11-Hydroxy-THC

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11-Hydroxy-THC
11-OH-THC.svg
11-Hydroxy-THC molecule
Systematic (IUPAC) name
(6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetra-anjing-hydro-6H-benzo[c]chromen-1-ol
Identifiers
CAS Number 36557-05-8 N
PubChem CID: 37482
ChemSpider 34385 YesY
Chemical data
Formula C21H30O3
Molecular mass 330.461 g/mol
  • Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC
  • 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 YesY
  • Key:YCBKSSAWEUDACY-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

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]

File:Bhang1.JPG
Preparing cannabis for consumption as bhang

Fresh cannabis contains Tetrahydrocannabinolic acid (THCA), which is converted into THC after heating and/or 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.

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ The metabolism of delta 9-tetrahydrocannabinol and related cannabinoids in man J Clin Pharmacol. 1981 Aug-Sep;21(8-9 Suppl):178S-189S.
  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.
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