## 11-Hydroxycannabinol (11-OH-THC): A Key Metabolite in Cannabis Research
11-hydroxycannabinol (11-OH-THC) is a **metabolite** of **tetrahydrocannabinol (THC)**, the primary psychoactive compound in cannabis. It's formed in the body after THC is ingested or inhaled, and it's actually **more potent than THC** in terms of binding to cannabinoid receptors.
**Here's why it's important for research:**
* **Understanding the Effects of Cannabis:** 11-OH-THC is a major contributor to the psychoactive effects of cannabis. Studying its mechanisms of action can help researchers understand how cannabis affects the brain and body.
* **Developing New Medications:** 11-OH-THC's high potency and unique properties could lead to the development of new medications targeting cannabinoid receptors. This could be beneficial for treating a range of conditions, such as chronic pain, nausea, and anxiety.
* **Investigating the Pharmacokinetics of THC:** 11-OH-THC's formation and elimination from the body are key aspects of THC's pharmacokinetics. Understanding these processes can help researchers develop more accurate and reliable drug testing methods.
* **Understanding the Role of Metabolites:** 11-OH-THC serves as an example of how metabolites can play significant roles in the effects of drugs. Studying these metabolites can provide valuable insights into the overall pharmacology of a substance.
**Further Research Areas:**
* **11-OH-THC's role in the therapeutic effects of cannabis:** Does it contribute to the therapeutic effects of cannabis, or does it simply contribute to the psychoactive effects?
* **The relationship between 11-OH-THC and tolerance:** Does the body develop tolerance to 11-OH-THC, and if so, how does this affect the long-term effects of cannabis?
* **The potential for 11-OH-THC to be used in drug development:** What are the potential therapeutic applications of 11-OH-THC, and how can it be safely and effectively used?
Overall, 11-OH-THC is an important molecule in cannabis research. It holds significant potential for advancing our understanding of cannabis and developing new therapies.
11-hydroxycannabinol: active metabolite of cannabinol; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 3082311 |
| CHEMBL ID | 109972 |
| MeSH ID | M0152621 |
| Synonym |
|---|
| 11-hydroxycannabinol |
| 30432-08-7 |
| 6h-dibenzo(b,d)pyran-9-methanol, 1-hydroxy-6,6-dimethyl-3-pentyl- |
| CHEMBL109972 , |
| 9-(hydroxymethyl)-6,6-dimethyl-3-pentylbenzo[c]chromen-1-ol |
| 9-hydroxymethyl-6,6-dimethyl-3-pentyl-6h-benzo[c]chromen-1-ol |
| bdbm50061112 |
| YDKZOUNVEIGJPO-UHFFFAOYSA-N |
| DTXSID60184517 |
| PD166018 |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Cannabinoid receptor 1 | Rattus norvegicus (Norway rat) | Ki | 0.1134 | 0.0002 | 0.5665 | 10.0000 | AID49492; AID49662 |
| Cannabinoid receptor 2 | Homo sapiens (human) | Ki | 0.0266 | 0.0000 | 0.4156 | 10.0000 | AID49843 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Cannabinoid receptor 1 | Rattus norvegicus (Norway rat) | EC50 (µMol) | 0.0581 | 0.0002 | 0.1921 | 1.9953 | AID49474 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| protein binding | Cannabinoid receptor 2 | Homo sapiens (human) |
| cannabinoid receptor activity | Cannabinoid receptor 2 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| plasma membrane | Cannabinoid receptor 2 | Homo sapiens (human) |
| dendrite | Cannabinoid receptor 2 | Homo sapiens (human) |
| extrinsic component of cytoplasmic side of plasma membrane | Cannabinoid receptor 2 | Homo sapiens (human) |
| perikaryon | Cannabinoid receptor 2 | Homo sapiens (human) |
| endoplasmic reticulum | Cannabinoid receptor 2 | Homo sapiens (human) |
| plasma membrane | Cannabinoid receptor 2 | Homo sapiens (human) |
| cytoplasm | Cannabinoid receptor 2 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID167518 | Number of rabbits convulsed at 4 mg/kg, iv out of 1 rabbit tested | 1982 | Journal of medicinal chemistry, May, Volume: 25, Issue:5 | Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids. |
| AID167512 | Number of rabbits convulsed at 2 mg/kg, iv out of 2 rabbits tested | 1982 | Journal of medicinal chemistry, May, Volume: 25, Issue:5 | Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids. |
| AID49662 | Binding to Cannabinoid receptor 1 using African green monkey (COS-7) cells transfected with the cDNA of rat CB1. | 1997 | Journal of medicinal chemistry, Sep-26, Volume: 40, Issue:20 | Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase. |
| AID49474 | Effective concentration for inhibition of Cannabinoid receptor 1-mediated adenylyl cyclase activity using African green monkey (COS-7) cells transfected with the cDNA of rat CB1 receptor | 1997 | Journal of medicinal chemistry, Sep-26, Volume: 40, Issue:20 | Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase. |
| AID167504 | Number of rabbits convulsed at 1 mg/kg, iv out of 4 rabbits tested | 1982 | Journal of medicinal chemistry, May, Volume: 25, Issue:5 | Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids. |
| AID49843 | Binding affinity to Cannabinoid receptor 2 using African green monkey (COS-7) cells Chinese hamster ovary(CHO) cells transfected with the cDNA of human CB2 | 1997 | Journal of medicinal chemistry, Sep-26, Volume: 40, Issue:20 | Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase. |
| AID165405 | Capability to induce convulsions in tetrahydrocannabinol-seizure susceptible (THC-SS) rabbit | 1982 | Journal of medicinal chemistry, May, Volume: 25, Issue:5 | Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids. |
| AID167492 | Number of rabbits convulsed at 0.5 mg/kg, iv out of 1 rabbit tested | 1982 | Journal of medicinal chemistry, May, Volume: 25, Issue:5 | Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids. |
| AID49694 | Inhibitory activity of 1 uM against human Cannabinoid receptor 2-mediated adenylyl cyclase using African green monkey (COS-7) cells transfected with the cDNA of human CB2 receptor | 1997 | Journal of medicinal chemistry, Sep-26, Volume: 40, Issue:20 | Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase. |
| AID49492 | Binding affinity for Cannabinoid receptor 1 using African green monkey (COS-7) cells transfected with the cDNA of rat brain synaptosomal membrane preparations. | 1997 | Journal of medicinal chemistry, Sep-26, Volume: 40, Issue:20 | Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 2 (40.00) | 18.7374 |
| 1990's | 1 (20.00) | 18.2507 |
| 2000's | 1 (20.00) | 29.6817 |
| 2010's | 1 (20.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.47) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 1 (20.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 4 (80.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||