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11-Hydroxy-Δ9-tetrahydrocannabinol (11-OH-THC) is the main active metabolite of Tetrahydrocannabinol (THC) which is formed in the body after cannabis is consumed.[1] The conversion from THC to 11-OH-THC is relatively high when cannabis is consumed in the form of cannabis edibles and, compared to oral consumption, lower when it is smoked or vaped.[2] 11-OH-THC is more potent than THC and crosses the blood–brain barrier more easily.[3][4] 11-Hydroxy-THC has been shown to be active in its own right.[5][6] This might partially explain the biphasic effects of cannabis, whereby some effects such as increased appetite tend to be delayed rather than occurring immediately when the drug is consumed.[7]

11-Hydroxy-THC
11-OH-THC.svg
11-Hydroxy-THC molecule
Identifiers
CAS Number
PubChem CID
ChemSpider
ECHA InfoCard 100.164.583
Chemical and physical data
Formula C21H30O3
Molar mass 330.461 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)
Preparing cannabis for consumption as bhang

Fresh cannabis contains Tetrahydrocannabinolic acid (THCA), which is converted into THC after heating and then metabolized by the body into 11-Hydroxy-THC.[8][9][10][11] Peak THC concentrations are lower after eating/drinking cannabis than after administration by smoking or vaping, but conversely, 11-OH-THC/THC ratios are higher after eating/drinking than after smoking cannabis.[12] After administration through eating or drinking, approximately equal quantities of THC and 11-OH-THC are formed, whereas 11-OH-THC is a minor constituent after administration by intravenous or smoking routes.[13] Because edible doses are processed by the liver before entering the bloodstream, THC consumed as edibles produces high levels of 11-OH-THC, while smoked cannabis, which goes directly from the lungs to the brain via the bloodstream and does not enter the liver,[14] produces lower levels.[15]

11-Hydroxy-THC is subsequently metabolised further to 11-nor-9-carboxy-THC, which is not psychoactive but might still play a role in the analgesic and anti-inflammatory effects of cannabis.

ReferencesEdit

  1. ^ Johnson JR, Jennison TA, Peat MA, Foltz RL (1984). "Stability of delta 9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC in blood and plasma". Journal of analytical toxicology. 8 (5): 202–4. PMID 6094914. doi:10.1093/jat/8.5.202. 
  2. ^ Government Marijuana Researcher Speaks Favorably About Marijuana's Medical Utility NORML September 26, 1996.
  3. ^ Possible hepatotoxicity of chronic marijuana usage Sao Paulo Med. J. vol.122 no.3 São Paulo May 2004.
  4. ^ Possible hepatotoxicity of chronic marijuana usage Sao Paulo Med. J. vol.122 no.3 São Paulo May 2004.
  5. ^ Turkanis SA, Karler R (1988). "Changes in neurotransmitter release at a neuromuscular junction of the lobster caused by cannabinoids". Neuropharmacology. 27 (7): 737–42. PMID 2901683. doi:10.1016/0028-3908(88)90083-4. 
  6. ^ Hollister LE, Gillespie HK (1975). "Action of delta-9-tetrahydrocannabinol. An approach to the active metabolite hypothesis". Clin. Pharmacol. Ther. 18 (6): 714–9. PMID 1204277. 
  7. ^ Lemberger, L; Martz, R; Rodda, B; Forney, R; Rowe, H (1973). "Comparative Pharmacology of Δ9-Tetrahydrocannabinol and its Metabolite, 11-OH-Δ9-Tetrahydrocannabinol". The Journal of Clinical Investigation. 52 (10): 2411–7. PMC 302499 . PMID 4729039. doi:10.1172/JCI107431. 
  8. ^ Baker PB, Taylor BJ, Gough TA (Jun 1981), "The tetrahydrocannabinol and tetrahydrocannabinolic acid content of cannabis products", Journal of Pharmacy and Pharmacology, 33 (6): 369–72, PMID 6115009, doi:10.1111/j.2042-7158.1981.tb13806.x 
  9. ^ Sirikantaramas S, Morimoto S, Shoyama Y, Ishikawa Y, Wada Y, Shoyama Y, Taura F (2004-09-17), "The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.", Journal of Biological Chemistry, 279 (38): 39767–74, PMID 15190053, doi:10.1074/jbc.M403693200 
  10. ^ Moore C, Rana S, Coulter C (2007-06-01), "Simultaneous identification of 2-carboxy-tetrahydrocannabinol, tetrahydrocannabinol, cannabinol and cannabidiol in oral fluid", J Chromatogr B Analyt Technol Biomed Life Sci., 852 (1-2): 459–64, PMID 17321807, doi:10.1016/j.jchromb.2007.02.016 
  11. ^ Taura F. (Jun 2009), "Studies on tetrahydrocannabinolic acid synthase that produces the acidic precursor of tetrahydrocannabinol, the pharmacologically active cannabinoid in marijuana", Drug Discoveries and Therapeutics, 3 (3): 83–7, PMID 22495534 
  12. ^ Schwilke EW, Schwope DM, Karschner EL, et al. (December 2009). "Δ9-Tetrahydrocannabinol (THC), 11-Hydroxy-THC, and 11-Nor-9-carboxy-THC Plasma Pharmacokinetics during and after Continuous High-Dose Oral THC". Clin. Chem. 55: 2180–9. PMC 3196989 . PMID 19833841. doi:10.1373/clinchem.2008.122119. 
  13. ^ Wall ME, Perez-Reyes M. "The metabolism of delta 9-tetrahydrocannabinol and related cannabinoids in man". J Clin Pharmacol. 21: 178S–189S. PMID 6271823. doi:10.1002/j.1552-4604.1981.tb02594.x. 
  14. ^ Dazed & Infused: Five legit reasons why an edible’s high is unpredictable
  15. ^ Government Marijuana Researcher Speaks Favorably About Marijuana's Medical Utility NORML September 26, 1996.