Page last updated: 2024-12-07

1,1-dimethylheptyl-11-hydroxytetrahydrocannabinol

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Description

You're likely referring to **11-hydroxy-Δ⁸-tetrahydrocannabinol**, also known as **11-hydroxy-THC**, which is a major metabolite of **Δ⁸-tetrahydrocannabinol (Δ⁸-THC)**. It's not 1,1-dimethylheptyl-11-hydroxytetrahydrocannabinol.

Here's why it's important for research:

**1. Psychoactive Effects:** 11-hydroxy-THC is actually **more potent** than Δ⁸-THC in terms of producing psychoactive effects. This means it plays a significant role in the high experienced after consuming cannabis.

**2. Metabolic Pathway:** Understanding the conversion of Δ⁸-THC to 11-hydroxy-THC is crucial for studying the pharmacokinetics of cannabis use. This knowledge helps researchers understand how the body processes and eliminates THC.

**3. Therapeutic Potential:** 11-hydroxy-THC has been suggested to possess different therapeutic properties than Δ⁸-THC. Research is ongoing to explore its potential in managing conditions like pain, nausea, and anxiety.

**4. Drug Testing:** 11-hydroxy-THC can be detected in urine and blood samples for longer periods than Δ⁸-THC, making it a valuable marker for drug testing.

**5. Understanding Cannabis Effects:** Researching 11-hydroxy-THC helps us understand the full spectrum of effects cannabis has on the human body, including both positive and negative impacts.

**Important Notes:**

* The nomenclature you provided (1,1-dimethylheptyl-11-hydroxytetrahydrocannabinol) is not a recognized chemical name.
* The 11 in 11-hydroxy-THC refers to the position of the hydroxyl group (OH) on the THC molecule.
* Δ⁸-THC is a specific isomer of THC, and its metabolism differs slightly from Δ⁹-THC (the more common form of THC).

If you're interested in learning more about cannabis research, it's crucial to rely on reputable sources and scientific publications.

HU 211: structure given in first source; HU 211 is active & HU 210 is inactive as canibinoids; functional N-methyl-D-aspartate receptor blocker; RN given is for (6aS-trans)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID107778
CHEMBL ID334533
SCHEMBL ID1649687
MeSH IDM0171814

Synonyms (42)

Synonym
PDSP2_000937
hu-211
11-hydroxymethyl-delta(8)-tetrahydrocannabinol-dimethylheptyl
1,1-dimethylheptyl-7-hydroxy-delta(6)-tetrahydrocannabinol
11-hydroxy-delta-8-dmh-thc
hu 211
5'(1,1-dimethylheptyl)-7-hydroxyhexahydrocannabinol
11-hydroxy-delta(8)-tetrahydrocannabinol-dimethylheptyl
sinnabidiol
1,1-dimethylheptyl-11-hydroxytetrahydrocannabinol
prs 211007-000
11-oh-delta(8)-thc-dmh
7-hydroxy-delta-6-tetrahydrocannabinoldimethylheptyl
dexanabinol
6h-dibenzo(b,d)pyran-9-methanol, 3-(1,1-dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-, (6as-trans)-
prs-211007
CHEMBL334533 ,
pa-50211
sinnabidol
prs-211007-000
bdbm50067498
(6as,10as)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydro-6h-benzo[c]chromen-1-ol
(6as,7s)-3-(1,1-dimethyl-heptyl)-9-hydroxymethyl-6,6-dimethyl-6a,7,10,10a-tetrahydro-6h-benzo[c]chromen-1-ol
(6as,10as)-3-(1,1-dimethyl-heptyl)-9-hydroxymethyl-6,6-dimethyl-6a,7,10,10a-tetrahydro-6h-benzo[c]chromen-1-ol
(6as,10as)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
112924-45-5
AKOS015967265
unii-r6vt8u5372
r6vt8u5372 ,
6h-dibenzo(b,d)pyran-9-methanol, 3-(1,1-dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-, (6as,10as)-
dexanabinol [mi]
(+)-hu-210
sinnabidol [who-dd]
(6as,10as)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)- 6a,7,10,10a-tetrahydrobenzo(c)chromen-1-ol
SCHEMBL1649687
(6as,10as)-3-(1,1-dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6h-dibenzo[b,d]pyran-9-methanol
DTXSID40150235
6h-dibenzo[b,d]pyran-9-methanol, 3-(1,1-dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-, (6as,10as)-
DB06444
HY-106387
Q962504
CS-0025698

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Dexanabinol was not associated with hepatic, renal, or cardiac toxic effects."( Efficacy and safety of dexanabinol in severe traumatic brain injury: results of a phase III randomised, placebo-controlled, clinical trial.
Henney, H; Kassem, N; Knoller, N; Legrand, V; Maas, AI; Mangelus, M; Muizelaar, JP; Murray, G; Stocchetti, N, 2006
)
0.33

Pharmacokinetics

ExcerptReferenceRelevance
" The elimination of dexanabinol was best fitted to a 3-compartment model with a rapid distribution half-life (< 5 min), an intermediate phase half-life of approximately 90 min, and a slow terminal elimination half-life (approximately 9 h)."( Clinical pharmacokinetics of escalating i.v. doses of dexanabinol (HU-211), a neuroprotectant agent, in normal volunteers.
Amselem, S; Biegon, A; Brewster, ME; Foltz, RL; Griffith, W; Pop, E; Reuschel, S, 1997
)
0.3
" Beside pharmacokinetic differences, these data therefore denote distinct pharmacodynamic profiles for HU 210 and CP 55,940."( Revisiting the complex influences of cannabinoids on motor functions unravels pharmacodynamic differences between cannabinoid agonists.
Bosier, B; Hermans, E; Lambert, DM; Michotte, Y; Sarre, S; Smolders, I, 2010
)
0.36

Bioavailability

ExcerptReferenceRelevance
"The aim of this article was to investigate the role of intestinal lymphatic transport in the oral bioavailability of two structurally similar synthetic lipophilic cannabinoids: dexanabinol and PRS-211,220."( Different impacts of intestinal lymphatic transport on the oral bioavailability of structurally similar synthetic lipophilic cannabinoids: dexanabinol and PRS-211,220.
Amselem, S; Gershkovich, P; Hoffman, A; Qadri, B; Yacovan, A, 2007
)
0.34

Dosage Studied

ExcerptRelevanceReference
"The purpose of the present study was to examine the dose-response relationship and the therapeutic time window for the synthetic nonpsychotropic cannabinoid (HU-211) as a neuroprotective agent in transient, severe forebrain ischemia in the rat."( HU-211, a nonpsychotropic cannabinoid, improves neurological signs and reduces brain damage after severe forebrain ischemia in rats.
Adamchik, J; Bar-Joseph, A; Belayev, L; Biegon, A, 1995
)
0.29
" After dose-response and therapeutic time window-finding experiments, the rats were injected with HU-210 (45 microg/kg IV) or vehicle 1 hour after PMCAO."( Drug-induced hypothermia reduces ischemic damage: effects of the cannabinoid HU-210.
Gai, N; Leker, RR; Mechoulam, R; Ovadia, H, 2003
)
0.32
" Moreover, dose-response curves of the agonists showed that mu and CB1 receptors mediating inhibition of [3H]glutamate release display a non-additive interaction, whereas these receptors synergistically interact regarding their inhibitory control of [3H]GABA release."( Interactions between CB1 cannabinoid and mu opioid receptors mediating inhibition of neurotransmitter release in rat nucleus accumbens core.
De Vries, TJ; Hogenboom, F; Schoffelmeer, AN; Wardeh, G, 2006
)
0.33
" Repeated injections of morphine caused a rightward shift in the morphine dose-response curve on Day 3 (i."( Repeated cannabinoid injections into the rat periaqueductal gray enhance subsequent morphine antinociception.
Maher, L; Morgan, MM; Wilson, AR, 2008
)
0.35
" Drug deliveries calculated as percent vehicle followed a prototypical inverted-U shaped dose-response curve for cannabinoids and heroin except for THC and JWH-018 (in males)."( Self-administration of inhaled delta-9-tetrahydrocannabinol and synthetic cannabinoids in non-human primates.
Cooper, ZD; Evans, SM; Foltin, RW, 2021
)
0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki1.99000.00020.566510.0000AID1127488
Cannabinoid receptor 1Homo sapiens (human)Ki0.01880.00010.50779.6000AID238849; AID283041
Cannabinoid receptor 2 Homo sapiens (human)Ki0.07510.00000.415610.0000AID282919; AID289136
Cannabinoid receptor 2Rattus norvegicus (Norway rat)Ki10.00000.02000.22060.9120AID1127489
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 1Homo sapiens (human)EC50 (µMol)0.00060.00010.12752.2400AID283043
Cannabinoid receptor 2 Homo sapiens (human)EC50 (µMol)0.00030.00030.15173.2800AID282754
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
positive regulation of acute inflammatory response to antigenic stimulusCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
spermatogenesisCannabinoid receptor 1Homo sapiens (human)
axonal fasciculationCannabinoid receptor 1Homo sapiens (human)
response to nutrientCannabinoid receptor 1Homo sapiens (human)
memoryCannabinoid receptor 1Homo sapiens (human)
positive regulation of neuron projection developmentCannabinoid receptor 1Homo sapiens (human)
negative regulation of serotonin secretionCannabinoid receptor 1Homo sapiens (human)
positive regulation of fever generationCannabinoid receptor 1Homo sapiens (human)
negative regulation of fatty acid beta-oxidationCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, GABAergicCannabinoid receptor 1Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 1Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 1Homo sapiens (human)
negative regulation of dopamine secretionCannabinoid receptor 1Homo sapiens (human)
response to nicotineCannabinoid receptor 1Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 1Homo sapiens (human)
response to cocaineCannabinoid receptor 1Homo sapiens (human)
glucose homeostasisCannabinoid receptor 1Homo sapiens (human)
positive regulation of apoptotic processCannabinoid receptor 1Homo sapiens (human)
response to ethanolCannabinoid receptor 1Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 1Homo sapiens (human)
negative regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
positive regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
regulation of insulin secretionCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicCannabinoid receptor 1Homo sapiens (human)
maternal process involved in female pregnancyCannabinoid receptor 1Homo sapiens (human)
regulation of feeding behaviorCannabinoid receptor 1Homo sapiens (human)
regulation of penile erectionCannabinoid receptor 1Homo sapiens (human)
retrograde trans-synaptic signaling by endocannabinoidCannabinoid receptor 1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationCannabinoid receptor 1Homo sapiens (human)
trans-synaptic signaling by endocannabinoid, modulating synaptic transmissionCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 1Homo sapiens (human)
response to amphetamineCannabinoid receptor 2 Homo sapiens (human)
inflammatory responseCannabinoid receptor 2 Homo sapiens (human)
immune responseCannabinoid receptor 2 Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 2 Homo sapiens (human)
leukocyte chemotaxisCannabinoid receptor 2 Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicCannabinoid receptor 2 Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 2 Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 2 Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 2 Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 2 Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
cannabinoid receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 1Homo sapiens (human)
identical protein bindingCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 2 Homo sapiens (human)
cannabinoid receptor activityCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
mitochondrial outer membraneCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
actin cytoskeletonCannabinoid receptor 1Homo sapiens (human)
growth coneCannabinoid receptor 1Homo sapiens (human)
presynaptic membraneCannabinoid receptor 1Homo sapiens (human)
membrane raftCannabinoid receptor 1Homo sapiens (human)
glutamatergic synapseCannabinoid receptor 1Homo sapiens (human)
GABA-ergic synapseCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
cytoplasmCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
dendriteCannabinoid receptor 2 Homo sapiens (human)
extrinsic component of cytoplasmic side of plasma membraneCannabinoid receptor 2 Homo sapiens (human)
perikaryonCannabinoid receptor 2 Homo sapiens (human)
endoplasmic reticulumCannabinoid receptor 2 Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
cytoplasmCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1127488Displacement of [3H]-CP55940 from rat CB1 receptor by liquid scintillation spectrometry2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID289136Displacement of [3H]CP-55940 from human CB2 receptor expressed in HEK cells2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Design, synthesis, binding, and molecular modeling studies of new potent ligands of cannabinoid receptors.
AID282754Agonist activity at human CB2 receptor transfected in CHO cells by [35]GTPgamma binding assay2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Virtual screening of novel CB2 ligands using a comparative model of the human cannabinoid CB2 receptor.
AID283043Activity at human CB1 receptor by [35S]GTP-gamma-S binding stimulation assay2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: new templates among the CB1 cannabinoid receptor inverse agonists.
AID49666Displacement of [3H]CP-55940 binding to Cannabinoid receptor 1 in rat brain membranes1998Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22
Derivation of a pharmacophore model for anandamide using constrained conformational searching and comparative molecular field analysis.
AID283040Displacement of [3H]SR141716A from human CB1 receptor expressed in CHO cells at 10 uM2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: new templates among the CB1 cannabinoid receptor inverse agonists.
AID283042Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO cells at 10 uM2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: new templates among the CB1 cannabinoid receptor inverse agonists.
AID283041Displacement of [3H]SR141716A from human CB1 receptor expressed in CHO cells2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: new templates among the CB1 cannabinoid receptor inverse agonists.
AID282919Displacement of [3H]CP-55940 from human CB2 receptor expressed in COS cells2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Design, synthesis, and binding studies of new potent ligands of cannabinoid receptors.
AID1127489Displacement of [3H]-CP55940 from rat CB2 receptor by liquid scintillation spectrometry2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID1127492Selectivity ratio of Ki for rat CB1 receptor to Ki for rat CB2 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID283044Activity at human CB1 receptor by [35S]GTP-gamma-S binding stimulation assay at 10 uM relative to basal level2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: new templates among the CB1 cannabinoid receptor inverse agonists.
AID238849Inhibition of [3H]SR-141,716A binding to human CB1 receptor expressed in CHO cells2005Journal of medicinal chemistry, Apr-07, Volume: 48, Issue:7
Substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one as CB1 cannabinoid receptor ligands: synthesis and pharmacological evaluation.
AID243419Increase in [35S]GTP-gamma-S, binding to human Cannabinoid receptor 1 expressed in CHO cells at 10 uM 2005Journal of medicinal chemistry, Apr-07, Volume: 48, Issue:7
Substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one as CB1 cannabinoid receptor ligands: synthesis and pharmacological evaluation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (332)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (0.90)18.7374
1990's59 (17.77)18.2507
2000's182 (54.82)29.6817
2010's82 (24.70)24.3611
2020's6 (1.81)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.30

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.30 (24.57)
Research Supply Index5.86 (2.92)
Research Growth Index6.15 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (1.46%)5.53%
Reviews13 (3.79%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other325 (94.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]