11-Hydroxy-THC: Difference between revisions

Latest revision as of 18:54, 22 March 2025

Metabolite of THC

11-Hydroxy-THC (11-OH-THC) is a metabolite of tetrahydrocannabinol (THC), the primary psychoactive component of cannabis. It is formed in the body after the consumption of THC, primarily through the process of metabolism in the liver.

Formation and Metabolism[edit]

When THC is consumed, it is absorbed into the bloodstream and transported to the liver. In the liver, THC undergoes hydroxylation to form 11-Hydroxy-THC. This process is facilitated by the cytochrome P450 enzyme system, particularly the CYP2C9 and CYP3A4 isoenzymes. 11-Hydroxy-THC is further metabolized into 11-nor-9-carboxy-THC (THC-COOH), which is an inactive metabolite and is eventually excreted from the body.

Pharmacology[edit]

11-Hydroxy-THC is known to be more potent than THC itself. It has a higher affinity for the cannabinoid receptors, particularly the CB1 receptors in the central nervous system. This increased potency is believed to contribute to the stronger psychoactive effects experienced when cannabis is consumed orally, as opposed to inhalation. The onset of effects is slower with oral consumption due to the time required for metabolism, but the effects are often more intense and longer-lasting.

Effects[edit]

The effects of 11-Hydroxy-THC are similar to those of THC, including euphoria, altered perception, and cognitive impairment. However, due to its increased potency, the psychoactive effects can be more pronounced. Users may experience heightened anxiety or paranoia, especially at higher doses.

Detection in the Body[edit]

11-Hydroxy-THC can be detected in the body through various drug testing methods. It is often measured in blood and urine tests to determine recent cannabis use. The presence of 11-Hydroxy-THC indicates that THC has been metabolized, and its levels can provide information about the timing and extent of cannabis consumption.

Clinical Significance[edit]

Understanding the role of 11-Hydroxy-THC is important in both clinical and forensic settings. It helps in assessing the psychoactive effects of cannabis and in interpreting drug test results. Additionally, research into 11-Hydroxy-THC and its effects can contribute to the development of new therapeutic applications for cannabinoids.

Related Pages[edit]

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-=='''What is {{PAGENAME}}?'''==
+{{Short description|Metabolite of THC}}
+{{DISPLAYTITLE:11-Hydroxy-THC}}
 [[File:11-OH-THC.svg|thumb|11-Hydroxy-THC]]
-* It is the active metabolite of [[Tetrahydrocannabinol]] (THC), which is formed in the body after decarboxylated cannabis is consumed<ref name=Kraemer2007>{{cite journal | vauthors = Kraemer T, Paul LD | title = Bioanalytical procedures for determination of drugs of abuse in blood | journal = Analytical and Bioanalytical Chemistry | volume = 388 | issue = 7 | pages = 1415–35 | date = August 2007 | pmid = 17468860 | doi = 10.1007/s00216-007-1271-6 | s2cid = 32917584 }}</ref><ref name=Huestis2005>{{cite journal | vauthors = Huestis MA | title = Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol | journal = Handbook of Experimental Pharmacology | volume = 168 | issue = 168 | pages = 657–90 | date = 2005 | pmid = 16596792 | doi = 10.1007/3-540-26573-2_23 | isbn = 3-540-22565-X }}</ref>.
+'''11-Hydroxy-THC''' (11-OH-THC) is a [[metabolite]] of [[tetrahydrocannabinol]] (THC), the primary psychoactive component of [[cannabis]]. It is formed in the body after the consumption of THC, primarily through the process of [[metabolism]] in the [[liver]].
-*'''IUPAC Name''': ''9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol''
-*'''InChI''': ''InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3''
-*'''InChI Key''': ''YCBKSSAWEUDACY-UHFFFAOYSA-N''
-*'''Canonical SMILES''': ''CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)CO)O''
-*'''Molecular formula''': ''C21H30O3''
-*'''Molecular weight''': ''330.5 g·mol−1''
-*'''Synonyms''':
-# ''26108-40-7''
-# ''11-Hydroxy-delta(9)-thc''
-# ''6a,7,8,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo(b,d)pyran-9-methanol''
-# ''7-Hydroxy-delta(1)-tetrahydrocannabinol''
-# ''6a,7,8,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-methanol''
-# ''11-Hydroxy-delta-9-THC''
-# ''SCHEMBL997050''
-# ''NIOSH/HP6900000''
-# ''DTXSID20948995''
-# ''6H-Dibenzo[b,d]pyran-9-methanol, 6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-''
-# ''HP69000000''
-# ''11-Hydroxy-delta(sup 9)-tetrahydrocannabinol''
-# ''L000048''
-# ''Q722962''
-# ''6,6-Dimethyl-1-hydroxy-3-pentyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,d)pyran-9-methanol''
-# ''6H-Dibenzo(b,d)pyran-9-methanol, 6a,7,8,10a-tetrahydro-6,6-dimethyl-1-hydroxy-3-pentyl-''
-# ''9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol''
-# ''9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol #''
-# ''9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-dibenzo[b,d]pyran-1-ol''
-# ''(+/-)-11-Hydroxy-Delta9-THC solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material''
-# ''(+/-)-11-Hydroxy-Delta9-THC solution, 100 mug/mL in methanol, ampule of 1 mL, certified reference material''
-<ref>National Center for Biotechnology Information (2021). PubChem Compound Summary for CID 37482, 11-Hydroxy-THC. Retrieved August 2, 2021 from <nowiki>https://pubchem.ncbi.nlm.nih.gov/compound/11-Hydroxy-THC</nowiki>.</ref>
-==References==
+==Formation and Metabolism==
-{{reflist}}
+When THC is consumed, it is absorbed into the bloodstream and transported to the liver. In the liver, THC undergoes [[hydroxylation]] to form 11-Hydroxy-THC. This process is facilitated by the [[cytochrome P450]] enzyme system, particularly the CYP2C9 and CYP3A4 isoenzymes. 11-Hydroxy-THC is further metabolized into 11-nor-9-carboxy-THC (THC-COOH), which is an inactive metabolite and is eventually excreted from the body.
+==Pharmacology==
+-Hydroxy-THC is known to be more potent than THC itself. It has a higher affinity for the [[cannabinoid receptor]]s, particularly the [[CB1 receptor]]s in the [[central nervous system]]. This increased potency is believed to contribute to the stronger psychoactive effects experienced when cannabis is consumed orally, as opposed to inhalation. The onset of effects is slower with oral consumption due to the time required for metabolism, but the effects are often more intense and longer-lasting.
+==Effects==
+The effects of 11-Hydroxy-THC are similar to those of THC, including [[euphoria]], altered perception, and [[cognitive impairment]]. However, due to its increased potency, the psychoactive effects can be more pronounced. Users may experience heightened [[anxiety]] or [[paranoia]], especially at higher doses.
+==Detection in the Body==
+-Hydroxy-THC can be detected in the body through various [[drug testing]] methods. It is often measured in [[blood]] and [[urine]] tests to determine recent cannabis use. The presence of 11-Hydroxy-THC indicates that THC has been metabolized, and its levels can provide information about the timing and extent of cannabis consumption.
+==Clinical Significance==
+Understanding the role of 11-Hydroxy-THC is important in both clinical and forensic settings. It helps in assessing the psychoactive effects of cannabis and in interpreting drug test results. Additionally, research into 11-Hydroxy-THC and its effects can contribute to the development of new therapeutic applications for cannabinoids.
+==Related Pages==
+* [[Tetrahydrocannabinol]]
+* [[Cannabinoid receptor]]
+* [[Metabolism]]
+* [[Cytochrome P450]]
+* [[Cannabis]]
 {{Cannabinoids}}
 {{Cannabinoidergics}}
 {{pharma-stub}}
 [[Category:Cannabinoids]]
 [[Category:Benzochromenes]]