11-Hydroxy-THC

11-Hydroxy-Δ9-tetrahydrocannabinol (11-OH-Δ9-THC, alternatively numbered as 7-OH-Δ1-THC), usually referred to as 11-hydroxy-THC is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after Δ9-THC is consumed.

For the isomer of this chemical inherited from Δ8-tetrahydrocannabinol, see 11-Hydroxy-Delta-8-THC.
11-Hydroxy-THC
Clinical data
Drug classCannabinoid
Legal status
Legal status
Identifiers
  • (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.164.583
Chemical and physical data
FormulaC21H30O3
Molar mass330.468 g·mol−1
3D model (JSmol)
SMILES
  • 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 Y
  • Key:YCBKSSAWEUDACY-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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 dehydrogenase and CYP2C9 enzymes to form 11-nor-9-carboxy-THC (THC-COOH) which is inactive at the CB1 receptors; and further glucuronidated to form 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ9-THC-COOH-glu) in the liver, from where it is subsequently excreted through feces and urine (via bile from the liver). Both metabolites, along with THC, can be assayed in drug tests.

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.

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