| Revision as of 16:47, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,049 edits Saving copy of the {{drugbox}} taken from revid 455739087 of page 11-Hydroxy-THC for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 12:54, 11 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
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{{Short description|Active metabolite of Δ9-THC}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{For|the isomer of this chemical inherited from ]|11-Hydroxy-Delta-8-THC}} |
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{{Drugbox |
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{{Infobox drug |
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| verifiedrevid = 451546660 |
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| verifiedrevid = 477208799 |
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| IUPAC_name = (6''aR'',10''aR'')-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6''a'',7,8,10''a''-tetrahydro-6''H''-benzochromen-1-ol |
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| IUPAC_name = (6''aR'',10''aR'')-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6''a'',7,8,10''a''-tetrahydro-6''H''-benzochromen-1-ol |
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| image = 11-OH-THC.svg |
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| image = 11-OH-THC.svg |
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| image_class = skin-invert-image |
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| width = 250px |
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| width = 250px |
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| image2 = 11-Hydroxy-THC-3D-balls.png |
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| alt2 = 11-Hydroxy-THC molecule |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| legal_status = |
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| legal_UK = Class B |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 36557-05-8 --> |
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| CAS_number = 36557-05-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9VY04N5SLB |
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| PubChem = 37482 |
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| PubChem = 37482 |
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| KEGG = C22778 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 34385 |
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| ChemSpiderID = 34385 |
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| class = ] |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=21 | H=30 | O=3 |
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| C=21 | H=30 | O=3 |
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| molecular_weight = 330.461 g/mol |
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| smiles = Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC |
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| smiles = Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC |
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| InChI = 1/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 |
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| InChIKey = YCBKSSAWEUDACY-UHFFFAOYAL |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey = YCBKSSAWEUDACY-UHFFFAOYSA-N |
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| StdInChIKey = YCBKSSAWEUDACY-UHFFFAOYSA-N |
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}} |
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'''11-Hydroxy-Δ<sup>9</sup>-tetrahydrocannabinol''' ('''11-OH-Δ<sup>9</sup>-THC''', alternatively numbered as '''7-OH-Δ<sup>1</sup>-THC'''), usually referred to as '''11-hydroxy-THC''' is the main active ] of ] (THC), which is formed in the body after Δ<sup>9</sup>-THC 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 = 1415–1435 | date = August 2007 | pmid = 17468860 | doi = 10.1007/s00216-007-1271-6 | s2cid = 32917584 }}</ref><ref name=Huestis2005>{{cite book | vauthors = Huestis MA | title = Cannabinoids | chapter = Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol | series = Handbook of Experimental Pharmacology | volume = 168 | pages = 657–690 | date = 2005 | issue = <!-- none --> | pmid = 16596792 | doi = 10.1007/3-540-26573-2_23 | isbn = 3-540-22565-X }}</ref> |
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After ], THC is ] inside the body by ] enzymes such as ] and ] into 11-hydroxy-THC and then further metabolized by ] {{which|date=April 2024}} and ] enzymes to form ] (THC-COOH) which is inactive at the CB<sub>1</sub> receptors;<ref name=Huestis2005/> and further ] to form 11-nor-Δ<sup>9</sup>-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ<sup>9</sup>-THC-COOH-glu)<ref name="Stout_2014">{{cite journal | vauthors = Stout SM, Cimino NM | title = Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review | journal = Drug Metabolism Reviews | volume = 46 | issue = 1 | pages = 86–95 | date = February 2014 | pmid = 24160757 | doi = 10.3109/03602532.2013.849268 | s2cid = 29133059 | url = https://zenodo.org/record/1093138 }}</ref> in the liver, from where it is subsequently excreted through feces and urine (via ] from the liver).<ref name="Grotenhermen_2003">{{cite journal | vauthors = Grotenhermen F | title = Pharmacokinetics and pharmacodynamics of cannabinoids | journal = Clinical Pharmacokinetics | volume = 42 | issue = 4 | pages = 327–360 | date = 2003 | pmid = 12648025 | doi = 10.2165/00003088-200342040-00003 | s2cid = 25623600 }}</ref> Both metabolites, along with THC, can be assayed in drug tests.<ref name=Kraemer2007/> |
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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.<ref name="Huestis_1992">{{cite journal | vauthors = Huestis MA, Henningfield JE, Cone EJ | title = Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana | journal = Journal of Analytical Toxicology | volume = 16 | issue = 5 | pages = 276–282 | date = 1992 | pmid = 1338215 | doi = 10.1093/jat/16.5.276 }}</ref><ref name="Karschner_2009">{{cite journal | vauthors = Karschner EL, Schwilke EW, Lowe RH, Darwin WD, Herning RI, Cadet JL, Huestis MA | title = Implications of plasma Delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers | journal = Journal of Analytical Toxicology | volume = 33 | issue = 8 | pages = 469–477 | date = October 2009 | pmid = 19874654 | pmc = 3159863 | doi = 10.1093/jat/33.8.469 }}</ref> |
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== Pharmacology == |
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Like Δ<sup>9</sup>-THC, 11-hydroxy-THC is a partial agonist at the ] ], but with significantly higher ] (K<sub>i</sub> = 0.37 nM compared to Δ<sup>9</sup>-THC K<sub>i</sub> = 35 nM).<ref name="Zagzoog2022">{{cite journal | vauthors = Zagzoog A, Cabecinha A, Abramovici H, Laprairie RB | title = Modulation of type 1 cannabinoid receptor activity by cannabinoid by-products from ''Cannabis sativa'' and non-cannabis phytomolecules | journal = Frontiers in Pharmacology | volume = 13 | pages = 956030 | date = 26 August 2022 | pmid = 36091813 | doi = 10.3389/fphar.2022.956030 | pmc = 9458935 | doi-access = free }}</ref> With respect to ] inhibition at CB<sub>1</sub> it displays a similar efficacy to that of Δ<sup>9</sup>-THC (EC<sub>50</sub> = 11 nM vs. EC<sub>50</sub> = 5.2 nM, respectively), but a lower maximum response (E<sub>max</sub> = 28% vs. E<sub>max</sub> = 70%).<ref name="Zagzoog2022" /> |
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== Research == |
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In an '']'' analysis by the ] on ] it was found that 11-OH-Δ<sup>9</sup>-THC had the 3rd highest ] inhibitor activity against ] out of all the cannabinoids tested within that study but not as high as the ] ] (56% for 11-OH-Δ<sup>9</sup>-THC vs. 100% for GC376).<ref>{{cite journal | vauthors = Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H | title = Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity | journal = Molecules | volume = 27 | issue = 18 | page = 6127 | date = September 2022 | pmid = 36144858 | pmc = 9502466 | doi = 10.3390/molecules27186127 | doi-access = free }}</ref> |
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== See also == |
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== References == |
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{{reflist}} |
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{{Cannabinoids}} |
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{{Cannabinoidergics}} |
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{{DEFAULTSORT:Hydroxy-THC, 11-}} |
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