Page last updated: 2024-12-11

am-411

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID9799945
CHEMBL ID434351
MeSH IDM0480808

Synonyms (13)

Synonym
CHEMBL434351 ,
am-411
bdbm50169951
(6ar-trans)-3-adamantan-1-yl-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6h-benzo[c]chromen-1-ol
(6ar,10ar)-3-adamantan-1-yl-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6h-benzo[c]chromen-1-ol
(6ar,10ar)-3-(1-adamantyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
Q13424933
(-)-am 411
(6ar,10ar)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-tricyclo(3.3.1.13,7)dec-1-yl-6h-dibenzo(b,d)pyran-1-ol
212835-02-4
2K9WS7SUR3 ,
6h-dibenzo(b,d)pyran-1-ol, 6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-tricyclo(3.3.1.13,7)dec-1-yl-, (6ar,10ar)-
unii-2k9ws7sur3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cholesteryl ester transfer proteinHomo sapiens (human)Ki0.05200.00050.02200.0520AID311038
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki0.00680.00020.566510.0000AID238865; AID262340
Cannabinoid receptor 1Homo sapiens (human)Ki0.00680.00010.50779.6000AID311037; AID416355
Cannabinoid receptor 2 Homo sapiens (human)Ki0.05220.00000.415610.0000AID311038; AID416356; AID569313
Cannabinoid receptor 2Mus musculus (house mouse)Ki0.05200.00020.07970.7943AID496927
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 1Homo sapiens (human)EC50 (µMol)1.53000.00010.12752.2400AID740007
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (58)

Processvia Protein(s)Taxonomy
triglyceride metabolic processCholesteryl ester transfer proteinHomo sapiens (human)
lipid transportCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol metabolic processCholesteryl ester transfer proteinHomo sapiens (human)
negative regulation of macrophage derived foam cell differentiationCholesteryl ester transfer proteinHomo sapiens (human)
regulation of cholesterol effluxCholesteryl ester transfer proteinHomo sapiens (human)
phospholipid transportCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol transportCholesteryl ester transfer proteinHomo sapiens (human)
positive regulation of cholesterol transportCholesteryl ester transfer proteinHomo sapiens (human)
triglyceride transportCholesteryl ester transfer proteinHomo sapiens (human)
very-low-density lipoprotein particle remodelingCholesteryl ester transfer proteinHomo sapiens (human)
low-density lipoprotein particle remodelingCholesteryl ester transfer proteinHomo sapiens (human)
high-density lipoprotein particle remodelingCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol homeostasisCholesteryl ester transfer proteinHomo sapiens (human)
reverse cholesterol transportCholesteryl ester transfer proteinHomo sapiens (human)
phosphatidylcholine metabolic processCholesteryl ester transfer proteinHomo sapiens (human)
lipid homeostasisCholesteryl ester transfer proteinHomo sapiens (human)
phospholipid homeostasisCholesteryl ester transfer proteinHomo sapiens (human)
triglyceride homeostasisCholesteryl ester transfer proteinHomo sapiens (human)
positive regulation of phospholipid transportCholesteryl ester transfer proteinHomo 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)
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 (10)

Processvia Protein(s)Taxonomy
phospholipid transporter activityCholesteryl ester transfer proteinHomo sapiens (human)
lipid bindingCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol bindingCholesteryl ester transfer proteinHomo sapiens (human)
triglyceride bindingCholesteryl ester transfer proteinHomo sapiens (human)
phosphatidylcholine bindingCholesteryl ester transfer proteinHomo sapiens (human)
cholesterol transfer activityCholesteryl ester transfer proteinHomo 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)
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 (18)

Processvia Protein(s)Taxonomy
extracellular regionCholesteryl ester transfer proteinHomo sapiens (human)
extracellular spaceCholesteryl ester transfer proteinHomo sapiens (human)
vesicleCholesteryl ester transfer proteinHomo sapiens (human)
extracellular exosomeCholesteryl ester transfer proteinHomo sapiens (human)
high-density lipoprotein particleCholesteryl ester transfer proteinHomo 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)
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 (26)

Assay IDTitleYearJournalArticle
AID740005Hypothermic effect in Sprague-Dawley rat assessed as decrease in core body temperature at 10 mg/kg2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Novel adamantyl cannabinoids as CB1 receptor probes.
AID238865Inhibition of [3H]CP-55940 binding to cannabinoid receptor 1 of rat brain2005Journal of medicinal chemistry, Jul-14, Volume: 48, Issue:14
Adamantyl cannabinoids: a novel class of cannabinergic ligands.
AID262341Displacement of [3H]CP-55940 from mouse spleen CB2 receptor2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Structural modifications of the cannabinoid side chain towards C3-aryl and 1',1'-cycloalkyl-1'-cyano cannabinoids.
AID740014Selectivity ratio of Ki for mouse CB2 receptor to Ki for rat CB1 receptor2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Novel adamantyl cannabinoids as CB1 receptor probes.
AID740008Agonist activity at human CB1 receptor transfected in human U2OS cells assessed as beta-arrestin2-GFP aggregation after 40 mins relative to WIN55,212-22013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Novel adamantyl cannabinoids as CB1 receptor probes.
AID247066In vivo cannabinergic activity in rat after 90 min of dose administration (0.03-1.8 mg/kg) using drug discrimination assay2005Journal of medicinal chemistry, Jul-14, Volume: 48, Issue:14
Adamantyl cannabinoids: a novel class of cannabinergic ligands.
AID416356Binding affinity to CB2 receptor2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Quantitative structure-activity relationship (QSAR) for a series of novel cannabinoid derivatives using descriptors derived from semi-empirical quantum-chemical calculations.
AID740003Antinociceptive activity in Sprague-Dawley rat assessed as increase in tail-flick latency period at 0.05 mg/kg, sc by tail-flick test2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Novel adamantyl cannabinoids as CB1 receptor probes.
AID311038Binding affinity to CB2 receptor2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
The application of 3D-QSAR studies for novel cannabinoid ligands substituted at the C1' position of the alkyl side chain on the structural requirements for binding to cannabinoid receptors CB1 and CB2.
AID262340Displacement of [3H]CP-55940 from rat brain CB1 receptor2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Structural modifications of the cannabinoid side chain towards C3-aryl and 1',1'-cycloalkyl-1'-cyano cannabinoids.
AID740016Displacement of [3H]CP-55940 from mouse CB2 receptor expressed in mouse spleen membrane by competitive binding assay2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Novel adamantyl cannabinoids as CB1 receptor probes.
AID391587Displacement of [3H]CP-55940 from CB2 receptor in mouse spleen membrane2008Journal of medicinal chemistry, Oct-23, Volume: 51, Issue:20
Bornyl- and isobornyl-Delta8-tetrahydrocannabinols: a novel class of cannabinergic ligands.
AID416355Binding affinity to CB1 receptor2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Quantitative structure-activity relationship (QSAR) for a series of novel cannabinoid derivatives using descriptors derived from semi-empirical quantum-chemical calculations.
AID740002Antinociceptive activity in Sprague-Dawley rat assessed as increase in tail-flick latency period at 0.1 to 10 mg/kg, sc after 60 to 120 mins by tail-flick test2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Novel adamantyl cannabinoids as CB1 receptor probes.
AID391586Displacement of [3H]CP-55940 from CB1 receptor in rat brain synaptosome membrane2008Journal of medicinal chemistry, Oct-23, Volume: 51, Issue:20
Bornyl- and isobornyl-Delta8-tetrahydrocannabinols: a novel class of cannabinergic ligands.
AID247069In vivo cannabinergic activity in rat after 30 min of dose administration (0.03-1.8 mg/kg) using drug discrimination assay 2005Journal of medicinal chemistry, Jul-14, Volume: 48, Issue:14
Adamantyl cannabinoids: a novel class of cannabinergic ligands.
AID262342Selectivity for rat CB1 receptor over mouse CB2 receptor2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Structural modifications of the cannabinoid side chain towards C3-aryl and 1',1'-cycloalkyl-1'-cyano cannabinoids.
AID496926Displacement of [3H]CP-55940 from CB1 receptor in rat brain2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Heteroadamantyl cannabinoids.
AID311037Binding affinity to CB1 receptor2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
The application of 3D-QSAR studies for novel cannabinoid ligands substituted at the C1' position of the alkyl side chain on the structural requirements for binding to cannabinoid receptors CB1 and CB2.
AID740007Agonist activity at human CB1 receptor transfected in human U2OS cells assessed as beta-arrestin2-GFP aggregation after 40 mins2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Novel adamantyl cannabinoids as CB1 receptor probes.
AID569313Displacement of [3H]CP 55940 from human CB2 receptor in cell free system2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Three-dimensional quantitative structure-selectivity relationships analysis guided rational design of a highly selective ligand for the cannabinoid receptor 2.
AID496928Displacement of [3H]CP-55940 from human CB2 receptor expressed in HEK293 cell membranes2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Heteroadamantyl cannabinoids.
AID496927Displacement of [3H]CP-55940 from mouse CB2 receptor expressed in HEK293 cell membranes2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
Heteroadamantyl cannabinoids.
AID239117Inhibition of [3H]CP-55940 binding to cannabinoid receptor 2 of mouse spleen membranes2005Journal of medicinal chemistry, Jul-14, Volume: 48, Issue:14
Adamantyl cannabinoids: a novel class of cannabinergic ligands.
AID740017Displacement of [3H]CP-55940 from rat CB1 receptor expressed in rat brain membrane by competitive binding assay2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Novel adamantyl cannabinoids as CB1 receptor probes.
AID740001Antinociceptive activity in Sprague-Dawley rat assessed as increase in tail-flick latency period at 0.1 to 10 mg/kg, sc after 6 hrs by tail-flick test2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Novel adamantyl cannabinoids as CB1 receptor probes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (62.50)29.6817
2010's3 (37.50)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.42

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.42 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.42)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]