Metabolism of tetrahydrocannabinol (THC) (Homo sapiens)

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1414421, 21, 51134144MALCOPhase 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.

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Quality Tags

Ontology Terms

 

Bibliography

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  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

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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

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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-Δ9-tetrahydrocannabinol-9-carboxylic acid glucuronide
THCMetabolite16078 (PubChem-compound) delta9-tetrahydrocannabinol

Annotated Interactions

No annotated interactions

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