Page last updated: 2024-12-11

CB-13

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Description

naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: has antihyperalgesic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9799417
CHEMBL ID244403
CHEBI ID185985
SCHEMBL ID247361

Synonyms (29)

Synonym
naphthalen-1-yl-(4-pentoxynaphthalen-1-yl)methanone
CHEMBL244403 ,
bdbm50218116
naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone
432047-72-8
cb-13
CHEBI:185985
naphthalen-1-yl(4-(pentyloxy)naphthalen-1-yl)methanone;cb-13
A20544
1-naphthalenyl[4-(pentyloxy)-1-naphthalenyl]methanone
cb13 compound
1-naphthalenyl(4-(pentyloxy)-1-naphthalenyl)methanone
SCHEMBL247361
CCG-208739
cb 13
naphthalen-1-yl-(4-pentyloxy-naphthalen-1-yl)-methanone
DTXSID60430920
(naphthalen-1-yl)[4-(pentyloxy)naphthalen-1-yl]methanone
cra13
AKOS024457339
cra-13
unii-9xrj6055xt
9XRJ6055XT ,
methanone, 1-naphthalenyl(4-(pentyloxy)-1-naphthalenyl)-
mfcd11519954
Q5008954
HMS3742A19
1-naphthalenyl[4-(pentylox)-1-naphthalenyl]-methanone
cb13

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" In the present study, we evaluated the effects of acute and repeated dosing with the peripherally selective CB 1 -preferring agonist CB-13 on nociception and central CB 1 -related phenotypes in a model of inflammatory pain in mice."( The cannabinoid agonist CB-13 produces peripherally mediated analgesia in mice but elicits tolerance and signs of central nervous system activity with repeated dosing.
Brings, VE; Gereau, RW; Huynh, PN; Slivicki, RA; Yi, J, 2022
)
1.23
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzophenonesAny aromatic ketone in which the carbonyl group is bonded to 2 phenyl groups.
[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]

Protein Targets (9)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 2C8Homo sapiens (human)IC50 (µMol)0.01500.00081.88487.9000AID296812
Cytochrome P450 2D6Homo sapiens (human)IC50 (µMol)0.02200.00002.015110.0000AID296818
Cannabinoid receptor 1Rattus norvegicus (Norway rat)IC50 (µMol)0.02200.00020.660910.0000AID296818
Cannabinoid receptor 1Homo sapiens (human)IC50 (µMol)0.79750.00010.275310.0000AID1362836; AID296812
Cannabinoid receptor 1Homo sapiens (human)Ki0.03500.00010.50779.6000AID646621; AID662931
Cytochrome P450 2C19Homo sapiens (human)Ki0.01900.00010.830010.0000AID662932
Cannabinoid receptor 2 Homo sapiens (human)IC50 (µMol)2.69900.00081.58409.8000AID1362839; AID296813
Cannabinoid receptor 2 Homo sapiens (human)Ki0.01900.00000.415610.0000AID646624; AID662932
[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)
Cytochrome P450 1A2Homo sapiens (human)EC50 (µMol)0.00610.00030.20692.0000AID296814
Cytochrome P450 2E1Homo sapiens (human)EC50 (µMol)0.02790.00030.00960.0279AID296816
Cytochrome P450 3A4Homo sapiens (human)EC50 (µMol)0.00610.00010.23283.2000AID296814
Cannabinoid receptor 1Homo sapiens (human)EC50 (µMol)0.05040.00010.12752.2400AID296814; AID646622; AID662933
Cytochrome P450 2C19Homo sapiens (human)EC50 (µMol)0.00610.00030.00600.0123AID296814
Cannabinoid receptor 2 Homo sapiens (human)EC50 (µMol)0.02790.00030.15173.2800AID296816
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (85)

Processvia Protein(s)Taxonomy
steroid catabolic processCytochrome P450 1A2Homo sapiens (human)
porphyrin-containing compound metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 1A2Homo sapiens (human)
cholesterol metabolic processCytochrome P450 1A2Homo sapiens (human)
estrogen metabolic processCytochrome P450 1A2Homo sapiens (human)
toxin biosynthetic processCytochrome P450 1A2Homo sapiens (human)
post-embryonic developmentCytochrome P450 1A2Homo sapiens (human)
alkaloid metabolic processCytochrome P450 1A2Homo sapiens (human)
regulation of gene expressionCytochrome P450 1A2Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 1A2Homo sapiens (human)
dibenzo-p-dioxin metabolic processCytochrome P450 1A2Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
lung developmentCytochrome P450 1A2Homo sapiens (human)
methylationCytochrome P450 1A2Homo sapiens (human)
monocarboxylic acid metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 1A2Homo sapiens (human)
retinol metabolic processCytochrome P450 1A2Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 1A2Homo sapiens (human)
cellular respirationCytochrome P450 1A2Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 1A2Homo sapiens (human)
hydrogen peroxide biosynthetic processCytochrome P450 1A2Homo sapiens (human)
oxidative demethylationCytochrome P450 1A2Homo sapiens (human)
cellular response to cadmium ionCytochrome P450 1A2Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
long-chain fatty acid metabolic processCytochrome P450 2E1Homo sapiens (human)
lipid hydroxylationCytochrome P450 2E1Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2E1Homo sapiens (human)
steroid metabolic processCytochrome P450 2E1Homo sapiens (human)
response to bacteriumCytochrome P450 2E1Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2E1Homo sapiens (human)
carbon tetrachloride metabolic processCytochrome P450 2E1Homo sapiens (human)
benzene metabolic processCytochrome P450 2E1Homo sapiens (human)
4-nitrophenol metabolic processCytochrome P450 2E1Homo sapiens (human)
halogenated hydrocarbon metabolic processCytochrome P450 2E1Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2E1Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 2E1Homo sapiens (human)
lipid hydroxylationCytochrome P450 3A4Homo sapiens (human)
lipid metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid catabolic processCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid metabolic processCytochrome P450 3A4Homo sapiens (human)
cholesterol metabolic processCytochrome P450 3A4Homo sapiens (human)
androgen metabolic processCytochrome P450 3A4Homo sapiens (human)
estrogen metabolic processCytochrome P450 3A4Homo sapiens (human)
alkaloid catabolic processCytochrome P450 3A4Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 3A4Homo sapiens (human)
calcitriol biosynthetic process from calciolCytochrome P450 3A4Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D metabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D catabolic processCytochrome P450 3A4Homo sapiens (human)
retinol metabolic processCytochrome P450 3A4Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 3A4Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 3A4Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 3A4Homo sapiens (human)
oxidative demethylationCytochrome P450 3A4Homo sapiens (human)
lipid hydroxylationCytochrome P450 2C8Homo sapiens (human)
organic acid metabolic processCytochrome P450 2C8Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2C8Homo sapiens (human)
steroid metabolic processCytochrome P450 2C8Homo sapiens (human)
estrogen metabolic processCytochrome P450 2C8Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 2C8Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2C8Homo sapiens (human)
retinol metabolic processCytochrome P450 2C8Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 2C8Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2C8Homo sapiens (human)
icosanoid biosynthetic processCytochrome P450 2C8Homo sapiens (human)
oxidative demethylationCytochrome P450 2C8Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 2C8Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2D6Homo sapiens (human)
steroid metabolic processCytochrome P450 2D6Homo sapiens (human)
cholesterol metabolic processCytochrome P450 2D6Homo sapiens (human)
estrogen metabolic processCytochrome P450 2D6Homo sapiens (human)
coumarin metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid catabolic processCytochrome P450 2D6Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2D6Homo sapiens (human)
isoquinoline alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2D6Homo sapiens (human)
retinol metabolic processCytochrome P450 2D6Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2D6Homo sapiens (human)
negative regulation of bindingCytochrome P450 2D6Homo sapiens (human)
oxidative demethylationCytochrome P450 2D6Homo sapiens (human)
negative regulation of cellular organofluorine metabolic processCytochrome P450 2D6Homo sapiens (human)
arachidonic acid metabolic processCytochrome P450 2D6Homo sapiens (human)
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)
long-chain fatty acid metabolic processCytochrome P450 2C19Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2C19Homo sapiens (human)
steroid metabolic processCytochrome P450 2C19Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2C19Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 2C19Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2C19Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 2C19Homo 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 (39)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 1A2Homo sapiens (human)
iron ion bindingCytochrome P450 1A2Homo sapiens (human)
protein bindingCytochrome P450 1A2Homo sapiens (human)
electron transfer activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 1A2Homo sapiens (human)
enzyme bindingCytochrome P450 1A2Homo sapiens (human)
heme bindingCytochrome P450 1A2Homo sapiens (human)
demethylase activityCytochrome P450 1A2Homo sapiens (human)
caffeine oxidase activityCytochrome P450 1A2Homo sapiens (human)
aromatase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activityCytochrome P450 1A2Homo sapiens (human)
monooxygenase activityCytochrome P450 2E1Homo sapiens (human)
iron ion bindingCytochrome P450 2E1Homo sapiens (human)
oxidoreductase activityCytochrome P450 2E1Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, NAD(P)H as one donor, and incorporation of one atom of oxygenCytochrome P450 2E1Homo sapiens (human)
4-nitrophenol 2-monooxygenase activityCytochrome P450 2E1Homo sapiens (human)
oxygen bindingCytochrome P450 2E1Homo sapiens (human)
enzyme bindingCytochrome P450 2E1Homo sapiens (human)
heme bindingCytochrome P450 2E1Homo sapiens (human)
Hsp70 protein bindingCytochrome P450 2E1Homo sapiens (human)
Hsp90 protein bindingCytochrome P450 2E1Homo sapiens (human)
aromatase activityCytochrome P450 2E1Homo sapiens (human)
long-chain fatty acid omega-1 hydroxylase activityCytochrome P450 2E1Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2E1Homo sapiens (human)
arachidonic acid epoxygenase activityCytochrome P450 2E1Homo sapiens (human)
monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
steroid bindingCytochrome P450 3A4Homo sapiens (human)
iron ion bindingCytochrome P450 3A4Homo sapiens (human)
protein bindingCytochrome P450 3A4Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
oxidoreductase activityCytochrome P450 3A4Homo sapiens (human)
oxygen bindingCytochrome P450 3A4Homo sapiens (human)
enzyme bindingCytochrome P450 3A4Homo sapiens (human)
heme bindingCytochrome P450 3A4Homo sapiens (human)
vitamin D3 25-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
caffeine oxidase activityCytochrome P450 3A4Homo sapiens (human)
quinine 3-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
testosterone 6-beta-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
aromatase activityCytochrome P450 3A4Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
monooxygenase activityCytochrome P450 2C8Homo sapiens (human)
iron ion bindingCytochrome P450 2C8Homo sapiens (human)
protein bindingCytochrome P450 2C8Homo sapiens (human)
arachidonic acid epoxygenase activityCytochrome P450 2C8Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 2C8Homo sapiens (human)
caffeine oxidase activityCytochrome P450 2C8Homo sapiens (human)
aromatase activityCytochrome P450 2C8Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 2C8Homo sapiens (human)
heme bindingCytochrome P450 2C8Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2C8Homo sapiens (human)
monooxygenase activityCytochrome P450 2D6Homo sapiens (human)
iron ion bindingCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activityCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2D6Homo sapiens (human)
heme bindingCytochrome P450 2D6Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
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)
monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
iron ion bindingCytochrome P450 2C19Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 2C19Homo sapiens (human)
oxidoreductase activityCytochrome P450 2C19Homo sapiens (human)
(S)-limonene 6-monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
(S)-limonene 7-monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
oxygen bindingCytochrome P450 2C19Homo sapiens (human)
enzyme bindingCytochrome P450 2C19Homo sapiens (human)
heme bindingCytochrome P450 2C19Homo sapiens (human)
(R)-limonene 6-monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
aromatase activityCytochrome P450 2C19Homo sapiens (human)
long-chain fatty acid omega-1 hydroxylase activityCytochrome P450 2C19Homo sapiens (human)
arachidonic acid epoxygenase activityCytochrome P450 2C19Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2C19Homo 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 (17)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
mitochondrial inner membraneCytochrome P450 2E1Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2E1Homo sapiens (human)
cytoplasmCytochrome P450 2E1Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2E1Homo sapiens (human)
cytoplasmCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 3A4Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2C8Homo sapiens (human)
plasma membraneCytochrome P450 2C8Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C8Homo sapiens (human)
cytoplasmCytochrome P450 2C8Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C8Homo sapiens (human)
mitochondrionCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulumCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2D6Homo sapiens (human)
cytoplasmCytochrome P450 2D6Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2D6Homo sapiens (human)
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)
endoplasmic reticulum membraneCytochrome P450 2C19Homo sapiens (human)
plasma membraneCytochrome P450 2C19Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C19Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C19Homo sapiens (human)
cytoplasmCytochrome P450 2C19Homo 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 (54)

Assay IDTitleYearJournalArticle
AID296822Volume of distribution at steady state in Wistar rat at 1 mg/kg, iv2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID662958Ratio of drug level in brain to plasma in rat by microdialysis assay2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamides as a novel class of cannabinoid receptors agonists with low CNS penetration.
AID296823Total clearance in Wistar rat at 1 mg/kg, iv2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID646623Agonist activity at human CB1 receptor expressed in HEK293 EBNA cells by [35S]GTPgamma binding assay relative to Win55,212-22012Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4
γ-Carbolines: a novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration.
AID1362836Displacement of [3H]SR141716A from membrane bound human CB1 receptor after 1 hr by beta scintillation counting method
AID296815Agonist activity at human CB1 receptor expressed in HEK293 cells assessed as reversal of forskolin-evoked cAMP accumulation relative to CP-559402007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296821Half life in Wistar rat at 1 mg/kg, iv2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296824AUC (0 to infinity) in Wistar rat at 1 mg/kg, iv2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID646624Binding affinity to human CB2 receptor2012Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4
γ-Carbolines: a novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration.
AID662934Agonist activity at human CB1 receptor expressed in HEK293 cells assessed as [35S]GTPgamma binding relative to WIN55212-22012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamides as a novel class of cannabinoid receptors agonists with low CNS penetration.
AID296832Inhibition of CYP2C8 in human liver microsomes2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296827AUC (0 to infinity) in Wistar rat at 3.4 mg/kg, po2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296819Antihyperalgesic activity in rat assessed as reversal of hyperalgesia at 3 mg/kg, po after 1 hr2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296835Inhibition of CYP2D6 in human liver microsomes2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID1362837Displacement of [3H]CP55940 from membrane bound human CB2 receptor at 100 uM after 1 hr by beta scintillation counting method relative to control
AID1362834Displacement of [3H]SR141716A from membrane bound human CB1 receptor at 100 uM after 1 hr by beta scintillation counting method relative to control
AID296829Intrinsic clearance in rat liver microsomes2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296820Antihyperalgesic activity in rat assessed as reversal of hyperalgesia2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296838Plasma protein binding2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296840Cmax in Wistar rat at 3 mg/kg, po after 1 hr2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296831Inhibition of CYP1A2 in human liver microsomes2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296818Inhibition of rat CB1 receptor2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID646683Ratio of drug uptake in brain to plasma of Sprague-Dawley rat at 1 mg/kg, sc2012Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4
γ-Carbolines: a novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration.
AID646622Agonist activity at human CB1 receptor expressed in HEK293 EBNA cells by [35S]GTPgamma binding assay2012Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4
γ-Carbolines: a novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration.
AID296828Bioavailability in Wistar rat at 3.4 mg/kg, po2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296813Displacement of [3H]CP-55940 human CB2 receptor expressed in CHOK1 cells2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296816Agonist activity at human CB2 receptor expressed in CHOK1 cells assessed as reversal of forskolin-evoked cAMP accumulation2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296812Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296825Tmax in Wistar rat at 3.4 mg/kg, po2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID1362839Displacement of [3H]CP55940 from membrane bound human CB2 receptor after 1 hr by beta scintillation counting method
AID646621Displacement of [3H]-CP55,940 from human CB1 receptor expressed in HEK293 cells2012Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4
γ-Carbolines: a novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration.
AID296834Inhibition of CYP2C19 in human liver microsomes2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296814Agonist activity at human CB1 receptor expressed in HEK293 cells assessed as reversal of forskolin-evoked cAMP accumulation2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID662937Thermodynamic solubility of the compound at pH 7.42012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamides as a novel class of cannabinoid receptors agonists with low CNS penetration.
AID662938Apparent permeability from apical to basal side of human Caco2 cells at 10 uM2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamides as a novel class of cannabinoid receptors agonists with low CNS penetration.
AID296841Drug level in brain in Wistar rat after 4 hrs2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296817Agonist activity at human CB2 receptor expressed in CHOK1 cells assessed as reversal of forskolin-evoked cAMP accumulation relative to CP-559402007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID662936Inhibition of human ERG2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamides as a novel class of cannabinoid receptors agonists with low CNS penetration.
AID296836Inhibition of CYP2E1 in human liver microsomes2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID1362842Selectivity ratio of compound effect for displacement of [3H]CP55940 from membrane bound human CB2 receptor at 10 uM to compound effect for displacement of [3H]SR141716A from membrane bound human CB1 receptor at 10 uM
AID662931Displacement of [3H]CP55940 from human CB1 receptor expressed in HEK293 cells2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamides as a novel class of cannabinoid receptors agonists with low CNS penetration.
AID1362840Selectivity ratio of IC50 for displacement of [3H]SR141716A from membrane bound human CB1 receptor to IC50 for displacement of [3H]CP55940 from membrane bound human CB2 receptor
AID296830Intrinsic clearance in human liver microsomes2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296839Partition coefficient, log P of the compound2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID662932Binding affinity to human CB2 receptor2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamides as a novel class of cannabinoid receptors agonists with low CNS penetration.
AID296833Inhibition of CYP2C9 in human liver microsomes2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID296837Inhibition of CYP3A4 in human liver microsomes2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID1362835Displacement of [3H]SR141716A from membrane bound human CB1 receptor at 10 uM after 1 hr by beta scintillation counting method relative to control
AID662935Intrinsic clearance in human liver microsomes at 1 uM in presence of NADPH2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamides as a novel class of cannabinoid receptors agonists with low CNS penetration.
AID296826Cmax in Wistar rat at 3.4 mg/kg, po2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
AID662933Agonist activity at human CB1 receptor expressed in HEK293 cells assessed as [35S]GTPgamma binding2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamides as a novel class of cannabinoid receptors agonists with low CNS penetration.
AID1362838Displacement of [3H]CP55940 from membrane bound human CB2 receptor at 10 uM after 1 hr by beta scintillation counting method relative to control
AID646627Aqueous solubility of the compound at pH 7.42012Bioorganic & medicinal chemistry letters, Feb-15, Volume: 22, Issue:4
γ-Carbolines: a novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration.
AID493017Wombat Data for BeliefDocking2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (7.14)29.6817
2010's10 (71.43)24.3611
2020's3 (21.43)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 51.25

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index51.25 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.23 (4.65)
Search Engine Demand Index76.73 (26.88)
Search Engine Supply Index2.02 (0.95)

This Compound (51.25)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]