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 OC1=C2[C@]3([C@](C(C)(C)OC2=CC(CCCCC)=C1)(CCC(CO)=C3)[H])[H];
	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 within cannabis culture, is the main active metabolite of tetrahydrocannabinol (THC), the major psychoactive substance in marijuana.

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. Both metabolites can be assayed in drug tests.

11-hydroxy-THC is formed after human consumption of THC containing products regardless of administration route, although levels of 11-hydroxy-THC are typically higher when cannabis products are eaten instead of inhaled.