Metabolism of tetrahydrocannabinol (THC) (Homo sapiens)

From WikiPathways

Revision as of 12:45, 2 February 2018 by DeSl (Talk | contribs)
Jump to: navigation, search
2323311, 22, 42253233MALCOPhase II metabolismMALDOConjugationP450 3AP450 2C911-nor-9-carboxy-THC11-oxo-THCTHC-COOH-glucuronideADH8-Hydroxy-delta-9-THC8,11-dihydroxy-delta-9-THC11-hydroxy-THCTHCCYP2C96-9Phase I metabolism


Description

Pathway on THC metabolism. Delta9-tetrahydrocannabinol (THC, also named delta1-tetrahydrocannabinol according to the monoterpenoid nomenclature), the primary hallucinogenic constituent of Cannabis sativa, is subject to hepatic metabolism primarily by hydroxylation.

Try the New WikiPathways

View approved pathways at the new wikipathways.org.

Quality Tags

Ontology Terms

 

Bibliography

View all...
  1. Maurer HH, Sauer C, Theobald DS; ''Toxicokinetics of drugs of abuse: current knowledge of the isoenzymes involved in the human metabolism of tetrahydrocannabinol, cocaine, heroin, morphine, and codeine.''; Ther Drug Monit, 2006 PubMed Europe PMC Scholia
  2. Hanisch S, Paulke A, Toennes SW; ''11-nor-9-carboxy-delta-9-tetrahydrocannabinol glucuronide exhibits acyl-migration isomers.''; J Pharm Biomed Anal, 2017 PubMed Europe PMC Scholia
  3. Skopp G, Pötsch L; ''Stability of 11-nor-delta(9)-carboxy-tetrahydrocannabinol glucuronide in plasma and urine assessed by liquid chromatography-tandem mass spectrometry.''; Clin Chem, 2002 PubMed Europe PMC Scholia
  4. Kim JY, Kwon W, Kim HS, Suh S, In MK; ''Estimation of measurement uncertainty for the quantification of 11-nor-delta 9-tetrahydrocannabinol-9-carboxylic acid and its glucuronide in urine using liquid chromatography-tandem mass spectrometry.''; J Anal Toxicol, 2014 PubMed Europe PMC Scholia
  5. Pichini S, Marchei E, Martello S, Gottardi M, Pellegrini M, Svaizer F, Lotti A, Chiarotti M, Pacifici R; ''Identification and quantification of 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid glucuronide (THC-COOH-glu) in hair by ultra-performance liquid chromatography tandem mass spectrometry as a potential hair biomarker of cannabis use.''; Forensic Sci Int, 2015 PubMed Europe PMC Scholia
  6. Watanabe K, Matsunaga T, Kimura T, Funahashi T, Funae Y, Ohshima T, Yamamoto I; ''Major cytochrome P450 enzymes responsible for microsomal aldehyde oxygenation of 11-oxo-Delta8-tetrahydrocannabinol and 9-anthraldehyde in human liver.''; Drug Metab Pharmacokinet, 2002 PubMed Europe PMC Scholia
  7. Jenkins, AMANDA J., EDWARD J. Cone; ''Drug abuse handbook.''; CRC Press, 1998
  8. Regan SL, Maggs JL, Hammond TG, Lambert C, Williams DP, Park BK; ''Acyl glucuronides: the good, the bad and the ugly.''; Biopharm Drug Dispos, 2010 PubMed Europe PMC Scholia
  9. Huestis MA; ''Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol.''; Handb Exp Pharmacol, 2005 PubMed Europe PMC Scholia

History

View all...
CompareRevisionActionTimeUserComment
125300view17:36, 31 January 2023LarsgwAdd ISBN to reference
124805view21:37, 11 December 2022AlexanderPicofixed citations
124784view06:39, 11 December 2022AlexanderPicofixed citations
117157view09:46, 18 May 2021EweitzModified title
106782view13:26, 17 September 2019MaintBotHMDB identifier normalization
98304view05:13, 19 August 2018EgonwReplaced the DrugBank metabolite ID with a Wikidata ID with links.
98303view05:11, 19 August 2018EgonwRemoved duplicate fields in Biopax publicationXref.
95899view12:54, 2 February 2018DeSlModified description
95896view12:47, 2 February 2018DeSlOntology Term : 'phase I biotransformation pathway via cytochrome P450' added !
95895view12:46, 2 February 2018DeSlOntology Term : 'xenobiotic metabolic pathway' added !
95894view12:45, 2 February 2018DeSlChanged layout
95893view12:43, 2 February 2018DeSlAdded more literature refs, for metabolite I couldn't find an ID for
95892view12:21, 2 February 2018DeSlAdded new nodes, more literature references etc.
95853view17:31, 26 January 2018KhanspersOntology Term : 'drug pathway' added !
95852view17:29, 26 January 2018KhanspersModified description
95596view00:40, 7 January 2018MaintBotModified title
95203view15:36, 22 November 2017DeSlNew pathway

External references

DataNodes

View all...
NameTypeDatabase referenceComment
11-hydroxy-THCMetabolite37482 (PubChem-compound)
11-nor-9-carboxy-THCMetabolite107885 (PubChem-compound)
11-oxo-THCMetabolite124158 (PubChem-compound)
8,11-dihydroxy-delta-9-THCMetaboliteDBMET01220 (DrugBank)
8-Hydroxy-delta-9-THCMetaboliteHMDB60910 (HMDB)
ADHProtein1.1.1.1 (Enzyme Nomenclature) alcohol dehydrogenase
CYP2C9ProteinENSG00000138109 (Ensembl)
P450 2C9ProteinP11712 (Uniprot-TrEMBL)
P450 3AProteinP08684 (Uniprot-TrEMBL)
THC-COOH-glucuronideMetabolite
  • Acyl glucuronidatised form
  • Name: 11-nor-ÃŽâ€�9-tetrahydrocannabinol-9-carboxylic acid glucuronide
THCMetabolite16078 (PubChem-compound) delta9-tetrahydrocannabinol

Annotated Interactions

No annotated interactions

Retrieved from "https://classic.wikipathways.org/index.php/Pathway:WP4174"
Personal tools