Compounds > 11-hydroxy-delta(9)-tetrahydrocannabinol
Page last updated: 2024-09-22

11-hydroxy-delta(9)-tetrahydrocannabinol

Description

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

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]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
delta-8-tetrahydrocannabinol[no description available]medium201-benzopyran
morphine chloride[no description available]medium10hydrochloride
1-octanol[no description available]medium10octanol;
primary alcohol		antifungal agent;
bacterial metabolite;
fuel additive;
kairomone;
plant metabolite
cannabinol[no description available]medium60dibenzopyran
chlorpromazine[no description available]medium10organochlorine compound;
phenothiazines;
tertiary amine		anticoronaviral agent;
antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
phenothiazine antipsychotic drug
4-chlorophenol[no description available]medium10monochlorophenol
2-chlorophenol[no description available]medium102-halophenol;
monochlorophenol
n-decyl alcohol[no description available]medium10decanol;
primary alcohol		metabolite;
pheromone;
protic solvent
dodecanol[no description available]medium10dodecanol;
primary alcohol		bacterial metabolite;
cosmetic;
insect attractant;
insecticide;
pheromone;
plant metabolite
synhexyl[no description available]medium10
1-nonanol[no description available]medium10nonanol;
primary alcohol		antifungal agent;
flavouring agent;
plant metabolite;
volatile oil component
dronabinol[no description available]medium880benzochromene;
diterpenoid;
phytocannabinoid;
polyketide		cannabinoid receptor agonist;
epitope;
hallucinogen;
metabolite;
non-narcotic analgesic
dronabinol[no description available]medium889benzochromene;
diterpenoid;
phytocannabinoid;
polyketide		cannabinoid receptor agonist;
epitope;
hallucinogen;
metabolite;
non-narcotic analgesic
beta-thujone[no description available]medium10alpha-thujone
retinol[no description available]medium10retinol;
vitamin A		human metabolite;
mouse metabolite;
plant metabolite
cannabigerol[no description available]medium10phytocannabinoid;
resorcinols		anti-inflammatory agent;
antibacterial agent;
antioxidant;
appetite enhancer;
cannabinoid receptor agonist;
neuroprotective agent;
plant metabolite
cannabidiol[no description available]medium100olefinic compound;
phytocannabinoid;
resorcinols		antimicrobial agent;
plant metabolite
cannabidiol[no description available]medium101olefinic compound;
phytocannabinoid;
resorcinols		antimicrobial agent;
plant metabolite
delta(9)-tetrahydrocannabinolic acid[no description available]medium90benzochromene;
diterpenoid;
hydroxy monocarboxylic acid;
phytocannabinoid;
polyketide		anti-inflammatory agent;
biomarker;
metabolite;
neuroprotective agent
delta(9)-tetrahydrocannabinolic acid[no description available]medium91benzochromene;
diterpenoid;
hydroxy monocarboxylic acid;
phytocannabinoid;
polyketide		anti-inflammatory agent;
biomarker;
metabolite;
neuroprotective agent
delta(9-11)-tetrahydrocannabinol[no description available]medium20
11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid[no description available]medium4571-benzopyran
palmitic acid[no description available]medium10long-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
Daphnia magna metabolite;
EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor;
plant metabolite
raclopride[no description available]medium11salicylamides
gw 1000[no description available]medium11
piperidines[no description available]medium11
sr141716[no description available]medium11amidopiperidine;
carbohydrazide;
dichlorobenzene;
monochlorobenzenes;
pyrazoles		anti-obesity agent;
appetite depressant;
CB1 receptor antagonist
glyceryl 2-arachidonate[no description available]medium102-acylglycerol 20:4;
endocannabinoid		human metabolite
1-propanol[no description available]medium10propan-1-ols;
short-chain primary fatty alcohol		metabolite;
protic solvent
nordazepam[no description available]medium101,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
GABA modulator;
human metabolite;
sedative
11-nor-delta(8)-tetrahydrocannabinol-9-carboxylic acid[no description available]medium20
sodium hydroxide[no description available]medium11alkali metal hydroxide
proadifen[no description available]medium10diarylmethane
2,4-dichloro-6-phenylphenoxyethylamine[no description available]medium10
phenytoin[no description available]medium10imidazolidine-2,4-dioneanticonvulsant;
drug allergen;
sodium channel blocker;
teratogenic agent
8-hydroxy-delta(9)-tetrahydrocannabinol[no description available]medium20
naltrexone[no description available]medium10cyclopropanes;
morphinane-like compound;
organic heteropentacyclic compound		antidote to opioid poisoning;
central nervous system depressant;
environmental contaminant;
mu-opioid receptor antagonist;
xenobiotic
boranes[no description available]medium10boranes;
mononuclear parent hydride
trifluoroacetic acid[no description available]medium10fluoroalkanoic acidhuman xenobiotic metabolite;
NMR chemical shift reference compound;
reagent
boron trifluoride[no description available]medium10boron fluorideNMR chemical shift reference compound
methylene chloride[no description available]medium10chloromethanes;
volatile organic compound		carcinogenic agent;
polar aprotic solvent;
refrigerant
11-oxo-delta(8)-tetrahydrocannabinol[no description available]medium10
tetradecanoylphorbol acetate[no description available]medium10acetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester		antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator
sq-23377[no description available]medium10cyclic ether;
enol;
polyunsaturated fatty acid;
very long-chain fatty acid		calcium ionophore;
metabolite
indomethacin[no description available]medium10aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
11-hydroxy-delta(8)-tetrahydrocannabinol[no description available]medium10
concanavalin a[no description available]medium20
nantradol[no description available]medium10
8-bromo cyclic adenosine monophosphate[no description available]medium103',5'-cyclic purine nucleotide;
adenyl ribonucleotide;
organobromine compound		antidepressant;
protein kinase agonist
2,3-dihydroxybenzoic acid[no description available]low00dihydroxybenzoic acidhuman xenobiotic metabolite;
plant metabolite
2,5-dichlorophenol[no description available]low00dichlorophenolhuman xenobiotic metabolite
protocatechuic acid[no description available]low00catechols;
dihydroxybenzoic acid		antineoplastic agent;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor;
human xenobiotic metabolite;
plant metabolite
dihydro-3-coumaric acid[no description available]low00monocarboxylic acidEscherichia coli metabolite;
human xenobiotic metabolite
2-(3-pyridine)acetic acid[no description available]low00monocarboxylic acid;
pyridines		human xenobiotic metabolite
adipic acid[no description available]low00alpha,omega-dicarboxylic acid;
dicarboxylic fatty acid		food acidity regulator;
human xenobiotic metabolite
benzoic acid[no description available]low00benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
2-cresol[no description available]low00cresolhuman xenobiotic metabolite
3-cresol[no description available]low00cresolhuman xenobiotic metabolite
gallic acid[no description available]low00trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite
diethyl phosphate[no description available]low00dialkyl phosphatehuman xenobiotic metabolite;
mouse metabolite
o,o-diethyl phosphorothionate[no description available]low00organic thiophosphatehuman xenobiotic metabolite;
mouse metabolite
hydroquinone[no description available]low00benzenediol;
hydroquinones		antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent
melilotic acid[no description available]low00monocarboxylic acid;
phenols		bacterial xenobiotic metabolite;
fungal xenobiotic metabolite;
human xenobiotic metabolite;
plant metabolite
norepinephrine, (+,-)-isomer[no description available]low00catecholaminehuman xenobiotic metabolite
4-nitrophenol[no description available]low004-nitrophenolshuman xenobiotic metabolite;
mouse metabolite
pentachlorophenol[no description available]low00aromatic fungicide;
chlorophenol;
organochlorine pesticide;
pentachlorobenzenes		human xenobiotic metabolite
phenol[no description available]low00phenolsantiseptic drug;
disinfectant;
human xenobiotic metabolite;
mouse metabolite
phthalic acid[no description available]low00benzenedicarboxylic acidhuman xenobiotic metabolite
propylene glycol[no description available]low00glycol;
propane-1,2-diols		allergen;
human xenobiotic metabolite;
mouse metabolite;
protic solvent
trimethylamine[no description available]low00methylamines;
tertiary amine		Escherichia coli metabolite;
human xenobiotic metabolite
mandelic acid[no description available]low002-hydroxy monocarboxylic acid;
benzenes		antibacterial agent;
human xenobiotic metabolite
dichlorodiphenyl dichloroethylene[no description available]low00chlorophenylethylene;
monochlorobenzenes		human xenobiotic metabolite;
persistent organic pollutant
quinone[no description available]low001,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
1,7-dimethylxanthine[no description available]low00dimethylxanthinecentral nervous system stimulant;
human blood serum metabolite;
human xenobiotic metabolite;
mouse metabolite
psilocin[no description available]low00hydroxyindoles;
phenols;
tertiary amino compound;
tryptamine alkaloid		drug metabolite;
fungal metabolite;
hallucinogen;
human xenobiotic metabolite;
serotonergic agonist
estriol[no description available]low0016alpha-hydroxy steroid;
17beta-hydroxy steroid;
3-hydroxy steroid		estrogen;
human metabolite;
human xenobiotic metabolite;
mouse metabolite
phenylalanine[no description available]low00amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
tert-butyl alcohol[no description available]low00tertiary alcoholhuman xenobiotic metabolite
2-furoic acid[no description available]low00furoic acidbacterial xenobiotic metabolite;
human xenobiotic metabolite;
inhibitor;
plant metabolite;
Saccharomyces cerevisiae metabolite
1-naphthol[no description available]low00naphtholgenotoxin;
human xenobiotic metabolite
2-phenylbutyric acid[no description available]low00benzenes;
monocarboxylic acid		human xenobiotic metabolite
benzohydrol[no description available]low00benzyl alcohols;
secondary alcohol		bacterial xenobiotic metabolite;
human urinary metabolite;
human xenobiotic metabolite;
rat metabolite
(3,4-dimethoxyphenyl)acetic acid[no description available]low00dimethoxybenzene;
phenylacetic acids		human urinary metabolite;
human xenobiotic metabolite
styrene oxide[no description available]low00epoxidehuman xenobiotic metabolite
3-toluic acid[no description available]low00methylbenzoic acidhuman xenobiotic metabolite
gamma-terpinene[no description available]low00cyclohexadiene;
monoterpene		antioxidant;
human xenobiotic metabolite;
plant metabolite;
volatile oil component
cyclamic acid[no description available]low00sulfamic acidsenvironmental contaminant;
human xenobiotic metabolite
4-bromophenol[no description available]low00bromophenolhuman urinary metabolite;
human xenobiotic metabolite;
marine metabolite;
mouse metabolite;
persistent organic pollutant;
rat metabolite
acrolein[no description available]low00enalherbicide;
human xenobiotic metabolite;
toxin
gamma-valerolactone[no description available]low00butan-4-olideflavouring agent;
human xenobiotic metabolite
cyclohexanone[no description available]low00cyclohexanoneshuman xenobiotic metabolite
2,5-hexanedione[no description available]low00diketone;
methyl ketone		human xenobiotic metabolite;
neurotoxin
diethanolamine[no description available]low00ethanolamineshuman xenobiotic metabolite
3,4,5-trimethoxybenzoic acid[no description available]low00benzoic acids;
methoxybenzenes		human urinary metabolite;
human xenobiotic metabolite;
plant metabolite
3-tert-butyl-4-hydroxyanisole[no description available]low00aromatic ether;
phenols		antioxidant;
human xenobiotic metabolite
1-naphthylamine[no description available]low00naphthylaminehuman xenobiotic metabolite
2-naphthol[no description available]low00naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger
salicylurate[no description available]low00N-acylglycine;
secondary carboxamide		human xenobiotic metabolite;
uremic toxin
indole-3-carbaldehyde[no description available]low00heteroarenecarbaldehyde;
indole alkaloid;
indoles		bacterial metabolite;
human xenobiotic metabolite;
marine metabolite;
plant metabolite
hydratropic acid[no description available]low002-arylpropionic acidhuman xenobiotic metabolite
tropic acid[no description available]low003-hydroxy monocarboxylic acidhuman xenobiotic metabolite
2-hydroxyisobutyric acid[no description available]low002-hydroxy monocarboxylic acidhuman xenobiotic metabolite
mandelic acid, (r)-isomer[no description available]low00mandelic acidhuman xenobiotic metabolite
phenylglyoxylic acid[no description available]low002-oxo monocarboxylic acidbiomarker;
human xenobiotic metabolite
2-phenyl-2-propanol[no description available]low00benzyl alcohols;
tertiary alcohol		human xenobiotic metabolite;
Mycoplasma genitalium metabolite
3-hydroxybenzeneacetic acid[no description available]low00monocarboxylic acid;
phenols		human xenobiotic metabolite
methoxyacetic acid[no description available]low00ether;
monocarboxylic acid		antineoplastic agent;
apoptosis inducer;
human xenobiotic metabolite;
mutagen
dihydroferulic acid[no description available]low00guaiacols;
monocarboxylic acid;
phenylpropanoid		antioxidant;
human xenobiotic metabolite;
mouse metabolite;
plant metabolite
1,6-diaminohexane[no description available]low00alkane-alpha,omega-diaminehuman xenobiotic metabolite
phenoxyacetic acid[no description available]low00aromatic ether;
monocarboxylic acid		allergen;
Aspergillus metabolite;
human xenobiotic metabolite;
plant growth retardant
3-phenoxybenzoic acid[no description available]low00phenoxybenzoic acidhuman xenobiotic metabolite;
marine xenobiotic metabolite
3,5,6-trichloro-2-pyridinol[no description available]low00chloropyridine;
hydroxypyridine;
pyridone		human urinary metabolite;
human xenobiotic metabolite;
marine xenobiotic metabolite
dimethyldiselenide[no description available]low00organoselenium compoundbacterial metabolite;
human xenobiotic metabolite;
mammalian metabolite;
plant metabolite
estetrol[no description available]low0015alpha-hydroxy steroid;
16alpha-hydroxy steroid;
17beta-hydroxy steroid;
3-hydroxy steroid;
steroid hormone		estrogen receptor agonist;
estrogen;
human metabolite;
human xenobiotic metabolite;
oral contraceptive
4-heptanone[no description available]low00dialkyl ketonebiomarker;
human urinary metabolite;
human xenobiotic metabolite;
rat metabolite
1-methyl-4-phenylpyridinium[no description available]low00pyridinium ionapoptosis inducer;
herbicide;
human xenobiotic metabolite;
neurotoxin
4-vinylphenol[no description available]low00phenolshuman urinary metabolite;
human xenobiotic metabolite
7-hydroxydehydroepiandrosterone[no description available]low0017-oxo steroid;
3beta-hydroxy-Delta(5)-steroid;
7alpha-hydroxy steroid;
androstanoid		anti-inflammatory agent;
antioxidant;
estrogen;
human xenobiotic metabolite;
rat metabolite
7-methylxanthine[no description available]low00oxopurine;
purine alkaloid		human xenobiotic metabolite;
mouse metabolite;
plant metabolite
1,3,5-trimethoxybenzene[no description available]low00methoxybenzenesbiomarker;
human xenobiotic metabolite
1-methyluric acid[no description available]low00oxopurinehuman xenobiotic metabolite;
mouse metabolite
6-methylthioguanine[no description available]low002-aminopurines;
thiopurine		human xenobiotic metabolite
phenylsulfate[no description available]low00aryl sulfatehuman xenobiotic metabolite
1,3,7,9-tetramethyluric acid[no description available]low00oxopurine;
purine alkaloid		analgesic;
anti-inflammatory agent;
human xenobiotic metabolite;
plant metabolite
mono-n-octyl phthalate[no description available]low00phthalic acid monoesterhuman xenobiotic metabolite
1,3,7-trimethylurate[no description available]low00oxopurinehuman blood serum metabolite;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite
n-hydroxy-4-aminobiphenyl[no description available]low00aminobiphenyl;
N-substituted amine		carcinogenic agent;
human xenobiotic metabolite
4-methylumbelliferyl sulfate[no description available]low00aryl sulfate;
coumarins		human xenobiotic metabolite
trimethylselenonium[no description available]low00organic cationhuman xenobiotic metabolite
1,7-dimethyluric acid[no description available]low00oxopurinehuman xenobiotic metabolite;
mouse metabolite
aspartyl-phenylalanine[no description available]low00dipeptidehuman blood serum metabolite;
human xenobiotic metabolite
1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid[no description available]low00alpha-amino acid;
aromatic amino acid;
beta-carboline alkaloid		human urinary metabolite;
human xenobiotic metabolite;
plant metabolite;
rat metabolite
aflatoxin q1[no description available]low00aflatoxin;
aromatic ether;
aromatic ketone		carcinogenic agent;
human xenobiotic metabolite
androsta-1,4,6-triene-3,17-dione[no description available]low0017-oxo steroid;
3-oxo-Delta(1),Delta(4)-steroid;
androstanoid		EC 1.14.14.14 (aromatase) inhibitor;
human xenobiotic metabolite
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine[no description available]low00hydroxylamine;
imidazopyridine		carcinogenic agent;
genotoxin;
human xenobiotic metabolite;
mouse metabolite;
mutagen;
neurotoxin;
rat metabolite
11-hydroxytestosterone[no description available]low0011beta-hydroxy steroid;
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
androstanoid;
C19-steroid		bacterial xenobiotic metabolite;
human xenobiotic metabolite;
marine metabolite
mono(2-ethyl-5-oxohexyl)phthalate[no description available]low00methyl ketone;
phthalic acid monoester		human urinary metabolite;
human xenobiotic metabolite
eseroline[no description available]low00phenols;
pyrroloindole		human xenobiotic metabolite;
opioid analgesic
2-(s-glutathionyl)hydroquinone[no description available]low00aryl sulfide;
glutathione conjugate;
hydroquinones		human xenobiotic metabolite;
nephrotoxic agent
tyramine o-sulfate[no description available]low00aryl sulfate;
primary amino compound;
zwitterion		human urinary metabolite;
human xenobiotic metabolite
5,6-didehydrosparteine[no description available]low00organic heterotetracyclic compound;
quinolizidine alkaloid;
tertiary amino compound		human xenobiotic metabolite
methanearsonous acid[no description available]low00arsonous acids;
one-carbon compound		carcinogenic agent;
human xenobiotic metabolite;
poison
methylselenic acid[no description available]low00one-carbon compound;
organoselenium compound		antineoplastic agent;
EC 3.5.1.98 (histone deacetylase) inhibitor;
human xenobiotic metabolite
glycyrrhetyl 3-monoglucuronide[no description available]low00beta-D-glucosiduronic acid;
enone;
monosaccharide derivative;
oxo dicarboxylic acid;
pentacyclic triterpenoid;
triterpenoid saponin		anti-allergic agent;
EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor;
human xenobiotic metabolite;
plant metabolite;
sweetening agent
13,14-dihydro-15-ketoprostaglandin e1[no description available]low00prostaglandins Ehuman xenobiotic metabolite
mono(2-ethyl-5-hydroxyhexyl) phthalate[no description available]low00phthalic acid monoesterhuman urinary metabolite;
human xenobiotic metabolite
n(4)-hydroxycytidine[no description available]low00ketoxime;
nucleoside analogue		anticoronaviral agent;
antiviral agent;
drug metabolite;
human xenobiotic metabolite
(-)-gallocatechin gallate[no description available]low00catechin;
gallate ester;
polyphenol		antineoplastic agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
human xenobiotic metabolite;
plant metabolite
hydroxydione[no description available]low0020-oxo steroid;
21-hydroxy steroid;
3-oxo-5beta-steroid;
primary alpha-hydroxy ketone		human xenobiotic metabolite
3,4-dihydroxyphenylpropionic acid[no description available]low00(dihydroxyphenyl)propanoic acidantioxidant;
human xenobiotic metabolite
indole-3-acetonitrile[no description available]low00indoles;
nitrile		auxin;
human xenobiotic metabolite;
plant hormone;
plant metabolite
3,4-didehydroretinoic acid[no description available]low00retinoid;
vitamin A		human xenobiotic metabolite
benzoylecgonine[no description available]low00benzoate ester;
tropane alkaloid		epitope;
human xenobiotic metabolite;
marine xenobiotic metabolite;
plant metabolite
sodium benzoate[no description available]low00organic sodium saltalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
cotinine[no description available]low00N-alkylpyrrolidine;
pyridines;
pyrrolidin-2-ones;
pyrrolidine alkaloid		antidepressant;
biomarker;
human xenobiotic metabolite;
plant metabolite
n-methylthiourea[no description available]low00thioureasdrug metabolite;
hepatotoxic agent;
human xenobiotic metabolite
4-nitrocatechol[no description available]low00C-nitro compound;
catechols		human xenobiotic metabolite;
lipoxygenase inhibitor
hydroxypioglitazone[no description available]low00aromatic ether;
pyridines;
thiazolidinediones		human xenobiotic metabolite
retinol palmitate[no description available]low00all-trans-retinyl ester;
retinyl palmitate		antioxidant;
Escherichia coli metabolite;
human xenobiotic metabolite
kaempferol[no description available]low007-hydroxyflavonol;
flavonols;
tetrahydroxyflavone		antibacterial agent;
geroprotector;
human blood serum metabolite;
human urinary metabolite;
human xenobiotic metabolite;
plant metabolite
leukotriene b5[no description available]low00dihydroxy monocarboxylic acid;
hydroxy polyunsaturated fatty acid;
leukotriene;
long-chain fatty acid		anti-inflammatory agent;
human xenobiotic metabolite;
rat metabolite
5,15-dihydroxy-6,8,11,13-eicosatetraenoic acid[no description available]low00dihydroxyicosatetraenoic acidhuman xenobiotic metabolite;
rat metabolite
arachidonic acid 5-hydroperoxide[no description available]low00HPETEhuman xenobiotic metabolite
muconic acid[no description available]low00muconic acidbiomarker;
human xenobiotic metabolite
ethyl arachidonate[no description available]low00long-chain fatty acid ethyl esterhuman blood serum metabolite;
human xenobiotic metabolite
trandolaprilat[no description available]low00dicarboxylic acid;
dipeptide;
organic heterobicyclic compound;
secondary amino compound;
tertiary carboxamide		antihypertensive agent;
drug metabolite;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
human xenobiotic metabolite
25-hydroxyvitamin d 2[no description available]low00hydroxycalciol;
seco-ergostane;
vitamin D		bone density conservation agent;
human xenobiotic metabolite;
nutraceutical
vitamin a2[no description available]low00retinoid;
vitamin A		human xenobiotic metabolite;
marine xenobiotic metabolite;
mouse metabolite
4-oxoretinoic acid[no description available]low00enone;
retinoid		human xenobiotic metabolite
15-hydroperoxy-5,8,11,13-eicosatetraenoic acid[no description available]low00HPETEhuman xenobiotic metabolite
5-oxo-15-hydroxy-6,8,11,13-eicosatetraenoic acid[no description available]low00enone;
hydroxy polyunsaturated fatty acid;
icosanoid;
long-chain fatty acid;
oxo fatty acid;
secondary allylic alcohol		human xenobiotic metabolite
5,12-dihydroxy-6,8,14-eicosatrienoic acid[no description available]low00dihydroxy monocarboxylic acid;
hydroxy polyunsaturated fatty acid;
leukotriene;
long-chain fatty acid		human urinary metabolite;
human xenobiotic metabolite
17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid[no description available]low00hydroxydocosahexaenoic acid;
secondary allylic alcohol		human xenobiotic metabolite
riddelliine n-oxide[no description available]low00diol;
macrocyclic lactone;
olefinic compound;
organic heterotricyclic compound;
primary alcohol;
pyrrolizine alkaloid;
tertiary alcohol;
tertiary amine oxide		carcinogenic agent;
genotoxin;
human xenobiotic metabolite;
Jacobaea metabolite;
mutagen;
rat metabolite
meso-zeaxanthin[no description available]low00carotenolanti-inflammatory agent;
antioxidant;
human xenobiotic metabolite;
marine metabolite
13(S)-HODE[no description available]low00HODEantineoplastic agent;
human xenobiotic metabolite;
mouse metabolite
3-hydroxyphenylacetate[no description available]low00hydroxy monocarboxylic acid anionhuman xenobiotic metabolite
1,25-dihydroxyergocalciferol[no description available]low00hydroxycalciol;
seco-ergostane;
vitamin D		bone density conservation agent;
human xenobiotic metabolite;
nutraceutical
demethylmirtazapine[no description available]low00benzazepine;
tetracyclic antidepressant		alpha-adrenergic antagonist;
anxiolytic drug;
H1-receptor antagonist;
histamine antagonist;
human xenobiotic metabolite;
serotonergic antagonist
5s,12r,18r-trihydroxy-6z,8e,10e,14z,16e-eicosapentaenoic acid[no description available]low00hydroxy polyunsaturated fatty acid;
long-chain fatty acid;
nonclassic icosanoid;
resolvin;
triol		anti-inflammatory agent;
human xenobiotic metabolite
resolvin d2[no description available]low00hydroxy polyunsaturated fatty acid;
resolvin;
secondary allylic alcohol;
triol		anti-inflammatory agent;
anti-obesity agent;
estrogen receptor agonist;
human xenobiotic metabolite;
rat metabolite
aflatoxin m1[no description available]low00aflatoxin;
aromatic ether;
aromatic ketone;
tertiary alcohol		Aspergillus metabolite;
human xenobiotic metabolite;
mammalian metabolite
protectin d1[no description available]low00dihydroxydocosahexaenoic acid;
protectin;
secondary allylic alcohol		anti-inflammatory agent;
apoptosis inhibitor;
hepatoprotective agent;
human xenobiotic metabolite;
neuroprotective agent;
PPARgamma agonist;
specialised pro-resolving mediator
resolvin e2[no description available]low00diol;
hydroxy polyunsaturated fatty acid;
resolvin;
secondary allylic alcohol		anti-inflammatory agent;
human xenobiotic metabolite;
rat metabolite
11,12-epoxy-5,8,14-eicosatrienoic acid[no description available]low0011,12-EEThuman xenobiotic metabolite
resolvin D4[no description available]low00hydroxy polyunsaturated fatty acid;
resolvin;
secondary allylic alcohol;
triol		anti-inflammatory agent;
human xenobiotic metabolite
resolvin d3[no description available]low00hydroxy polyunsaturated fatty acid;
resolvin;
secondary allylic alcohol;
triol		anti-inflammatory agent;
human xenobiotic metabolite
2-hydroxyatrazine[no description available]low00diamino-1,3,5-triazine;
monohydroxy-1,3,5-triazine		human xenobiotic metabolite;
marine xenobiotic metabolite
cannabidiolic acid[no description available]low00dihydroxybenzoic acid;
phytocannabinoid;
polyketide;
resorcinols
cannabigerolic acid[no description available]low00dihydroxybenzoic acid;
diterpenoid;
phytocannabinoid;
polyketide;
resorcinols
ConditionIndicatedRelationship StrengthStudiesTrials
Adipocere0low10
Algor Mortis0low10
ALS - Amyotrophic Lateral Sclerosis0medium11
Amyotrophic Lateral Sclerosis0medium11
Amyotrophic Lateral Sclerosis With Dementia0medium11
Amyotrophic Lateral Sclerosis-Parkinsonism-Dementia Complex 10medium11
Amyotrophic Lateral Sclerosis, Guam Form0medium11
Amyotrophic Lateral Sclerosis, Parkinsonism-Dementia Complex of Guam0medium11
Ataxia0low10
Ataxia, Appendicular0low10
Ataxia, Limb0low10
Ataxia, Motor0low10
Ataxia, Sensory0low10
Ataxia, Truncal0low10
Ataxy0low10
Aura0low10
Awakening Epilepsy0low10
Behavior Disorders0low10
Binge Alcohol Consumption0low10
Binge Drinking0low10
Bone Fractures0low10
Broken Bones0low10
Cannabis Abuse0medium113
Cannabis Dependence0medium113
Cannabis-Related Disorder0medium113
Charcot Disease0medium11
Chemical Dependence0low30
Chronic Disease0low10
Chronic Illness0low10
Chronically Ill0low10
Cognition Disorders0low10
Coordination Impairment0low10
Cruor0low10
Dementia With Amyotrophic Lateral Sclerosis0medium11
Diagnosis, Psychiatric0low10
Drug Abuse0low30
Drug Addiction0low30
Drug Dependence0low30
Drug Habituation0low30
Drug Use Disorders0low30
Drug Withdrawal Symptoms0medium31
Dyscoordination0low10
Dyssynergia0low10
Epilepsy0low10
Epilepsy, Cryptogenic0low10
Fractures, Bone0low10
Gehrig's Disease0medium11
Guam Disease0medium11
Guam Form of Amyotrophic Lateral Sclerosis0medium11
Hashish Abuse0medium113
Incoordination0low10
Intraocular Pressure0low10
Lack of Coordination0low10
Livor Mortis0low10
Lou Gehrig Disease0medium11
Lou Gehrig's Disease0medium11
Lou-Gehrigs Disease0medium11
Marihuana Abuse0medium113
Marijuana Abuse0medium113
Marijuana Dependence0medium113
Mental Disorders0low10
Mental Disorders, Severe0low10
Mental Illness0low10
Motor Neuron Disease, Amyotrophic Lateral Sclerosis0medium11
Neuroblastoma0low10
Organic Mental Disorders, Substance-Induced0low30
Overinclusion0low10
Postmortem Changes0low10
Pregnancy0low10
Prescription Drug Abuse0low30
Psychiatric Diagnosis0low10
Psychiatric Diseases0low10
Psychiatric Disorders0low10
Psychiatric Illness0low10
Psychoses0medium11
Psychosis0medium11
Psychosis, Brief Reactive0medium11
Psychotic Disorders0medium11
Schizoaffective Disorder0medium11
Schizophreniform Disorders0medium11
Seizure Disorder0low10
Sensitivity and Specificity0low80
Spiral Fractures0low10
Substance Abuse0low30
Substance Addiction0low30
Substance Dependence0low30
Substance Use0low30
Substance Use Disorders0low30
Substance Withdrawal Syndrome0medium31
Substance-Related Disorders0low30
Torsion Fractures0low10
Tremor, Rubral0low10
Withdrawal Symptoms0medium31

Research Highlights

Safety/Toxicity (1)

ArticleYear
Intraocular pressure, ocular toxicity and neurotoxicity in response to 11-hydroxy-delta 9-tetrahydrocannabinol and 1-nantradol.
Journal of ocular pharmacology,Summer, Volume: 1, Issue: 2		1985
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (1)

ArticleYear
Urinary excretion profiles of 11-nor-9-carboxy-delta9-tetrahydrocannabinol and 11-hydroxy-delta9-THC: cannabinoid metabolites to creatinine ratio study IV.
Forensic science international, Jul-16, Volume: 143, Issue: 2-3		2004
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (6)

ArticleYear
Minimal Physiologically Based Pharmacokinetic Model of Intravenously and Orally Administered Delta-9-Tetrahydrocannabinol in Healthy Volunteers.
European journal of drug metabolism and pharmacokinetics, Volume: 44, Issue: 5		2019
Single-dose pharmacokinetics and tolerability of oral delta-9- tetrahydrocannabinol in patients with amyotrophic lateral sclerosis.
Drug metabolism letters, Jun-01, Volume: 6, Issue: 2		2012
Identification of recent cannabis use: whole-blood and plasma free and glucuronidated cannabinoid pharmacokinetics following controlled smoked cannabis administration.
Clinical chemistry, Volume: 57, Issue: 10		2011
Plasma cannabinoid pharmacokinetics following controlled oral delta9-tetrahydrocannabinol and oromucosal cannabis extract administration.
Clinical chemistry, Volume: 57, Issue: 1		2011
Delta9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC plasma pharmacokinetics during and after continuous high-dose oral THC.
Clinical chemistry, Volume: 55, Issue: 12		2009
Molar volume relationships and the specific inhibition of a synaptosomal enzyme by psychoactive cannabinoids.
Journal of medicinal chemistry, Volume: 21, Issue: 12		1978
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (1)

ArticleYear
Plasma cannabinoid pharmacokinetics following controlled oral delta9-tetrahydrocannabinol and oromucosal cannabis extract administration.
Clinical chemistry, Volume: 57, Issue: 1		2011
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (8)

ArticleYear
Minimal Physiologically Based Pharmacokinetic Model of Intravenously and Orally Administered Delta-9-Tetrahydrocannabinol in Healthy Volunteers.
European journal of drug metabolism and pharmacokinetics, Volume: 44, Issue: 5		2019
Oral fluid and plasma cannabinoid ratios after around-the-clock controlled oral Δ(9)-tetrahydrocannabinol administration.
Clinical chemistry, Volume: 57, Issue: 11		2011
Antagonist-elicited cannabis withdrawal in humans.
Journal of clinical psychopharmacology, Volume: 31, Issue: 5		2011
Plasma cannabinoid pharmacokinetics following controlled oral delta9-tetrahydrocannabinol and oromucosal cannabis extract administration.
Clinical chemistry, Volume: 57, Issue: 1		2011
Delta9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC plasma pharmacokinetics during and after continuous high-dose oral THC.
Clinical chemistry, Volume: 55, Issue: 12		2009
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.
Therapeutic drug monitoring, Volume: 28, Issue: 4		2006
Effects of cannabinoids on progesterone release in cultures of rat luteal cells.
Life sciences, Nov-04, Volume: 37, Issue: 18		1985
Age-associated differences in cannabinoid-induced suppression of murine spleen, lymph node and thymus cell blastogenic responses.
Immunopharmacology, Volume: 14, Issue: 3		1987
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]