11-Hydroxy-Δ9-tetrahydrocannabinol (11-OH-THC), usually referred to as 11-hydroxy-THC, is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after cannabis is consumed.
|Chemical and physical data|
|Molar mass||330.461 g/mol|
|3D model (JSmol)|
|(what is this?)|
Fresh cannabis contains tetrahydrocannabinolic acid (THCA), which is converted into THC after heating and then metabolized by the body into 11-hydroxy-THC and then into 11-nor-9-carboxy-THC; both compounds can be glucuronidated and mainly excreted into urine. Both compounds, along with THC, are assayed in blood tests.
Based on one study from 1972 that directly compared administration of THC and 11-hydroxy-THC to twenty men, drug effects were equal in potency, but were perceived more rapidly with 11-hydroxy-THC than with THC, and 11-hydroxy-THC was cleared from blood faster; this suggests that 11-hydroxy-THC diffuses into the brain more readily than THC, or that THC remains bound to proteins in blood longer. In sheep, dogs, and monkeys, THC crosses the placenta more efficiently than 11-hydroxy-THC.
- Kraemer, T; Paul, LD (August 2007). "Bioanalytical procedures for determination of drugs of abuse in blood". Analytical and bioanalytical chemistry. 388 (7): 1415–35. doi:10.1007/s00216-007-1271-6. PMID 17468860.
- Huestis, MA (2005). "Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol". Handbook of experimental pharmacology (168): 657–90. PMID 16596792.