Page last updated: 2024-12-04

3-methoxymorphinan

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

Description

3-methoxymorphinan: dextromethorphan metabolite; RN & N1 from 9th CI Form Index; RN given refers to cpd without isomeric designation; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1671
CHEMBL ID297313
MeSH IDM0092000
PubMed CID5484286
CHEMBL ID1623871
SCHEMBL ID508549
MeSH IDM0092000

Synonyms (27)

Synonym
3-methoxymorphinan
CHEMBL297313
ILNSWVUXAPSPEH-UHFFFAOYSA-N
PD034318
morphinan, 3-methoxy-
1531-25-5
LOPAC0_000864
NCGC00162284-01
NCGC00162284-02
CCG-204946
unii-497wv2ey4t
497wv2ey4t ,
einecs 216-240-6
norlevomethorphan
3-methoxymorphinan, (-)-
(-)-3-methoxymorphinan
ILNSWVUXAPSPEH-USXIJHARSA-N
(+)-3-methoxy-morphinan
SCHEMBL508549
CHEMBL1623871 ,
bdbm50505665
Q4634166
(1r,9r,10r)-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
SDCCGSBI-0050839.P002
(1s,9s,10r)-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
(1r,9r,10r)-4-methoxy-17-azatetracyclo[7.5.3.0?,??.0?,?]heptadeca-2(7),3,5-triene
PD052832

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"5 mg/kg in a crossover fashion in a two-sequence pharmacokinetic study with a wash-out period of at least 7 days."( A urine metabolic ratio of dextromethorphan and 3-methoxymorphinan as a probe for CYP3A activity and prediction of cyclosporine clearance in healthy volunteers.
Fleckenstein, LL; Ku, YM; Min, DI; Vichiendilokkul, A, 1999
)
0.56

Dosage Studied

ExcerptRelevanceReference
"Ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC-QToF-MS) analysis of dextromethorphan (DXM) and its metabolites-dextrorphan, 3-methoxymorphinan (3-MEM) and 3-hydroxymorphinan-in skeletal remains of rats exposed to DXM under different dosing patterns is described."( Analysis of Dextromethorphan and Three Metabolites in Decomposed Skeletal Tissues by UPLC-QToF-MS: Comparison of Acute and Repeated Drug Exposures.
Cornthwaite, HM; McDonald, CS; Watterson, JH, 2019
)
0.71
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
USP1 protein, partialHomo sapiens (human)Potency100.00000.031637.5844354.8130AID504865
arylsulfatase AHomo sapiens (human)Potency8.49211.069113.955137.9330AID720538
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency14.12540.035520.977089.1251AID504332
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa)Homo sapiens (human)Potency58.47890.016525.307841.3999AID602332
chromobox protein homolog 1Homo sapiens (human)Potency39.81070.006026.168889.1251AID488953
flap endonuclease 1Homo sapiens (human)Potency0.13370.133725.412989.1251AID588795
Ataxin-2Homo sapiens (human)Potency17.78280.011912.222168.7989AID588378
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 22 member 1 Homo sapiens (human)IC50 (µMol)10.00000.21005.553710.0000AID1526751
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processSolute carrier family 22 member 1 Homo sapiens (human)
neurotransmitter transportSolute carrier family 22 member 1 Homo sapiens (human)
serotonin transportSolute carrier family 22 member 1 Homo sapiens (human)
establishment or maintenance of transmembrane electrochemical gradientSolute carrier family 22 member 1 Homo sapiens (human)
organic cation transportSolute carrier family 22 member 1 Homo sapiens (human)
quaternary ammonium group transportSolute carrier family 22 member 1 Homo sapiens (human)
prostaglandin transportSolute carrier family 22 member 1 Homo sapiens (human)
monoamine transportSolute carrier family 22 member 1 Homo sapiens (human)
putrescine transportSolute carrier family 22 member 1 Homo sapiens (human)
spermidine transportSolute carrier family 22 member 1 Homo sapiens (human)
acetylcholine transportSolute carrier family 22 member 1 Homo sapiens (human)
dopamine transportSolute carrier family 22 member 1 Homo sapiens (human)
norepinephrine transportSolute carrier family 22 member 1 Homo sapiens (human)
thiamine transportSolute carrier family 22 member 1 Homo sapiens (human)
xenobiotic transportSolute carrier family 22 member 1 Homo sapiens (human)
epinephrine transportSolute carrier family 22 member 1 Homo sapiens (human)
serotonin uptakeSolute carrier family 22 member 1 Homo sapiens (human)
norepinephrine uptakeSolute carrier family 22 member 1 Homo sapiens (human)
thiamine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
metanephric proximal tubule developmentSolute carrier family 22 member 1 Homo sapiens (human)
purine-containing compound transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
dopamine uptakeSolute carrier family 22 member 1 Homo sapiens (human)
monoatomic cation transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
transport across blood-brain barrierSolute carrier family 22 member 1 Homo sapiens (human)
(R)-carnitine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
acyl carnitine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
spermidine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
cellular detoxificationSolute carrier family 22 member 1 Homo sapiens (human)
xenobiotic transport across blood-brain barrierSolute carrier family 22 member 1 Homo sapiens (human)
negative regulation of receptor internalizationAtaxin-2Homo sapiens (human)
regulation of translationAtaxin-2Homo sapiens (human)
RNA metabolic processAtaxin-2Homo sapiens (human)
P-body assemblyAtaxin-2Homo sapiens (human)
stress granule assemblyAtaxin-2Homo sapiens (human)
RNA transportAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (22)

Processvia Protein(s)Taxonomy
acetylcholine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
neurotransmitter transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
dopamine:sodium symporter activitySolute carrier family 22 member 1 Homo sapiens (human)
norepinephrine:sodium symporter activitySolute carrier family 22 member 1 Homo sapiens (human)
protein bindingSolute carrier family 22 member 1 Homo sapiens (human)
monoamine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
secondary active organic cation transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
organic anion transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
organic cation transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
prostaglandin transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
pyrimidine nucleoside transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
thiamine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
putrescine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
spermidine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
quaternary ammonium group transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
toxin transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
identical protein bindingSolute carrier family 22 member 1 Homo sapiens (human)
xenobiotic transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
(R)-carnitine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
RNA bindingAtaxin-2Homo sapiens (human)
epidermal growth factor receptor bindingAtaxin-2Homo sapiens (human)
protein bindingAtaxin-2Homo sapiens (human)
mRNA bindingAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
basal plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
membraneSolute carrier family 22 member 1 Homo sapiens (human)
basolateral plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
apical plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
lateral plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
presynapseSolute carrier family 22 member 1 Homo sapiens (human)
cytoplasmAtaxin-2Homo sapiens (human)
Golgi apparatusAtaxin-2Homo sapiens (human)
trans-Golgi networkAtaxin-2Homo sapiens (human)
cytosolAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
membraneAtaxin-2Homo sapiens (human)
perinuclear region of cytoplasmAtaxin-2Homo sapiens (human)
ribonucleoprotein complexAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID196181The compound was tested for anticonvulsive activity expressed as seizure score after 4 hr of injection of kainic acid (10 mg/kg) and the drug at the dose of 20 mg/Kg in 15 rats2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
Anticonvulsant effects of new morphinan derivatives.
AID196182The compound was tested for anticonvulsive activity expressed as seizure score after 4 hr of injection of kainic acid (10 mg/kg) and the drug at the dose of 40 mg/Kg in 15 rats2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
Anticonvulsant effects of new morphinan derivatives.
AID184524Effect was expressed as mortality after injection of kainic acid (10 mg/kg) and the drug at the dose of 20 mg/Kg after 48 hr out of 19 animals2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
Anticonvulsant effects of new morphinan derivatives.
AID170083The compound was examined for circling behavior (marginal activity) using automated videotracking system 30 min after intraperitoneal injection at the dose of 40 mg/Kg in 12 rats2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
Anticonvulsant effects of new morphinan derivatives.
AID170082The compound was examined for circling behavior (marginal activity) using automated videotracking system 30 min after intraperitoneal injection at the dose of 20 mg/Kg in 12 rats2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
Anticonvulsant effects of new morphinan derivatives.
AID184525Effect was expressed as mortality after injection of kainic acid (10 mg/kg) and the drug at the dose of 40 mg/Kg after 48 hr2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
Anticonvulsant effects of new morphinan derivatives.
AID1508629Cell Viability qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID1508627Counterscreen qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: GLuc-NoTag assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1508628Confirmatory qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1526751Inhibition of human OCT1 expressed in HEK293 cells assessed as reduction in ASP+ substrate uptake by microplate reader based analysis2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID1526752Passive membrane permeability by LC-MS/MS analysis based PAMPA2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID1526732Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake at 0.1 uM incubated for 2 mins by LC-MS/MS analysis relative to control empty vector transfected cells2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID1526731Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake at 0.05 uM incubated for 2 mins by LC-MS/MS analysis relative to control empty vector transfected cells2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID1526733Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake at 0.5 uM incubated for 2 mins by LC-MS/MS analysis relative to control empty vector transfected cells2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID1526734Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake at 0.05 to 0.5 uM incubated for 2 mins in presence of 2 mM MPP+ by LC-MS/MS analysis relative to control empty vector transfected cells2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (39)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.56)18.7374
1990's11 (28.21)18.2507
2000's14 (35.90)29.6817
2010's10 (25.64)24.3611
2020's3 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.15

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 Index25.15 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index5.51 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.15)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (21.88%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other25 (78.13%)84.16%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]