Compounds > 8-hydroxy-delta(9)-tetrahydrocannabinol
Page last updated: 2024-12-08

8-hydroxy-delta(9)-tetrahydrocannabinol

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Description

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

Cross-References

ID SourceID
PubMed CID169652
CHEMBL ID3586105
SCHEMBL ID23043730
MeSH IDM0104971

Synonyms (22)

Synonym
34984-78-6
671a0k1fqe ,
8 beta-hydroxy-delta(9)-tetrahyrocannabinol
8-hydroxy-delta(9)-tetrahydrocannabinol
8alpha-hydroxy-delta (9)-thc
8-ohthc
8beta-hydroxy-delta (9)-thc
6h-dibenzo(b,d)pyran-1,8-diol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6ar-(6aalpha,8alpha,10abeta))-
unii-671a0k1fqe
thc, 8 beta-oh
bdbm84880
CHEMBL3586105
DTXSID10188525
(-)-8.beta.-hydroxy-.delta.9-tetrahydrocannabinol
8.beta.-hydroxy-.delta.9-thc
6h-dibenzo(b,d)pyran-1,8-diol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6ar,8r,10ar)-
8.beta.-hydroxy-.delta.9-tetrahydrocannabinol
8?-hydroxy-?9-tetrahydro cannabinol
SCHEMBL23043730
(8r)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo(c)chromene-1,8-diol
6h-dibenzo(b,d)pyran-1,8-diol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6a.alpha.,8.alpha.,10a.beta.)-
PD167671
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 1Homo sapiens (human)Ki0.06500.00010.50779.6000AID1230030
Cannabinoid receptor 2 Homo sapiens (human)Ki0.08800.00000.415610.0000AID1230031
[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 (17)

Assay IDTitleYearJournalArticle
AID1230037Neurobehavioral effect on Swiss Webster mouse assessed as catalepsy latency time at 10 mg/kg, ip (Rvb = 2.1 +/- 0.60 secs) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230047Neurobehavioral effect on Swiss Webster mouse assessed as hot plate latency time at 40 mg/kg, ip (Rvb = 8.32 +/- 2.20 %) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230033Neurobehavioral effect on Swiss Webster mouse assessed as locomotor activity measured as total number of interruptions at 10 mg/kg, ip monitored for 30 mins (Rvb = 2091 +/- 209.3 No_unit) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230042Neurobehavioral effect on Swiss Webster mouse assessed as tail-flick latency time at 20 mg/kg, ip (Rvb = 0.84 +/- 3.58 %) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230051Neurobehavioral effect on Swiss Webster mouse assessed as decrease in rectal temperature at 40 mg/kg, ip (Rvb = 0.58 +/- 0.26 degC) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230039Neurobehavioral effect on Swiss Webster mouse assessed as catalepsy latency time at 40 mg/kg, ip (Rvb = 2.1 +/- 0.60 secs) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230050Neurobehavioral effect on Swiss Webster mouse assessed as decrease in rectal temperature at 20 mg/kg, ip (Rvb = 0.58 +/- 0.26 degC) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230035Neurobehavioral effect on Swiss Webster mouse assessed as locomotor activity measured as total number of interruptions at 40 mg/kg, ip monitored for 30 mins (Rvb = 2091 +/- 209.3 No_unit) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230046Neurobehavioral effect on Swiss Webster mouse assessed as hot plate latency time at 20 mg/kg, ip (Rvb = 8.32 +/- 2.20 %) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230034Neurobehavioral effect on Swiss Webster mouse assessed as locomotor activity measured as total number of interruptions at 20 mg/kg, ip monitored for 30 mins (Rvb = 2091 +/- 209.3 No_unit) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230030Displacement of [3H]CP55940 from full length human recombinant CB1 receptor expressed in HEK293 cells after 90 mins by scintillation counting analysis2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230043Neurobehavioral effect on Swiss Webster mouse assessed as tail-flick latency time at 40 mg/kg, ip (Rvb = 0.84 +/- 3.58 %) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230031Displacement of [3H]CP55940 from full length human recombinant CB2 receptor expressed in HEK293 cells after 90 mins by scintillation counting analysis2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230049Neurobehavioral effect on Swiss Webster mouse assessed as decrease in rectal temperature at 10 mg/kg, ip (Rvb = 0.58 +/- 0.26 degC) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230038Neurobehavioral effect on Swiss Webster mouse assessed as catalepsy latency time at 20 mg/kg, ip (Rvb = 2.1 +/- 0.60 secs) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230045Neurobehavioral effect on Swiss Webster mouse assessed as hot plate latency time at 10 mg/kg, ip (Rvb = 8.32 +/- 2.20 %) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
AID1230041Neurobehavioral effect on Swiss Webster mouse assessed as tail-flick latency time at 10 mg/kg, ip (Rvb = 0.84 +/- 3.58 %) by mouse tetrad assay2015Journal of natural products, Jun-26, Volume: 78, Issue:6
Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (50.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's2 (33.33)24.3611
2020's0 (0.00)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 (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phenytoin
[no description available]		1.9610imidazolidine-2,4-dioneanticonvulsant;
drug allergen;
sodium channel blocker;
teratogenic agent
1,2-dipalmitoylphosphatidylcholine
1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.		1.9710
dronabinol
Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.		4.3460benzochromene;
diterpenoid;
phytocannabinoid;
polyketide		cannabinoid receptor agonist;
epitope;
hallucinogen;
metabolite;
non-narcotic analgesic
8-bromo cyclic adenosine monophosphate
8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.		1.96103',5'-cyclic purine nucleotide;
adenyl ribonucleotide;
organobromine compound		antidepressant;
protein kinase agonist
11-hydroxy-delta(8)-tetrahydrocannabinol
11-hydroxy-delta(8)-tetrahydrocannabinol: metabolite of THC; RN given refers to cpd without isomeric designation		3.1610
delta-8-tetrahydrocannabinol
[no description available]		2.11101-benzopyran
cannabidiol
Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.		1.9610olefinic compound;
phytocannabinoid;
resorcinols		antimicrobial agent;
plant metabolite
11-hydroxy-delta(9)-tetrahydrocannabinol
11-hydroxy-delta(9)-tetrahydrocannabinol: metabolite of marijuana; structure; RN given refers to cpd without isomeric designation. 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.		2.3720phytocannabinoidhuman xenobiotic metabolite
11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid
11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid: RN given refers to cpd without isomeric designation; a major acidic metabolite of tetrahydrocannabinol in human urine		3.16101-benzopyran
ConditionIndicatedRelationship StrengthStudiesTrials
Cannabis Abuse
[description not available]		02.9810
Marijuana Abuse
Use of marijuana associated with abnormal psychological, social, and or occupational functioning.		02.9810
Aura
[description not available]		01.9610
Epilepsy
A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)		01.9610