11-Hydroxy-THC

11-Hydroxy-THC
Clinical data
Other names	11-OH-Δ9-THC; 7-OH-Δ1-THC; 11-hydroxy-THC
Drug class	Cannabinoid
ATC code	None;
Legal status
Legal status	UK: Class B;
Identifiers
	IUPAC name (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol;
CAS Number	36557-05-8 ;
PubChem CID	37482;
ChemSpider	34385 ;
UNII	9VY04N5SLB;
KEGG	C22778;
CompTox Dashboard (EPA)	DTXSID50190061 ;
ECHA InfoCard	100.164.583
Chemical and physical data
Formula	C21H30O3
Molar mass	330.468 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC;
	InChI 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 ; Key:YCBKSSAWEUDACY-UHFFFAOYSA-N ;
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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 its consumed.

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.