Page last updated: 2024-12-11

jwh-133

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Description

1,1-dimethylbutyl-1-deoxy-Delta(9)-THC: a CB2 receptor agonists; no further information available on 8/2001 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

JWH-133 : A dibenzopyran that is Delta(9)-tetrahydrocannabinol which is lacking the hydroxy group and in which the pentyl group at position 3 has been replaced by a 1,1-dimethylbutyl group. A potent and highly selective CB2 receptor agonist. [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 CID6918505
CHEMBL ID371214
CHEBI ID146243
SCHEMBL ID1517632
MeSH IDM0395648

Synonyms (39)

Synonym
gtpl747
jwh-133
1,1-dimethylbutyl-1-deoxy-delta(9)-thc
jwh133
CHEMBL371214 ,
bdbm50180036
(6ar,10ar)-3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6hdibenzo[b,d]pyran
(6ar,10ar)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene
(6ar,10ar)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydro-6h-benzo[c]chromene
259869-55-1
CHEBI:146243
jw 133
(6ar,10ar)-3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6h-dibenzo[b,d]pyran
jwh 133
BCP9000807
jw-133/jw133
BCP0726000079
tdg8048rda ,
unii-tdg8048rda
J-501647
HY-15854
CS-5513
AKOS024456536
SCHEMBL1517632
(6ar,10ar)-3-(1,1-dimethyl-butyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6h-benzo[c]chromene
jwh 133 (in tocrisolvetrade mark 100)
YSBFLLZNALVODA-RBUKOAKNSA-N ,
DTXSID30426077
EX-A1014
(6ar,10ar)-6,6,9-trimethyl-3-(2-methyl-2-pentanyl)-6a,7,10,10a-tetrahydro-6h-benzo[c]chromene
6h-dibenzo(b,d)pyran, 3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-, (6ar,10ar)-
(6ar,10ar)-3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6h-dibenzo(b,d)pyran
BCP22587
Q6109195
6h-dibenzo[b,d]pyran, 3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-, (6ar,10ar)-
3-(1,1-dimethylbutyl)-6ar,7,10,10ar-tetrahydro-6,6,9-trimethyl-6h-dibenzo[b,d]pyran
nsc792741
nsc-792741
BJ164539
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (7)

RoleDescription
CB2 receptor agonistA cannabinoid receptor agonist that binds to and activates type 2 cannabinoid receptors.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
vasodilator agentA drug used to cause dilation of the blood vessels.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
apoptosis inhibitorAny substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
analgesicAn agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
opioid analgesicA narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
[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 (3)

ClassDescription
dibenzopyranAny organic heteropolycyclic compound based on a skeleton consisting of a pyran ring fused with two benzene rings.
organic heterotricyclic compoundAn organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
benzochromene
[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)
Androgen receptorRattus norvegicus (Norway rat)Ki0.00340.00031.21858.9270AID482751
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki0.45230.00020.566510.0000AID1127485; AID1204170; AID537503
Cannabinoid receptor 1Homo sapiens (human)Ki0.55570.00010.50779.6000AID1067338; AID1167198; AID1191307; AID1204169; AID1638016; AID1800327; AID375659; AID412565; AID412568; AID482750; AID569312; AID617963; AID660461
Prostaglandin G/H synthase 1Homo sapiens (human)Ki0.00300.00301.37704.0000AID1067337
Cannabinoid receptor 2 Homo sapiens (human)IC50 (µMol)0.08180.00081.58409.8000AID1626206
Cannabinoid receptor 2 Homo sapiens (human)Ki0.00480.00000.415610.0000AID1067337; AID1127483; AID1167199; AID1191308; AID1204170; AID1626199; AID1638015; AID1800327; AID259197; AID375660; AID412566; AID412569; AID482751; AID537504; AID569313; AID617964; AID660462
[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)
Glutamate receptor 1Rattus norvegicus (Norway rat)EC50 (µMol)1.07040.00411.89638.7000AID257800; AID259201
Glutamate receptor 2Rattus norvegicus (Norway rat)EC50 (µMol)1.07040.00411.62517.6000AID257800; AID259201
Glutamate receptor 3Rattus norvegicus (Norway rat)EC50 (µMol)1.07040.00411.17063.5000AID257800; AID259201
Glutamate receptor 4Rattus norvegicus (Norway rat)EC50 (µMol)1.07040.00411.13393.5000AID257800; AID259201
Cannabinoid receptor 1Rattus norvegicus (Norway rat)EC50 (µMol)1.99530.00020.19211.9953AID257800
Cannabinoid receptor 2 Homo sapiens (human)EC50 (µMol)0.18020.00030.15173.2800AID1658165; AID259201; AID537506
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (45)

Processvia Protein(s)Taxonomy
positive regulation of acute inflammatory response to antigenic stimulusCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
spermatogenesisCannabinoid receptor 1Homo sapiens (human)
axonal fasciculationCannabinoid receptor 1Homo sapiens (human)
response to nutrientCannabinoid receptor 1Homo sapiens (human)
memoryCannabinoid receptor 1Homo sapiens (human)
positive regulation of neuron projection developmentCannabinoid receptor 1Homo sapiens (human)
negative regulation of serotonin secretionCannabinoid receptor 1Homo sapiens (human)
positive regulation of fever generationCannabinoid receptor 1Homo sapiens (human)
negative regulation of fatty acid beta-oxidationCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, GABAergicCannabinoid receptor 1Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 1Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 1Homo sapiens (human)
negative regulation of dopamine secretionCannabinoid receptor 1Homo sapiens (human)
response to nicotineCannabinoid receptor 1Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 1Homo sapiens (human)
response to cocaineCannabinoid receptor 1Homo sapiens (human)
glucose homeostasisCannabinoid receptor 1Homo sapiens (human)
positive regulation of apoptotic processCannabinoid receptor 1Homo sapiens (human)
response to ethanolCannabinoid receptor 1Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 1Homo sapiens (human)
negative regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
positive regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
regulation of insulin secretionCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicCannabinoid receptor 1Homo sapiens (human)
maternal process involved in female pregnancyCannabinoid receptor 1Homo sapiens (human)
regulation of feeding behaviorCannabinoid receptor 1Homo sapiens (human)
regulation of penile erectionCannabinoid receptor 1Homo sapiens (human)
retrograde trans-synaptic signaling by endocannabinoidCannabinoid receptor 1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationCannabinoid receptor 1Homo sapiens (human)
trans-synaptic signaling by endocannabinoid, modulating synaptic transmissionCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 1Homo sapiens (human)
prostaglandin biosynthetic processProstaglandin G/H synthase 1Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 1Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 1Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 1Homo sapiens (human)
regulation of cell population proliferationProstaglandin G/H synthase 1Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 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 (9)

Processvia Protein(s)Taxonomy
cannabinoid receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 1Homo sapiens (human)
identical protein bindingCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor activityCannabinoid receptor 1Homo sapiens (human)
peroxidase activityProstaglandin G/H synthase 1Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 1Homo sapiens (human)
protein bindingProstaglandin G/H synthase 1Homo sapiens (human)
heme bindingProstaglandin G/H synthase 1Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 1Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 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 (19)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 1Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
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)
photoreceptor outer segmentProstaglandin G/H synthase 1Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 1Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 1Homo sapiens (human)
Golgi apparatusProstaglandin G/H synthase 1Homo sapiens (human)
intracellular membrane-bounded organelleProstaglandin G/H synthase 1Homo sapiens (human)
extracellular exosomeProstaglandin G/H synthase 1Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 1Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 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 (67)

Assay IDTitleYearJournalArticle
AID375659Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HEK293 cells2009Journal of medicinal chemistry, Jun-25, Volume: 52, Issue:12
Rational design, synthesis, and pharmacological properties of new 1,8-naphthyridin-2(1H)-on-3-carboxamide derivatives as highly selective cannabinoid-2 receptor agonists.
AID537505Selectivity ratio of IC50 for CB1 receptor in Sprague-Dawley rat brain membranes to IC50 for human CB2 receptor2010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor.
AID1127485Binding affinity to rat CB1 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID537506Agonist activity at human CB2 receptor expressed in CHO cells assessed as stimulation of [35S]GTPgammaS binding after 1.5 hrs by liquid scintillation spectrophotometry2010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor.
AID1191308Displacement of [3H]CP55,940 from human recombinant CB2 receptor expressed in HEK293 cell membranes after 90 mins2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, biological activity and molecular modeling of new biphenylic carboxamides as potent and selective CB2 receptor ligands.
AID1626207Agonist activity at human CB2 receptor expressed in HEK293 cell membranes assessed as induction of [35S]-GTPgammaS binding after 60 mins by liquid scintillation spectrometric method2016Journal of medicinal chemistry, 07-28, Volume: 59, Issue:14
Chromenopyrazole, a Versatile Cannabinoid Scaffold with in Vivo Activity in a Model of Multiple Sclerosis.
AID1167198Displacement of [3H]CP-55,940 from human recombinant CB1R expressed in HEK-293 cells after 90 mins by liquid scintillation counting2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
CB2-selective cannabinoid receptor ligands: synthesis, pharmacological evaluation, and molecular modeling investigation of 1,8-Naphthyridin-2(1H)-one-3-carboxamides.
AID272970Selectivity for DBA/J2 mouse CB2 receptor over CB1 receptor2006Journal of medicinal chemistry, Oct-05, Volume: 49, Issue:20
Design, synthesis, and biological evaluation of new 1,8-naphthyridin-4(1H)-on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives as CB2 selective agonists.
AID1706279Agonist activity at CB2R in LPS induced mouse BV2 cells assessed as decrease in IL6 secretion at 10 uM preincubated for 30 mins followed by LPS stimulation for 4 hrs by ELISA2020European journal of medicinal chemistry, Dec-15, Volume: 208The endocannabinoid system dual-target ligand N-cycloheptyl-1,2-dihydro-5-bromo-1-(4-fluorobenzyl)-6-methyl-2-oxo-pyridine-3-carboxamide improves disease severity in a mouse model of multiple sclerosis.
AID412568Binding affinity to CB1 receptor2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Discovery of novel CB2 receptor ligands by a pharmacophore-based virtual screening workflow.
AID272969Displacement of [3H]CP-55940 from CB2 receptor in DBA/J2 mouse spleen2006Journal of medicinal chemistry, Oct-05, Volume: 49, Issue:20
Design, synthesis, and biological evaluation of new 1,8-naphthyridin-4(1H)-on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives as CB2 selective agonists.
AID682881Agonist activity at human CB2 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP level at 10 uM by scintillation counting2012Journal of medicinal chemistry, Jun-14, Volume: 55, Issue:11
Design, synthesis, and pharmacological characterization of indol-3-ylacetamides, indol-3-yloxoacetamides, and indol-3-ylcarboxamides: potent and selective CB2 cannabinoid receptor inverse agonists.
AID412569Binding affinity to CB2 receptor2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Discovery of novel CB2 receptor ligands by a pharmacophore-based virtual screening workflow.
AID259201Effect on [35S]GTP-gamma-S binding to human CB2 receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Novel 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives as new CB2 cannabinoid receptors agonists: synthesis, pharmacological properties and molecular modeling.
AID537507Agonist activity at human CB2 receptor expressed in CHO cells assessed as stimulation of [35S]GTPgammaS binding after 1.5 hrs by liquid scintillation spectrophotometry relative to CP-559402010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor.
AID1127483Binding affinity to human CB2 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID1204178Cytotoxicity against human LNCAP cells expressing CB2 receptor assessed as decrease in cell viability after 72 hrs by neutral red uptake and accumulation assay2015European journal of medicinal chemistry, Jun-05, Volume: 97New quinolone- and 1,8-naphthyridine-3-carboxamides as selective CB2 receptor agonists with anticancer and immuno-modulatory activity.
AID1626201Selectivity ratio of Ki for rat brain CB1 receptor to Ki for human CB2 receptor2016Journal of medicinal chemistry, 07-28, Volume: 59, Issue:14
Chromenopyrazole, a Versatile Cannabinoid Scaffold with in Vivo Activity in a Model of Multiple Sclerosis.
AID660462Displacement of [3H]CP55940 from recombinant human CB2 receptor expressed in human HEK293 cell membrane after 90 mins2012European journal of medicinal chemistry, Jun, Volume: 52Rational design, synthesis and anti-proliferative properties of new CB2 selective cannabinoid receptor ligands: an investigation of the 1,8-naphthyridin-2(1H)-one scaffold.
AID1706250Agonist activity at CB2R in LPS induced mouse BV2 cells assessed as increase in IL-10 secretion at 10 uM preincubated for 30 mins followed by LPS stimulation for 4 hrs by ELISA2020European journal of medicinal chemistry, Dec-15, Volume: 208The endocannabinoid system dual-target ligand N-cycloheptyl-1,2-dihydro-5-bromo-1-(4-fluorobenzyl)-6-methyl-2-oxo-pyridine-3-carboxamide improves disease severity in a mouse model of multiple sclerosis.
AID1638016Displacement of [3H]-CP-55940 from human CB1 receptor expressed in CHO cell membranes after 1 hr by beta-counting analysis2019European journal of medicinal chemistry, Mar-01, Volume: 165Benzo[d]thiazol-2(3H)-ones as new potent selective CB
AID1067337Displacement of [3H]CP55,940 from human recombinant CB2 receptor expressed in HEK293 cell membranes after 90 mins2014European journal of medicinal chemistry, Mar-03, Volume: 741,2-Dihydro-2-oxopyridine-3-carboxamides: the C-5 substituent is responsible for functionality switch at CB2 cannabinoid receptor.
AID1191309Selectivity index, ratio of Ki for human recombinant CB1 receptor expressed in HEK293 cell membranes to Ki for human recombinant CB2 receptor expressed in HEK293 cell membranes2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, biological activity and molecular modeling of new biphenylic carboxamides as potent and selective CB2 receptor ligands.
AID1204170Displacement of [3H]-CP-55940 from recombinant human CB2 receptor overexpressed in HEK293 cell membranes after 90 mins2015European journal of medicinal chemistry, Jun-05, Volume: 97New quinolone- and 1,8-naphthyridine-3-carboxamides as selective CB2 receptor agonists with anticancer and immuno-modulatory activity.
AID1853228Antiproliferative activity against human KNS-42 cells assessed as cell growth inhibition incubated for 72 hrs by MTT assay
AID1658165Agonist activity at recombinant human CB2R expressed in CHOK1 cells assessed as inhibition of NKH477-stimulated intracellular cAMP levels after 30 mins by chemiluminescent detection based cAMP Hunter assay
AID1638015Displacement of [3H]-CP-55940 from human CB2 receptor expressed in CHO cell membranes after 1 hr by beta-counting analysis2019European journal of medicinal chemistry, Mar-01, Volume: 165Benzo[d]thiazol-2(3H)-ones as new potent selective CB
AID617963Binding affinity to CB1 receptor2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Fluorinated cannabinoid CB2 receptor ligands: synthesis and in vitro binding characteristics of 2-oxoquinoline derivatives.
AID302382Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO cells2007Journal of medicinal chemistry, Nov-01, Volume: 50, Issue:22
Pharmacomodulations around the 4-oxo-1,4-dihydroquinoline-3-carboxamides, a class of potent CB2-selective cannabinoid receptor ligands: consequences in receptor affinity and functionality.
AID1204169Displacement of [3H]-CP-55940 from recombinant human CB1 receptor overexpressed in HEK293 cell membranes after 90 mins2015European journal of medicinal chemistry, Jun-05, Volume: 97New quinolone- and 1,8-naphthyridine-3-carboxamides as selective CB2 receptor agonists with anticancer and immuno-modulatory activity.
AID660461Displacement of [3H]CP55940 from recombinant human CB1 receptor expressed in human HEK293 cell membrane after 90 mins2012European journal of medicinal chemistry, Jun, Volume: 52Rational design, synthesis and anti-proliferative properties of new CB2 selective cannabinoid receptor ligands: an investigation of the 1,8-naphthyridin-2(1H)-one scaffold.
AID257800Displacement of [35S]GTP-gamma-S from rat cerebellar CB1 receptor2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
3D-QSAR studies on cannabinoid CB1 receptor agonists: G-protein activation as biological data.
AID617964Binding affinity to CB2 receptor2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Fluorinated cannabinoid CB2 receptor ligands: synthesis and in vitro binding characteristics of 2-oxoquinoline derivatives.
AID1626206Agonist activity at human CB2 receptor expressed in HEK293 cell membranes assessed as inhibition of forskolin-stimulated cAMP accumulation after 60 mins by HTRF assay2016Journal of medicinal chemistry, 07-28, Volume: 59, Issue:14
Chromenopyrazole, a Versatile Cannabinoid Scaffold with in Vivo Activity in a Model of Multiple Sclerosis.
AID302384Activity at human CB2 receptor expressed in CHO cells assessed as stimulated [35S]GTP-gamma-S binding relative to control2007Journal of medicinal chemistry, Nov-01, Volume: 50, Issue:22
Pharmacomodulations around the 4-oxo-1,4-dihydroquinoline-3-carboxamides, a class of potent CB2-selective cannabinoid receptor ligands: consequences in receptor affinity and functionality.
AID412566Displacement of [3H]CP-55940 from human recombinant CB2 receptor2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Discovery of novel CB2 receptor ligands by a pharmacophore-based virtual screening workflow.
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.
AID569312Displacement of [3H]CP 55940 from human CB1 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.
AID1601909Antiproliferative activity against normal human derived lymphoblast cells at 5 uM after 72 hrs by MTT assay2019European journal of medicinal chemistry, Mar-15, Volume: 166Indazolylketones as new multitarget cannabinoid drugs.
AID1191307Displacement of [3H]CP55,940 from human recombinant CB1 receptor expressed in HEK293 cell membranes after 90 mins2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, biological activity and molecular modeling of new biphenylic carboxamides as potent and selective CB2 receptor ligands.
AID375660Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HEK293 cells2009Journal of medicinal chemistry, Jun-25, Volume: 52, Issue:12
Rational design, synthesis, and pharmacological properties of new 1,8-naphthyridin-2(1H)-on-3-carboxamide derivatives as highly selective cannabinoid-2 receptor agonists.
AID272968Displacement of [3H]CP-55940 from CB1 receptor in DBA/J2 mouse brain2006Journal of medicinal chemistry, Oct-05, Volume: 49, Issue:20
Design, synthesis, and biological evaluation of new 1,8-naphthyridin-4(1H)-on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives as CB2 selective agonists.
AID537504Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO cells after 1 hr by liquid scintillation spectrophotometry2010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor.
AID569314Selectivity ratio of Ki for human CB1 to Ki for human CB22011European 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.
AID302381Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells2007Journal of medicinal chemistry, Nov-01, Volume: 50, Issue:22
Pharmacomodulations around the 4-oxo-1,4-dihydroquinoline-3-carboxamides, a class of potent CB2-selective cannabinoid receptor ligands: consequences in receptor affinity and functionality.
AID412570Selectivity ratio of Ki for CB1 receptor to Ki for CB2 receptor2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Discovery of novel CB2 receptor ligands by a pharmacophore-based virtual screening workflow.
AID412567Selectivity ratio of Ki for human CB1 receptor to Ki for human CB2 receptor2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Discovery of novel CB2 receptor ligands by a pharmacophore-based virtual screening workflow.
AID682876Agonist activity at human CB2 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP level at 1 uM by scintillation counting2012Journal of medicinal chemistry, Jun-14, Volume: 55, Issue:11
Design, synthesis, and pharmacological characterization of indol-3-ylacetamides, indol-3-yloxoacetamides, and indol-3-ylcarboxamides: potent and selective CB2 cannabinoid receptor inverse agonists.
AID259200Effect on human CB2 receptor stimulation by [35S]GTP-gamma-S binding at 10 uM (basal value set at 100%)2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Novel 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives as new CB2 cannabinoid receptors agonists: synthesis, pharmacological properties and molecular modeling.
AID482750Binding affinity to cannabinoid CB1 receptor2010Journal of medicinal chemistry, Jun-10, Volume: 53, Issue:11
Emerging targets in osteoporosis disease modification.
AID1638017Selectivity index, ratio of Ki for human CB1 receptor expressed in CHO cell membranes to Ki for human CB2 receptor expressed in CHO cell membranes2019European journal of medicinal chemistry, Mar-01, Volume: 165Benzo[d]thiazol-2(3H)-ones as new potent selective CB
AID482751Binding affinity to cannabinoid CB2 receptor2010Journal of medicinal chemistry, Jun-10, Volume: 53, Issue:11
Emerging targets in osteoporosis disease modification.
AID1127493Selectivity ratio of Ki for rat CB1 receptor to Ki for human CB2 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID1706278Agonist activity at CB2R in LPS induced mouse BV2 cells assessed as decrease in IL-1beta secretion at 10 uM preincubated for 30 mins followed by LPS stimulation for 4 hrs by ELISA2020European journal of medicinal chemistry, Dec-15, Volume: 208The endocannabinoid system dual-target ligand N-cycloheptyl-1,2-dihydro-5-bromo-1-(4-fluorobenzyl)-6-methyl-2-oxo-pyridine-3-carboxamide improves disease severity in a mouse model of multiple sclerosis.
AID1167199Displacement of [3H]CP-55,940 from human recombinant CB2R expressed in HEK-293 cells after 90 mins by liquid scintillation counting2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
CB2-selective cannabinoid receptor ligands: synthesis, pharmacological evaluation, and molecular modeling investigation of 1,8-Naphthyridin-2(1H)-one-3-carboxamides.
AID412565Displacement of [3H]CP-55940 from human recombinant CB1 receptor2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Discovery of novel CB2 receptor ligands by a pharmacophore-based virtual screening workflow.
AID1067338Displacement of [3H]CP55,940 from human recombinant CB1 receptor expressed in HEK293 cell membranes after 90 mins2014European journal of medicinal chemistry, Mar-03, Volume: 741,2-Dihydro-2-oxopyridine-3-carboxamides: the C-5 substituent is responsible for functionality switch at CB2 cannabinoid receptor.
AID1601903Antiproliferative activity against Alzheimer's patient derived lymphoblast cells at 5 uM after 72 hrs by MTT assay2019European journal of medicinal chemistry, Mar-15, Volume: 166Indazolylketones as new multitarget cannabinoid drugs.
AID1853227Cytotoxicity against human KNS-42 cells assessed as reduction in cell viability incubated for 72 hrs by PrestoBlue reagent based cell viability assay
AID375661Selectivity ratio of Ki for human recombinant CB2 receptor to Ki for human recombinant CB1 receptor2009Journal of medicinal chemistry, Jun-25, Volume: 52, Issue:12
Rational design, synthesis, and pharmacological properties of new 1,8-naphthyridin-2(1H)-on-3-carboxamide derivatives as highly selective cannabinoid-2 receptor agonists.
AID1167200Selectivity ratio of Ki for human recombinant CB1R expressed in HEK-293 cells to Ki for human recombinant CB2R expressed in HEK-293 cells2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
CB2-selective cannabinoid receptor ligands: synthesis, pharmacological evaluation, and molecular modeling investigation of 1,8-Naphthyridin-2(1H)-one-3-carboxamides.
AID1626199Displacement of [3H]-CP55940 from human CB2 receptor expressed in HEK293 cell membranes after 1 hr by liquid scintillation spectrometric method2016Journal of medicinal chemistry, 07-28, Volume: 59, Issue:14
Chromenopyrazole, a Versatile Cannabinoid Scaffold with in Vivo Activity in a Model of Multiple Sclerosis.
AID537503Displacement of [3H]CP-55940 from CB1 receptor in Sprague-Dawley rat brain membranes after 1 hr by liquid scintillation spectrophotometry2010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor.
AID259197Displacement of [3H]CP-55940 from human CB2 receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Novel 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives as new CB2 cannabinoid receptors agonists: synthesis, pharmacological properties and molecular modeling.
AID1800327CB1 & 2 Binding Assays from Article 10.1021/cb500177c: \\Functionalization of u00DF-Caryophyllene Generates Novel Polypharmacology in the Endocannabinoid System.\\2014ACS chemical biology, Jul-18, Volume: 9, Issue:7
Functionalization of β-caryophyllene generates novel polypharmacology in the endocannabinoid system.
AID1346728Human CB2 receptor (Cannabinoid receptors)1999Bioorganic & medicinal chemistry, Dec, Volume: 7, Issue:12
3-(1',1'-Dimethylbutyl)-1-deoxy-delta8-THC and related compounds: synthesis of selective ligands for the CB2 receptor.
AID1346728Human CB2 receptor (Cannabinoid receptors)2000Expert opinion on investigational drugs, Jul, Volume: 9, Issue:7
Cannabinoid receptor ligands: clinical and neuropharmacological considerations, relevant to future drug discovery and development.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (204)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (0.49)18.2507
2000's46 (22.55)29.6817
2010's118 (57.84)24.3611
2020's39 (19.12)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.26

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 Index29.26 (24.57)
Research Supply Index5.33 (2.92)
Research Growth Index6.24 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.49%)5.53%
Reviews5 (2.44%)6.00%
Case Studies0 (0.00%)4.05%
Observational1 (0.49%)0.25%
Other198 (96.59%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]