Page last updated: 2024-11-07

ly 99335, (3r-cis)-isomer

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 CID132913
CHEMBL ID318723
SCHEMBL ID12013737
MeSH IDM0324672

Synonyms (7)

Synonym
CHEMBL318723 ,
3-((3r,4r)-1,3,4-trimethyl-piperidin-4-yl)-phenol
bdbm50045772
3-(1,3,4-trimethyl-piperidin-4-yl)-phenol
SCHEMBL12013737
69926-34-7
phenol, 3-[(3r,4r)-1,3,4-trimethyl-4-piperidinyl]-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorRattus norvegicus (Norway rat)Ki0.08000.00000.38458.6000AID224574
Mu-type opioid receptorHomo sapiens (human)Ki0.08000.00000.419710.0000AID152067
Kappa-type opioid receptorCavia porcellus (domestic guinea pig)Ki0.83300.00000.20186.4240AID149274; AID223587; AID223596
Kappa-type opioid receptorHomo sapiens (human)Ki0.83300.00000.362410.0000AID148709
Mu-type opioid receptorCavia porcellus (domestic guinea pig)Ki0.08000.00000.27869.0000AID224574
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorHomo sapiens (human)Ke0.02930.00000.24883.0700AID1125178; AID595125
Delta-type opioid receptorHomo sapiens (human)Ke0.68100.00010.69799.0700AID1125180; AID595126
Kappa-type opioid receptorHomo sapiens (human)Ke0.13400.00000.35405.8100AID1125179; AID595127
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (52)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMu-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
sensory perceptionMu-type opioid receptorHomo sapiens (human)
negative regulation of cell population proliferationMu-type opioid receptorHomo sapiens (human)
sensory perception of painMu-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
behavioral response to ethanolMu-type opioid receptorHomo sapiens (human)
positive regulation of neurogenesisMu-type opioid receptorHomo sapiens (human)
negative regulation of Wnt protein secretionMu-type opioid receptorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeMu-type opioid receptorHomo sapiens (human)
calcium ion transmembrane transportMu-type opioid receptorHomo sapiens (human)
cellular response to morphineMu-type opioid receptorHomo sapiens (human)
regulation of cellular response to stressMu-type opioid receptorHomo sapiens (human)
regulation of NMDA receptor activityMu-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayMu-type opioid receptorHomo sapiens (human)
immune responseDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerDelta-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
adult locomotory behaviorDelta-type opioid receptorHomo sapiens (human)
negative regulation of gene expressionDelta-type opioid receptorHomo sapiens (human)
negative regulation of protein-containing complex assemblyDelta-type opioid receptorHomo sapiens (human)
positive regulation of CREB transcription factor activityDelta-type opioid receptorHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationDelta-type opioid receptorHomo sapiens (human)
response to nicotineDelta-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
eating behaviorDelta-type opioid receptorHomo sapiens (human)
regulation of mitochondrial membrane potentialDelta-type opioid receptorHomo sapiens (human)
regulation of calcium ion transportDelta-type opioid receptorHomo sapiens (human)
cellular response to growth factor stimulusDelta-type opioid receptorHomo sapiens (human)
cellular response to hypoxiaDelta-type opioid receptorHomo sapiens (human)
cellular response to toxic substanceDelta-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayDelta-type opioid receptorHomo sapiens (human)
immune responseKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
chemical synaptic transmissionKappa-type opioid receptorHomo sapiens (human)
sensory perceptionKappa-type opioid receptorHomo sapiens (human)
locomotory behaviorKappa-type opioid receptorHomo sapiens (human)
sensory perception of painKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
response to insulinKappa-type opioid receptorHomo sapiens (human)
positive regulation of dopamine secretionKappa-type opioid receptorHomo sapiens (human)
negative regulation of luteinizing hormone secretionKappa-type opioid receptorHomo sapiens (human)
response to nicotineKappa-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
maternal behaviorKappa-type opioid receptorHomo sapiens (human)
eating behaviorKappa-type opioid receptorHomo sapiens (human)
response to estrogenKappa-type opioid receptorHomo sapiens (human)
estrous cycleKappa-type opioid receptorHomo sapiens (human)
response to ethanolKappa-type opioid receptorHomo sapiens (human)
regulation of saliva secretionKappa-type opioid receptorHomo sapiens (human)
behavioral response to cocaineKappa-type opioid receptorHomo sapiens (human)
sensory perception of temperature stimulusKappa-type opioid receptorHomo sapiens (human)
defense response to virusKappa-type opioid receptorHomo sapiens (human)
cellular response to lipopolysaccharideKappa-type opioid receptorHomo sapiens (human)
cellular response to glucose stimulusKappa-type opioid receptorHomo sapiens (human)
positive regulation of p38MAPK cascadeKappa-type opioid receptorHomo sapiens (human)
positive regulation of potassium ion transmembrane transportKappa-type opioid receptorHomo sapiens (human)
response to acrylamideKappa-type opioid receptorHomo sapiens (human)
positive regulation of eating behaviorKappa-type opioid receptorHomo sapiens (human)
conditioned place preferenceKappa-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
G-protein alpha-subunit bindingMu-type opioid receptorHomo sapiens (human)
G protein-coupled receptor activityMu-type opioid receptorHomo sapiens (human)
beta-endorphin receptor activityMu-type opioid receptorHomo sapiens (human)
voltage-gated calcium channel activityMu-type opioid receptorHomo sapiens (human)
protein bindingMu-type opioid receptorHomo sapiens (human)
morphine receptor activityMu-type opioid receptorHomo sapiens (human)
G-protein beta-subunit bindingMu-type opioid receptorHomo sapiens (human)
neuropeptide bindingMu-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor activityDelta-type opioid receptorHomo sapiens (human)
protein bindingDelta-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingDelta-type opioid receptorHomo sapiens (human)
G protein-coupled enkephalin receptor activityDelta-type opioid receptorHomo sapiens (human)
neuropeptide bindingDelta-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor activityKappa-type opioid receptorHomo sapiens (human)
protein bindingKappa-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingKappa-type opioid receptorHomo sapiens (human)
dynorphin receptor activityKappa-type opioid receptorHomo sapiens (human)
neuropeptide bindingKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (23)

Processvia Protein(s)Taxonomy
endosomeMu-type opioid receptorHomo sapiens (human)
endoplasmic reticulumMu-type opioid receptorHomo sapiens (human)
Golgi apparatusMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
axonMu-type opioid receptorHomo sapiens (human)
dendriteMu-type opioid receptorHomo sapiens (human)
perikaryonMu-type opioid receptorHomo sapiens (human)
synapseMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
neuron projectionMu-type opioid receptorHomo sapiens (human)
plasma membraneDelta-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneDelta-type opioid receptorHomo sapiens (human)
dendrite membraneDelta-type opioid receptorHomo sapiens (human)
presynaptic membraneDelta-type opioid receptorHomo sapiens (human)
axon terminusDelta-type opioid receptorHomo sapiens (human)
spine apparatusDelta-type opioid receptorHomo sapiens (human)
postsynaptic density membraneDelta-type opioid receptorHomo sapiens (human)
neuronal dense core vesicleDelta-type opioid receptorHomo sapiens (human)
plasma membraneDelta-type opioid receptorHomo sapiens (human)
neuron projectionDelta-type opioid receptorHomo sapiens (human)
nucleoplasmKappa-type opioid receptorHomo sapiens (human)
mitochondrionKappa-type opioid receptorHomo sapiens (human)
cytosolKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
membraneKappa-type opioid receptorHomo sapiens (human)
sarcoplasmic reticulumKappa-type opioid receptorHomo sapiens (human)
T-tubuleKappa-type opioid receptorHomo sapiens (human)
dendriteKappa-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneKappa-type opioid receptorHomo sapiens (human)
presynaptic membraneKappa-type opioid receptorHomo sapiens (human)
perikaryonKappa-type opioid receptorHomo sapiens (human)
axon terminusKappa-type opioid receptorHomo sapiens (human)
postsynaptic membraneKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
neuron projectionKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID223591Tested for the antagonism of kappa opioid receptor diuresis at a dose of 0.08 mg/kg subcutaneously1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Structure-activity relationships of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for mu- and kappa-opioid receptors.
AID223596Binding affinity towards kappa opioid receptor by displacement of [3H]EKC in guinea pig cortical tissue1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: opioid antagonists with potent anorectant activity.
AID1125186Agonist activity at human mu opioid receptor expressed CHO cells assessed as inhibition of [35S]-GTP[gammaS] binding at 10 uM2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Effect of the 3- and 4-methyl groups on the opioid receptor properties of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines.
AID595126Antagonist activity at human delta opioid receptor expressed in CHO cells assessed as inhibition of DPDPE stimulated [35S]GTPgammaS binding2010ACS medicinal chemistry letters, Oct-14, Volume: 1, Issue:7
1-Substituted 4-(3-Hydroxyphenyl)piperazines Are Pure Opioid Receptor Antagonists.
AID1125191Analgesic activity in mouse assessed as antagonism of U50488-induced antinociception by writhing test2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Effect of the 3- and 4-methyl groups on the opioid receptor properties of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines.
AID152067Binding affinity against Opioid receptor mu 1 using [3H]naloxone as radioligand.1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
N-Substituted 9beta-methyl-5-(3-hydroxyphenyl)morphans are opioid receptor pure antagonists.
AID224715Antagonism of opioid analgesia using a mouse writhing model to block morphine (2.5 mg/kg) induced mu-opioid receptor (subcutaneously dosed)1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Structure-activity relationships of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for mu- and kappa-opioid receptors.
AID595127Antagonist activity at human kappa opioid receptor expressed in CHO cells assessed as inhibition of U69,593 stimulated [35S]GTPgammaS binding2010ACS medicinal chemistry letters, Oct-14, Volume: 1, Issue:7
1-Substituted 4-(3-Hydroxyphenyl)piperazines Are Pure Opioid Receptor Antagonists.
AID223599Antagonist activity towards U50 488 induced kappa opioid receptor by mouse writhing assay at 2.5 mg/kg subcutaneously1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: opioid antagonists with potent anorectant activity.
AID223587Binding affinity towards kappa-opioid receptor by displacement of [3H]-EKC at from guinea pig cortical tissue1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Structure-activity relationships of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for mu- and kappa-opioid receptors.
AID1125178Antagonist activity at human mu opioid receptor expressed CHO cells assessed as inhibition of [35S]-GTP[gammaS] binding2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Effect of the 3- and 4-methyl groups on the opioid receptor properties of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines.
AID1125188Agonist activity at human delta opioid receptor expressed CHO cells assessed as inhibition of [35S]-GTP[gammaS] binding at 10 uM2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Effect of the 3- and 4-methyl groups on the opioid receptor properties of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines.
AID1125179Antagonist activity at human kappa opioid receptor expressed CHO cells assessed as inhibition of [35S]-GTP[gammaS] binding2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Effect of the 3- and 4-methyl groups on the opioid receptor properties of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines.
AID224576Antagonistic activity towards morphine induced mu-opioid receptor by mouse writhing assay at 1.25 mg/kg subcutaneously1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: opioid antagonists with potent anorectant activity.
AID224587Binding affinity towards mu-opioid receptor by the displacement of [3H]Nal in rat brain homogenates1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: opioid antagonists with potent anorectant activity.
AID176827Tested for concentration required to reduce the food consumption by 20 % subcutaneously1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: opioid antagonists with potent anorectant activity.
AID149274Binding affinity was determined against Opioid receptor kappa 1
using [3H]ethylketocyclazocine as radioligand
1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
N-substituted octahydro-4a-(3-hydroxyphenyl)-10a-methyl-benzo[g]isoquinolines are opioid receptor pure antagonists.
AID223589Antagonism of opioid analgesia using a mouse writhing model to block U-50,488 (2.5 mg/kg) induced kappa-opioid receptor subcutaneously1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Structure-activity relationships of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for mu- and kappa-opioid receptors.
AID1125180Antagonist activity at human delta opioid receptor expressed CHO cells assessed as inhibition of [35S]-GTP[gammaS] binding2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Effect of the 3- and 4-methyl groups on the opioid receptor properties of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines.
AID148709Binding affinity against Opioid receptor kappa 1 using [3H]ethylketocyclazocine as radioligand.1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
N-Substituted 9beta-methyl-5-(3-hydroxyphenyl)morphans are opioid receptor pure antagonists.
AID223601Antagonism of bremazocine induced kappa receptor diuresis in rats at a concentration of 0.08 mg/kg subcutaneously1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: opioid antagonists with potent anorectant activity.
AID1125187Agonist activity at human kappa opioid receptor expressed CHO cells assessed as inhibition of [35S]-GTP[gammaS] binding at 10 uM2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Effect of the 3- and 4-methyl groups on the opioid receptor properties of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines.
AID1125190Analgesic activity in mouse assessed as antagonism of morphine-induced antinociception by writhing test2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Effect of the 3- and 4-methyl groups on the opioid receptor properties of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines.
AID224718Binding affinity towards mu opioid receptor by displacement of [3H]NAL from rat brain homogenates1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Structure-activity relationships of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for mu- and kappa-opioid receptors.
AID224574Binding affinity was determined against Mu opioid receptor using [3H]-Naltrexone as radioligand1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
N-substituted octahydro-4a-(3-hydroxyphenyl)-10a-methyl-benzo[g]isoquinolines are opioid receptor pure antagonists.
AID595125Antagonist activity at human mu opioid receptor expressed in CHO cells assessed as inhibition of DAMGO stimulated [35S]GTPgammaS binding2010ACS medicinal chemistry letters, Oct-14, Volume: 1, Issue:7
1-Substituted 4-(3-Hydroxyphenyl)piperazines Are Pure Opioid Receptor Antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (66.67)18.2507
2000's0 (0.00)29.6817
2010's2 (33.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.43

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

MetricThis Compound (vs All)
Research Demand Index12.43 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.43)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]