Page last updated: 2024-12-06

11-hydroxy-delta(9)-tetrahydrocannabinol

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Description

## 11-hydroxy-delta(9)-tetrahydrocannabinol (11-OH-THC)

11-hydroxy-delta(9)-tetrahydrocannabinol, often shortened to 11-OH-THC, is a **metabolite** of delta-9-tetrahydrocannabinol (THC), the primary psychoactive compound in cannabis. It's formed in the liver by enzymes called **cytochrome P450** after THC is ingested.

**Why is 11-OH-THC important for research?**

1. **Potency:** 11-OH-THC is **significantly more potent** than THC, meaning it binds to cannabinoid receptors in the brain with greater affinity and produces stronger psychoactive effects. This is why many people experience a high a few hours after consuming cannabis, even though THC levels may be declining.

2. **Long-term effects:** Because it's a metabolite, 11-OH-THC can remain in the body for a **longer period** than THC, potentially contributing to the lingering effects of cannabis use. This is important to consider for long-term users and for understanding the potential long-term effects of cannabis.

3. **Medical applications:** 11-OH-THC is being studied for its potential **therapeutic benefits** in conditions like chronic pain and anxiety. It may offer a more potent and longer-lasting effect than THC for certain patients.

4. **Cannabis testing:** 11-OH-THC is often used as a **marker for recent cannabis use** in drug tests because it persists in the body for a longer time than THC.

5. **Understanding the endocannabinoid system:** Studying the metabolism of THC and the formation of 11-OH-THC provides insights into the **function of the endocannabinoid system**, a critical regulatory network in the body.

**It's important to note:**

* 11-OH-THC is not found in the cannabis plant itself; it's only produced after THC is metabolized in the body.
* The exact effects of 11-OH-THC can vary depending on individual factors, such as metabolism, genetics, and tolerance.
* More research is needed to fully understand the long-term effects and potential risks of 11-OH-THC.

Overall, 11-OH-THC is an important compound to understand for both the research and medical communities, as it plays a significant role in the effects of cannabis and its potential therapeutic applications.

11-hydroxy-delta(9)-tetrahydrocannabinol: metabolite of marijuana; structure; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

11-hydroxy-Delta(9)-tetrahydrocannabinol : A phytocannabinoid that is Delta(9)-tetrahydrocannabinol in which the methyl group at C-11 has been hydroxylated . Major metabolite of Delta(9)-tetrahydrocannabinol. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID644022
CHEMBL ID3229459
CHEBI ID77270
SCHEMBL ID20763968
MeSH IDM0041623

Synonyms (56)

Synonym
brn 4259929
11-hydroxy-delta(9)-tetrahydrocannabinol
6h-dibenzo(b,d)pyran-9-methanol, 6a,7,8,10a-tetrahydro-6,6-dimethyl-1-hydroxy-3-pentyl-, (6ar-trans)-
PDSP2_000207
7-hydroxy-delta(sup 1)tetrahydrocannabinol
11-hydroxy-delta9-tetrahydrocannabinol
(-)-7-hydroxy-delta1-tetrahydrocannabinol
(-)-11-hydroxy-delta9-thc
36557-05-8
11-hydroxy-delta9-thc
6h-dibenzo[b,d]pyran-9-methanol, 6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-, (6ar-trans)-
7-hydroxy-delta1-tetrahydrocannabinol
11-hydroxy-delta(sup 9)tetrahydrocannabinol
11-hydroxytetrahydrocannabinol
11-oh-thc
(6ar,10ar)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
11-hydroxy-delta(9)-thc
7-hydroxy-delta(1)-tetrahydrocannabinol
11-hydroxy-delta(9)-tetrahydrocannabinol, (trans)-isomer
11-hydroxy-delta(9)-tetrahydrocannabinol, (6ar-trans)-isomer
bdbm84909
thc, 11-oh-delta 9
9vy04n5slb ,
unii-9vy04n5slb
(6ar,10ar)-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6h-dibenzo[b,d]pyran-9-methanol
(-)-11-hydroxy-delta(9)-thc
chebi:77270 ,
EPITOPE ID:224558
(-)-11-hydroxy-delta(9)-tetrahydrocannabinol
6h-dibenzo(b,d)pyran-9-methanol, 6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-, (6ar,10ar)-
11-hydroxy-.delta.9-thc
11-hydroxy-delta-9-tetrahydrocannabinol
11-hydroxy-.delta.9-tetrahydrocannabinol
(-)-11-hydroxy-.delta.9-thc
CHEMBL3229459
(6ar,10ar)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6h-benzo[c]chromen-1-ol
l-11-hydroxy-delta-9-thc
6h-dibenzo(b,d)pyran-9-methanol, 6a,7,8,10a-tetrahydro-6,6-dimethyl-1-hydroxy-3-pentyl-,(6ar-trans)-
7-hydroxy-.delta.1-tetrahydrocannabinol
9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6h-benzo[c]chromen-1-ol-, (6ar-trans)-
YCBKSSAWEUDACY-IAGOWNOFSA-N
11-hydroxy-.delta.-9-tetrahydrocannabinol
DTXSID50190061
(6ar,10ar)-rel-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6h-dibenzo[b,d]pyran-9-methanol; trans-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6h-dibenzo[b,d]pyran-9-methanol; (+/-)-11-hydroxy-?9-tetrahydrocannabinol; (+/-)-11-hydroxy-?
trans-11-hydroxy-delta9-thc ((6ars,10ars)-11-hydroxy-delta9-tetrahydrocannabinol) 0.1 mg/ml in methanol
34675-49-5
trans-11-hydroxy-delta9-thc ((6ars,10ars)-11-hydroxy-delta9-tetrahydrocannabinol) 1.0 mg/ml in methanol
(10ar)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6h-benzo[c]chromen-1-ol
Q63396108
SCHEMBL20763968
6h-dibenzo[b,d]pyran-9-methanol,6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-,(6ar,10ar)-rel-
(-)-11-?9-tetrahydro cannabinol-9-methanol
(+/-)-11-hydroxy-delta9-thc (crm)
(+/-)-11-hydroxy-?9-thc (crm)
d,l-11-hydroxy-delta-9-thc, 0.1mg/ml in methanol
d,l-11-hydroxy-delta-9-thc, 1mg/ml in methanol

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" No plasma pharmacokinetic data after repeated oral THC administration are available."( Delta9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC plasma pharmacokinetics during and after continuous high-dose oral THC.
Darwin, WD; Goodwin, RS; Gorelick, DA; Huestis, MA; Karschner, EL; Kelly, DL; Lowe, RH; Schwilke, EW; Schwope, DM, 2009
)
0.35
" There are indications that CBD modulates THC's effects, but it is unclear if this is due to a pharmacokinetic and/or pharmacodynamic interaction."( Plasma cannabinoid pharmacokinetics following controlled oral delta9-tetrahydrocannabinol and oromucosal cannabis extract administration.
Darwin, WD; Goodwin, RS; Huestis, MA; Karschner, EL; Wright, S, 2011
)
0.37
"These data suggest that CBD modulation of THC's effects is not due to a pharmacokinetic interaction at these therapeutic doses."( Plasma cannabinoid pharmacokinetics following controlled oral delta9-tetrahydrocannabinol and oromucosal cannabis extract administration.
Darwin, WD; Goodwin, RS; Huestis, MA; Karschner, EL; Wright, S, 2011
)
0.37
" We therefore sought to characterize the pharmacokinetics of THC and its major metabolites 11-hydroxy-delta-9-tetrahydrocannabinol (THC-OH) and 11-nor-9-carboxy-delta-9-tetrahydrocannabinol (THC-COOH) in healthy volunteers with known CYP2C9 status by non-compartmental analysis (NCA), compartmental modeling (CM) and minimal physiologically based pharmacokinetic (mPBPK) modeling."( Minimal Physiologically Based Pharmacokinetic Model of Intravenously and Orally Administered Delta-9-Tetrahydrocannabinol in Healthy Volunteers.
Bernhard, W; Greif, R; Kleine-Brueggeney, M; Theiler, L; Wolowich, WR, 2019
)
0.51

Bioavailability

ExcerptReferenceRelevance
" Relative bioavailability was calculated to determine the relative rate and extent of THC absorption; 5 and 15 mg oral THC bioavailability was 92."( Plasma cannabinoid pharmacokinetics following controlled oral delta9-tetrahydrocannabinol and oromucosal cannabis extract administration.
Darwin, WD; Goodwin, RS; Huestis, MA; Karschner, EL; Wright, S, 2011
)
0.37

Dosage Studied

ExcerptRelevanceReference
" This age-related difference was seen in the dose-response studies as well as in the studies with varying cell numbers in culture."( Age-associated differences in cannabinoid-induced suppression of murine spleen, lymph node and thymus cell blastogenic responses.
Friedman, H; Klein, TW; Newton, C; Pross, S, 1987
)
0.27
" Plasma specimens were collected during and after each dosing condition."( Delta(9)-tetrahydrocannabinol, 11-hydroxy-delta(9)-tetrahydrocannabinol and 11-nor-9-carboxy-delta(9)-tetrahydrocannabinol in human plasma after controlled oral administration of cannabinoids.
Barnes, A; Goodwin, RS; Gustafson, RA; Huestis, MA; Moolchan, ET; Nebro, W, 2006
)
0.33
"Nine cannabis smokers completed all 5 dosing sessions."( Plasma cannabinoid pharmacokinetics following controlled oral delta9-tetrahydrocannabinol and oromucosal cannabis extract administration.
Darwin, WD; Goodwin, RS; Huestis, MA; Karschner, EL; Wright, S, 2011
)
0.37
" Blood samples from orally dosed (10, 25 and 50 mg) THC brownies were added to validate the model."( Minimal Physiologically Based Pharmacokinetic Model of Intravenously and Orally Administered Delta-9-Tetrahydrocannabinol in Healthy Volunteers.
Bernhard, W; Greif, R; Kleine-Brueggeney, M; Theiler, L; Wolowich, WR, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human xenobiotic metaboliteAny human metabolite produced by metabolism of a xenobiotic compound in humans.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
phytocannabinoidA class of cannabinoid which are C21 terpenophenolic compounds isolated primarily from Cannabis sativa.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1133175Molar volume, Vm of the compound at zero temperature1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Molar volume relationships and the specific inhibition of a synaptosomal enzyme by psychoactive cannabinoids.
AID1124427Analgesic activity in sc dosed mouse by hot-plate method1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Some 11-substituted tetrahydrocannabinols. Synthesis and comparison with the potent cannabinoid metabolites 11-hydroxytetrahydrocannabinols.
AID1124418Induction of overt behavior in dog at 0.10 mg/kg, iv1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Some 11-substituted tetrahydrocannabinols. Synthesis and comparison with the potent cannabinoid metabolites 11-hydroxytetrahydrocannabinols.
AID1124417Induction of overt behavior in dog at 0.05 mg/kg, iv1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Some 11-substituted tetrahydrocannabinols. Synthesis and comparison with the potent cannabinoid metabolites 11-hydroxytetrahydrocannabinols.
AID1133174Antihemolytic potency against hypotonic lysis-induced erythrocytes (unknown origin) assessed as stabilization1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Molar volume relationships and the specific inhibition of a synaptosomal enzyme by psychoactive cannabinoids.
AID1133173Inhibition of mouse brain synaptosomal Lysophosphatidylcholine acyltransferase using substrate [32P]lysophosphatidylcholine and oleoyl-CoA1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Molar volume relationships and the specific inhibition of a synaptosomal enzyme by psychoactive cannabinoids.
AID1124416Induction of overt behavior in dog at 0.01 mg/kg, iv1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Some 11-substituted tetrahydrocannabinols. Synthesis and comparison with the potent cannabinoid metabolites 11-hydroxytetrahydrocannabinols.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (77)

TimeframeStudies, This Drug (%)All Drugs %
pre-199015 (19.48)18.7374
1990's12 (15.58)18.2507
2000's19 (24.68)29.6817
2010's28 (36.36)24.3611
2020's3 (3.90)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials12 (13.48%)5.53%
Reviews2 (2.25%)6.00%
Case Studies2 (2.25%)4.05%
Observational0 (0.00%)0.25%
Other73 (82.02%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]