11-OH-THC, 10-OH-THC and THC-COOH, THC metabolites and their legal status

With the fanfare surrounding the arrival of the HHC metabolite, 10-OH-HHC, and its growing notoriety, we wanted to take a closer look at the THC metabolites. These are called 11-OH-THC, 10-OH-THC, and THC-COOH.

This article explains what a metabolite is, what the metabolites of THC are, what their effects are and their legal status.

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What is a metabolite?

The term metabolite refers to metabolic derivatives. These are by-products created by the body when it assimilates a molecule.

In simple terms, when you consume THC, HHC, or CBD, the molecule enters your body and travels through your bloodstream. It is transported to the liver, which processes it so that it can be more easily eliminated from the body. In doing so, the molecule undergoes chemical changes. This is when 10-OH-HHC and 8-OH-HHC are formed for HHC, and 11-OH-THC, 10-OH-THC, and THC-COOH for THC.

But cannabinoids aren't the only molecules that give rise to other molecules when processed by the body. This is true of all active molecules, such as alcohol, which is converted into acetic acid, aspirin into salicylic acid, and all the active molecules found in food (lipids, carbohydrates, etc.) that are transformed into fatty acids, glucose, amino acids, and so on.

What are the metabolites of THC?

The three metabolites already mentioned, 11-OH-THC, 10-OH-THC and THC-COOH, are the three main metabolites of THC.

11-OH-THC and 10-OH-THC are quite similar to 8-oh-hhc and 10-oh-hhc in terms of their formation.

THC-COOH is very different from others, because it is created by the oxidation of 11-OH-THC.

What are the effects of 11-Oh-THC?

11 -OH-THC is the first active metabolite formed when THC is metabolized by the liver [1]. It is formed by the addition of a hydroxyl group (-oh) at position 11 of the central ring of THC. Its name therefore reflects this modification. 11-OH-THC is the most potent of the metabolites. Studies suggest thatit may be up to four times more potent than THC [2].

According to the prevention observatory, the effects of 11-OH-THC are more powerful when ingested, because it crosses the blood-brain barrier more effectively, resulting in more intense and prolonged effects3].

Indeed, studies have detected a stronger affinity with CB1 receptors, which could contribute to its greater psychoactive potency.

In terms of effects, 11-OH-THC appears to produce effects quite similar to THC, with a marked difference in potency. This also means that "bad trips" (paranoia, panic attacks, etc.) are potentially more frequent and more severe, as well as an increased heart rate (tachycardia) just minutes after ingestion. This means that 11-OH-THC is not only more potent than THC, but also acts more quickly.

 

What are the effects of 10-OH-THC?

10 -OH-THC is also an active metabolite formed when THC is metabolized by the liver, but it is much rarer and far less studied. As you might have guessed, the difference with 11-OH-THC lies in the addition of a hydroxyl group (-oh) at position 10, rather than position 11, of the central ring of THC.

Due to the limited interest in the molecule, very little is known about the actual effects of 10-OH-THC. It appears to have some affinity for CB1 and CB2 receptors, but much less pronounced than that of THC or 11-OH-THC. Indeed, 10-OH-THC seems to have a significantly lower psychoactive potency.

Some attribute sedative properties to it; however, although this may be possible, these effects are not documented by scientific research.

What are the effects of THC-COOH?

The last THC byproduct we will discuss is actually a byproduct created by the oxidation of 11-OH-THC. Since this is the most prevalent byproduct after THC consumption, the creation of THC-COOH is inevitable, although it is not a direct metabolite of THC. It is the final form of THC; it is in this form that it is stored until it is eliminated4]

To tell you how inevitable its creation is and in a fairly stable quantity after THC consumption: it is thanks to the detection of THC-COOH that screening tests can deduce THC consumption.

Unlike other metabolites, and like CBD, THC-COOH has no affinity for CB1 receptors. It also has no psychoactive effects, but may play a role in the analgesic and anti-inflammatory effects of cannabis.

 

Summary of the effects of THC metabolites

• 11-OH-THC is the main metabolite of THC. It is psychoactive and four times more potent than THC.
• 10-OH-THC is a minor metabolite. It is probably weak and not very psychoactive.
• THC-COOH is the oxidized form of 11-OH-THC. It is not psychoactive and is used as a screening marker.

11-OH-THC, 10-OH-THC and THC-COOH: are THC metabolites banned in Europe?

This is one of the topics of greatest interest to the CBD market right now: which molecules are legal, which are prohibited, and which can be sold. Regarding THC metabolites, the issue is complex.

In France, as in most European countries, legislation governing molecules does not stop at the molecule itself; it also regulates so-called secondary molecules, essentially synthetic molecules. Indeed, Article R.5132-86 of the Public Health Code states:

"The following are classified as narcotics: substances listed on the list of narcotics, as well as their esters, ethers, salts, isomers, analogues, and metabolites if they are capable of producing identical effects."

In Germany, the Neue-psychoaktive-Stoffe-Gesetz (NpSG) and in Italy, the DPR 309/1990 – Testo Unico sulle droghe (Single Drug Law), also operate on this principle of "functional analogy" ; a molecule too strongly linked to a molecule prohibited on a structural AND effects level is immediately prohibited.

This directly excludes 11-OH-THC, due to its effects being stronger than those of THC, but leaves considerable ambiguity regarding 10-OH-THC and even more so for THC-COOH. While research on 10-OH-THC is lacking, it could produce effects weaker or different enough from those of THC to circumvent the legislation.

As for THC-COOH, it has been studied much more extensively, and since it doesn't produce psychoactive effects, it could be perfectly legal. A THC metabolite, whether psychoactive or not, could provide an excellent selling point. It's therefore reasonable to wonder why it isn't sold in CBD shops, while HHC metabolites are currently available for purchase. Perhaps this is one of those "red lines" that retailers wouldn't dare cross for fear of a government response commensurate with their audacity.

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11-OH-THC, 10-OH-THC and THC-COOH in brief

Criteria	11-OH-THC	10-OH-THC	THC-COOH
Definition	First active metabolite of THC	THC active metabolite	Oxidized form of 11-OH-THC
Frequency	Main / Majority	Rare	Inevitable and stable after consumption
Psychoactivity	Very strong	Weak, not very psychoactive	Non-psychoactive
Effects	Stronger than THC	Little known	Few effects
Special feature	Produced in large quantities through the consumption of THC	Little studied, little scientific interest	Serves as a THC detection marker in tests
Legal status (France/EU)	Forbidden	Grey area	Grey area

 

Conclusion on THC metabolites

11 -OH-THC, 10-OH-THC, and THC-COOH are interesting molecules. Their effects vary: while the first is potentially four times more potent than THC, the last has virtually no effect.

This difference in effect could be felt at the level of European legislation concerning effective analogy. This does not, however, prevent some from selling 10-OH-HHC.

Indeed, taking advantage of the legal ambiguity, some, whether they are pioneers, intrepid or careless, or even all three, are already offering products containing 10-OH-THC.

It is highly likely that we will see the emergence of a new ban aimed at more explicitly regulating the by-products of HHC and THC, in all their forms and regardless of their effects.

We will keep you informed should this happen. In the meantime, thank you for reading and feel free to browse our blog to discover batchs of other interesting information about CBD and its world!