Misplaced Pages

11-Hydroxy-THC: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editNext edit →Content deleted Content addedVisualWikitext
Revision as of 21:17, 4 January 2023 editSativa Inflorescence (talk | contribs)Extended confirmed users524 edits →Pharmacology: Not sure this financial report is a reliable source← Previous edit Revision as of 02:02, 5 January 2023 edit undoSativa Inflorescence (talk | contribs)Extended confirmed users524 edits overhaul. see talkNext edit →
Line 40: Line 40:
}} }}


'''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 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 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 = 657–690 | date = 2005 | pmid = 16596792 | doi = 10.1007/3-540-26573-2_23 | isbn = 3-540-22565-X }}</ref> '''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).<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 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 = 657–690 | date = 2005 | pmid = 16596792 | doi = 10.1007/3-540-26573-2_23 | isbn = 3-540-22565-X }}</ref>


After ], THC is ] inside the body by ] enzymes such as ] and ] into 11-hydroxy-THC and then further metabolized by the ] and ] enzyme to form ] (THC-COOH) which is inactive at the CB1 receptors;<ref name=Huestis2005/> and further ] to form 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid glucuronide (delta-9-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> where it is excreted in both feces and urine.<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 compounds, along with THC, can be assayed in drug tests.<ref name=Kraemer2007/> After ], THC is ] inside the body by ] enzymes such as ] and ] into 11-hydroxy-THC and then further metabolized by the ] and ] enzyme to form ] (THC-COOH) which is inactive at the CB1 receptors;<ref name=Huestis2005/> and further ] to form 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid glucuronide (delta-9-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> where it is excreted in both feces and urine.<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 compounds, along with THC, can be assayed in drug tests.<ref name=Kraemer2007/>


THC administered orally results in higher 11-OH-THC plasma concentration compared to smoking. <ref name="pertwee">{{cite book |last=Pertwee |first=Robert|date=2005 |title=Cannabinoids Handbook of Experimental Pharmacology volume 168|url= |location=Germany |publisher=Springer |page=667 |isbn=3-540-22565-X}}</ref>
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>

== Pharmacology ==
In an analysis by the ] on ] it was found that 11-OH-D9-THC had the 3rd highest ] inhibitor activity against ] out of all the cannabinoids tested within that study but not as high as the ] ] (56% 11-OH-D9-THC) vs 100% GC376). <ref>https://www.mdpi.com/1420-3049/27/18/6127</ref>

A 2015 report published by the Colorado Department of revenue found that the pharmacokinetic equivalency of Delta-9-THC to 11-Hydroxy-Δ9-tetrahydrocannabinol is 1 to 5.71.<ref>{{cite journal |last1=Orens |first1=Adam |title=Marijuana Equivalency in Portion and Dosage |date=August 10, 2015 |page=7 |doi=10.13140/RG.2.2.30577.28004 |url=https://www.researchgate.net/publication/316977045 |access-date=27 November 2022}}</ref>{{Citation needed|reason=not published by a scientific or medical organization|date=January 2023}}


== See also == == See also ==

Revision as of 02:02, 5 January 2023

Chemical compound Pharmaceutical compound
11-Hydroxy-THC
11-Hydroxy-THC molecule
Clinical data
Drug classCannabinoid
Legal status
Legal status
Identifiers
IUPAC name
  • (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzochromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.164.583 Edit this at Wikidata
Chemical and physical data
FormulaC21H30O3
Molar mass330.468 g·mol
3D model (JSmol)
SMILES
  • Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC
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
  • Key:YCBKSSAWEUDACY-UHFFFAOYSA-N
  (what is this?)  (verify)

11-Hydroxy-Δ-tetrahydrocannabinol (11-OH-Δ-THC, alternatively numbered as 7-OH-Δ-THC), usually referred to as 11-hydroxy-THC, is the main active metabolite of tetrahydrocannabinol (THC).

After cannabis consumption, THC is metabolized inside the body by cytochrome P450 enzymes such as CYP2C9 and CYP3A4 into 11-hydroxy-THC and then further metabolized by the dehydrogenase and CYP2C9 enzyme to form 11-nor-9-carboxy-THC (THC-COOH) which is inactive at the CB1 receptors; and further glucuronidated 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.

THC administered orally results in higher 11-OH-THC plasma concentration compared to smoking.

See also

References

  1. ^ Kraemer T, Paul LD (August 2007). "Bioanalytical procedures for determination of drugs of abuse in blood". Analytical and Bioanalytical Chemistry. 388 (7): 1415–1435. doi:10.1007/s00216-007-1271-6. PMID 17468860. S2CID 32917584.
  2. ^ Huestis MA (2005). "Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol". Handbook of Experimental Pharmacology. 168 (168): 657–690. doi:10.1007/3-540-26573-2_23. ISBN 3-540-22565-X. PMID 16596792.
  3. Stout SM, Cimino NM (February 2014). "Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review". Drug Metabolism Reviews. 46 (1): 86–95. doi:10.3109/03602532.2013.849268. PMID 24160757. S2CID 29133059.
  4. Grotenhermen F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clinical Pharmacokinetics. 42 (4): 327–360. doi:10.2165/00003088-200342040-00003. PMID 12648025. S2CID 25623600.
  5. Pertwee, Robert (2005). Cannabinoids Handbook of Experimental Pharmacology volume 168. Germany: Springer. p. 667. ISBN 3-540-22565-X.
Cannabinoids
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
Allosteric CBRTooltip Cannabinoid receptor ligands
Endocannabinoid
enhancers
(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
Cannabinoid receptor modulators
Receptor
(ligands)
CB1Tooltip Cannabinoid receptor type 1
Agonists
(abridged,
full list)
Inverse agonists
Antagonists
CB2Tooltip Cannabinoid receptor type 2
Agonists
Antagonists
NAGly
(GPR18)
Agonists
Antagonists
GPR55
Agonists
Antagonists
GPR119
Agonists
Transporter
(modulators)
eCBTsTooltip Endocannabinoid transporter
Enzyme
(modulators)
FAAHTooltip Fatty acid amide hydrolase
MAGL
ABHD6
ABHD12
Others
  • Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272 (FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
Categories: