 The University of Rhode Island (URI) is a public land-grant research university with its main campus in Kingston, Rhode Island, United States. It is the flagship public research as well as the land-grant university of the state of Rhode Island ...

cannabinoids Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

it was found that 11-OH-D9-THC had the 3rd highest 3C-like protease 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 COVID-19 pandemic in Hubei, identified in Wuhan, China, in December ...

out of all the cannabinoids tested within that study but not as high as the

antiviral drug Antiviral drugs are a class of medication used for treating viral infections. Most antivirals target specific viruses, while a broad-spectrum antiviral is effective against a wide range of viruses. Unlike most antibiotics, antiviral drugs do n ...

GC376 GC376 is a broad-spectrum antiviral medication under development by the biopharmaceutical company Anivive Lifesciences for therapeutic uses in humans and animals. Anivive licensed the exclusive worldwide patent rights to GC376 from Kansas State ...

(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