Page last updated: 2024-11-08

6 beta-hydroxynaltrexone

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

Cross-References

ID SourceID
PubMed CID5486554
CHEMBL ID140278
CHEBI ID192658
SCHEMBL ID679700
MeSH IDM0055894

Synonyms (43)

Synonym
morphinan-3,6alpha,14-triol, 17-(cyclopropylmethyl)-4,5alpha-epoxy-
alpha-naltrexol
en 2260
17-(cyclopropylmethyl)-4,5alpha-epoxymorphinan-3,6alpha,14-triol
NCGC00165851-01
6beta-naltrexone
6alpha-naltrexone
6beta-naltrexol
CHEMBL140278 ,
bdbm50001709
4-cyclopropylmethyl-(13r)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-triene-10,14,17-triol
naltrexone-6-beta-ol
(4r,4as,7r,7ar,12bs)-3-(cyclopropylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzouro[3,2-e]isoquinoline-4a,7,9-triol
20410-98-4
CHEBI:192658
6alpha-naltrexol
naltrexol
n-cyclopropylmethyl-7,8-dihydro-14-hydroxynorisomorphine
beta-naltrexol
6alpha-hydroxynaltrexone
49625-89-0
unii-j0w963m37t
j0w963m37t ,
morphinan-3,6,14-triol, 17-(cyclopropylmethyl)-4,5-epoxy-, (5alpha,6beta)-
17-(cyclopropylmethyl)-4,5-epoxymorphinan-3,6beta,14-triol
6beta-hydroxynaltrexone
aiko-150
6-alpha-naltrexol
17-cyclopropylmethyl-4,5alpha-epoxy-3,6beta,14-trihydroxymorphinan
JLVNEHKORQFVQJ-PYIJOLGTSA-N
SCHEMBL679700
6.beta.-naltrexol
.beta.-naltrexol
morphinan-3,6,14-triol, 17-(cyclopropylmethyl)-4,5-epoxy-, (5.alpha.,6.beta.)-
6.beta.-hydroxynaltrexone
DTXSID80197942
6-beta-naltrexol hcl
6-|a-naltrexol hcl
Q19598102
(4r,4as,7r,7ar,12bs)-3-(cyclopropylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
6?-naltrexol
6-beta-naltrexol, 1mg/ml in methanol
morphinan-3,6,14-triol, 17-(cyclopropylmethyl)-4,5-epoxy-, (5?,6?)-; (5?,6?)-17-(cyclopropylmethyl)-4,5-epoxymorphinan-3,6,14-triol; 17-(cyclopropylmethyl)-4,5?-epoxy-3,14-dihydroxymorphinan-6?-ol; 6?-hydroxynaltrexone; 6?-naltrexol; ?-naltrexol
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenanthrenesAny benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.
[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 (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta-type opioid receptorMus musculus (house mouse)IC50 (µMol)0.00970.00010.729810.0000AID148621; AID148624
Delta-type opioid receptorRattus norvegicus (Norway rat)IC50 (µMol)0.02300.00030.38877.0000AID149626
Mu-type opioid receptorHomo sapiens (human)IC50 (µMol)0.00830.00010.813310.0000AID148621; AID148624
Mu-type opioid receptorHomo sapiens (human)Ki0.00020.00000.419710.0000AID410718
Delta-type opioid receptorHomo sapiens (human)IC50 (µMol)0.01990.00020.75218.0140AID148621; AID148624; AID149626; AID149750
Delta-type opioid receptorHomo sapiens (human)Ki0.05300.00000.59789.9300AID410719
Kappa-type opioid receptorCavia porcellus (domestic guinea pig)IC50 (µMol)0.00810.00030.71237.0700AID147958; AID148692
Kappa-type opioid receptorHomo sapiens (human)IC50 (µMol)0.00830.00001.201110.0000AID148621; AID148624
Kappa-type opioid receptorHomo sapiens (human)Ki0.00050.00000.362410.0000AID410720
Mu-type opioid receptorCavia porcellus (domestic guinea pig)IC50 (µMol)0.00130.00020.660310.0000AID141490; AID148992
[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)
Mu-type opioid receptorHomo sapiens (human)EC50 (µMol)0.00120.00000.32639.4000AID694465
[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 (19)

Assay IDTitleYearJournalArticle
AID147960Inhibition of opioid receptor kappa by displacing 0.5 nM [3H]bremazocine in guinea pig brain membrane1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
O3-(2-carbomethoxyallyl) ethers of opioid ligands derived from oxymorphone, naltrexone, etorphine, diprenorphine, norbinaltorphimine, and naltrindole. Unexpected O3-dealkylation in the opioid radioligand displacement assay.
AID147958Displacement of 0.5 nM [3H]bremazocine from guinea pig brain membrane opioid receptor kappa with 100 nM DAGO and 100 nM DPDPE1992Journal of medicinal chemistry, Jun-26, Volume: 35, Issue:13
Electrophilic opioid ligands. Oxygen tethered alpha-methylene-gamma-lactone, acrylate, isothiocyanate, and epoxide derivatives of 6 beta-naltrexol.
AID694465Inverse agonist activity at human recombinant mu opioid receptor expressed in CHO cells after 3 hrs by [35S]GTPgammaS binding assay2012Bioorganic & medicinal chemistry letters, Nov-15, Volume: 22, Issue:22
An efficient synthesis of 3-OBn-6β,14-epoxy-bridged opiates from naltrexone and identification of a related dual MOR inverse agonist/KOR agonist.
AID149750Tested for the binding affinity against the Delta opioid receptor in guinea pig brain using [3H]DPDPE1994Journal of medicinal chemistry, Dec-09, Volume: 37, Issue:25
Synthesis and opioid receptor affinity of a series of aralkyl ethers of 6 alpha- and 6 beta-naltrexol.
AID410718Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID149630Inhibition of Opioid receptor delta 1 by displacing 1 nM [3H]DPDPE in guinea pig brain membrane1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
O3-(2-carbomethoxyallyl) ethers of opioid ligands derived from oxymorphone, naltrexone, etorphine, diprenorphine, norbinaltorphimine, and naltrindole. Unexpected O3-dealkylation in the opioid radioligand displacement assay.
AID410721Ratio of Ki for human mu opioid receptor to Ki for human kappa opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID148692Tested for the binding affinity against the Kappa opioid receptor in guinea pig brain using [3H]U-695931994Journal of medicinal chemistry, Dec-09, Volume: 37, Issue:25
Synthesis and opioid receptor affinity of a series of aralkyl ethers of 6 alpha- and 6 beta-naltrexol.
AID694466Inverse agonist activity at human recombinant mu opioid receptor expressed in CHO cells after 3 hrs by [35S]GTPgammaS binding assay relative to KC-2-0092012Bioorganic & medicinal chemistry letters, Nov-15, Volume: 22, Issue:22
An efficient synthesis of 3-OBn-6β,14-epoxy-bridged opiates from naltrexone and identification of a related dual MOR inverse agonist/KOR agonist.
AID148475Inhibition of total opioid receptor by displacing 0.5 nM [3H]bremazocine in guinea pig brain membrane1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
O3-(2-carbomethoxyallyl) ethers of opioid ligands derived from oxymorphone, naltrexone, etorphine, diprenorphine, norbinaltorphimine, and naltrindole. Unexpected O3-dealkylation in the opioid radioligand displacement assay.
AID141490Tested for the binding affinity against the Mu opioid receptor in guinea pig brain using [3H]-DAMGO1994Journal of medicinal chemistry, Dec-09, Volume: 37, Issue:25
Synthesis and opioid receptor affinity of a series of aralkyl ethers of 6 alpha- and 6 beta-naltrexol.
AID149626Inhibition of [3H]DPDPE binding to guinea pig brain membrane Opioid receptor delta 1 at 1.0 nM1992Journal of medicinal chemistry, Jun-26, Volume: 35, Issue:13
Electrophilic opioid ligands. Oxygen tethered alpha-methylene-gamma-lactone, acrylate, isothiocyanate, and epoxide derivatives of 6 beta-naltrexol.
AID148621Tested for the binding affinity against the opioid receptor in guinea pig brain using [3H]bremazocine1994Journal of medicinal chemistry, Dec-09, Volume: 37, Issue:25
Synthesis and opioid receptor affinity of a series of aralkyl ethers of 6 alpha- and 6 beta-naltrexol.
AID410722Ratio of Ki for human delta opioid receptor to Ki for human kappa opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID410720Displacement of [3H]U69593 form human kappa opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID148624Inhibition of 0.5 nM [3H]bremazocine binding to guinea pig brain membrane opioid receptors1992Journal of medicinal chemistry, Jun-26, Volume: 35, Issue:13
Electrophilic opioid ligands. Oxygen tethered alpha-methylene-gamma-lactone, acrylate, isothiocyanate, and epoxide derivatives of 6 beta-naltrexol.
AID148993Inhibition of opioid receptor mu by displacing 1 nM [3H]DAGO in guinea pig brain membrane1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
O3-(2-carbomethoxyallyl) ethers of opioid ligands derived from oxymorphone, naltrexone, etorphine, diprenorphine, norbinaltorphimine, and naltrindole. Unexpected O3-dealkylation in the opioid radioligand displacement assay.
AID410719Displacement of [3H]Naltrindole form human delta opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID148992inhibition of 1.0 nM [3H]- DAGO binding to guinea pig brain membrane opioid receptor mu1992Journal of medicinal chemistry, Jun-26, Volume: 35, Issue:13
Electrophilic opioid ligands. Oxygen tethered alpha-methylene-gamma-lactone, acrylate, isothiocyanate, and epoxide derivatives of 6 beta-naltrexol.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (60.00)18.2507
2000's1 (20.00)29.6817
2010's1 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]