Page last updated: 2024-12-04

normetanephrine

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

Description

Normetanephrine: A methylated metabolite of norepinephrine that is excreted in the urine and found in certain tissues. It is a marker for tumors. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1237
CHEMBL ID774
CHEBI ID89951
SCHEMBL ID137755
MeSH IDM0014988

Synonyms (56)

Synonym
N111 ,
LOPAC0_000858
NCGC00162280-01
E0A31F1E-8030-4E7F-B27B-71710BF11CE5
normetadrenaline
benzenemethanol, alpha-(aminomethyl)-4-hydroxy-3-methoxy-
NCGC00015746-03
97-31-4
3-methoxynoradrenaline
normetanephrine
(+/-)-normetanephrine
chebi:89951 ,
CHEMBL774
dl-normetanephrine
4-(2-amino-1-hydroxyethyl)-2-methoxyphenol
AKOS000123554
0j45de6b88 ,
unii-0j45de6b88
CCG-204941
NCGC00015746-02
gtpl6643
3-methoxy-4,.beta.-dihydroxyphenylethylamine
3-o-methylnoradrenaline
.alpha.-(aminomethyl)-4-hydroxy-3-methoxybenzenemethanol
3-o-methylarterenol
vanillyl alcohol, .alpha.-(aminomethyl)-
4-hydroxy-3-methoxy-.alpha.-(aminomethyl)benzyl alcohol
3-o-methylnorepinephrine
3-methoxy-4-hydroxyphenylethanolamine
4-hydroxy-3-methoxyphenethanolamine
.alpha.-(aminomethyl)vanillyl alcohol
normetanephrine [mi]
3-methoxynorepinephrine
dl-m-o-methylnorepinephrine
dl-3-o-methylnorepinephrine
normetanephrine, (+/-)-
SCHEMBL137755
3-methoxy-4-hydroxy-phenylethanolamine
benzenemethanol, .alpha.-(aminomethyl)-4-hydroxy-3-methoxy-
2-amino-1-(4-hydroxy-3-methoxyphenyl)ethanol
alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol
dl-n-normetanephrine
m-o-methylnorepinephrine
(+/-)-alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol
o-methylnoradrenaline
3-methoxy-noradrenaline
3-o-methyl-noradrenaline
Q517109
4-[(1rs)-2-amino-1-hydroxyethyl]-2-methoxyphenol
DTXSID70861701
SDCCGSBI-0050834.P002
NCGC00015746-05
MS-22981
HY-113517
CS-0062498
EN300-1699600

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
"5 g of levodopa daily for up to six months and in 30 patients receiving levodopa (800-1,000 mg) combined with a dopa decarboxylase inhibitor, benserazide (200-250 mg)."( Urinary excretion of monoamines and their metabolites in patients with Parkinson's disease. Response to long-term treatment with levodopa alone or in combination with a dopa decarboxylase inhibitor and clinical correlations.
Rinne, UK; Siirtola, T; Sonninen, V, 1975
)
0.25
" In this work, a UPLC/ MS/MS-based method combined with a diethyl labeling technique was developed for simultaneous determination of a panel of monoamines in rat prefrontal cortex microdialysates."( Diethylation labeling combined with UPLC/MS/MS for simultaneous determination of a panel of monoamine neurotransmitters in rat prefrontal cortex microdialysates.
El-Kattan, AF; Fountain, S; Ji, C; Kozak, R; Lepsy, C; Li, W; Ren, XD, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
" Dose-response curves for acetylcholine with and without dopamine, isoprenaline, phenylephrine and noradrenaline were obtained."( The depressor effect of dopamine on the electrical and mechanical activities of cat small intestine.
Okawa, H; Wantanabe, M, 1975
)
0.25
" The dose-response curves for the two last-mentioned dopamine metabolites closely follow those for MAO A and dopamine-deaminating activity, whether clorgyline or deprenil was used as MAO inhibitor."( Preferential deamination of dopamine by an A type monoamine oxidase in rat brain.
Delini-Stula, A; Maître, L; Waldmeier, PC, 1976
)
0.26
"The dosage of urinary catecholamines and their metabolites is a main element of diagnosis in the research of a pheochromocytoma in patients with high blood pressure."( [Absence of labetalol interference on urine metanephrine determination in hypertensive patients].
Billaud, EM; Girerd, X; Laurent, S; Ropers, J; Safar, M; Safavian, A; Sorrel-Dejerine, A, 1992
)
0.28
" After 4 days oral treatment, both verapamil and nisoldipine significantly attenuated the responses to angiotensin II with three- to fivefold rightward shifts of the mean pressor dose-response curves."( Effect of calcium channel blockers on adrenergic and nonadrenergic vascular responses in man.
Elliott, HL; Meredith, PA; Pasanisi, F; Reid, JL; Sumner, DJ,
)
0.13
" Type I sensitizations are appropriately described by determining the dose-ratio (horizontal shift of the dose-response curve) and type II sensitizations by assessing the change in the magnitude of the response."( A new approach to the measurement and classification of forms of supersensitivity of autonomic effector responses.
Kalsner, S, 1974
)
0.25
" Effects of TCP on concentrations of DA and NA varied, depending on the brain area investigated and the dosage used."( Regional concentrations of cerebral amines: effects of tranylcypromine and phenelzine.
Baker, GB; Calverly, DG; Dewhurst, WG; McKim, RH, 1983
)
0.27
" TYR PD30 increased significantly with desipramine dosing (p<0."( Duloxetine increases serotonin and norepinephrine availability in healthy subjects: a double-blind, controlled study.
Bieck, PR; Bymaster, FP; Chalon, SA; Granier, LA; Hirth, C; Joliat, MJ; Potter, WZ; Vandenhende, FR, 2003
)
0.32
" Corticosterone failed to re-establish extinguished preference alone but produced a leftward shift in the dose-response curve for cocaine-primed reinstatement."( Corticosterone Potentiation of Cocaine-Induced Reinstatement of Conditioned Place Preference in Mice is Mediated by Blockade of the Organic Cation Transporter 3.
Ambrosius, T; Baker, DA; Derricks, O; Gasser, PJ; Kurtoglu, B; Mantsch, JR; McReynolds, JR; Nino, B; Taylor, A; Vranjkovic, O; Wheeler, RA, 2017
)
0.46
"018), in a dose-response manner across increasing urinary normetanephrine quartile categories (P for trend = 0."( Higher sympathetic activity as a risk factor for skeletal deterioration in pheochromocytoma.
Kim, BJ; Kim, JS; Koh, JM; Kwak, MK; Lee, SH, 2018
)
0.73
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
catecholamine4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] and derivatives formed by substitution.
[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]

Pathways (9)

PathwayProteinsCompounds
Tyrosine Metabolism1657
Alkaptonuria1657
Hawkinsinuria1657
Tyrosinemia Type I1657
Disulfiram Action Pathway2366
Tyrosinemia, Transient, of the Newborn1657
Dopamine beta-Hydroxylase Deficiency1657
Monoamine Oxidase-A Deficiency (MAO-A)1657
22q11.2 copy number variation syndrome228

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thioredoxin reductaseRattus norvegicus (Norway rat)Potency1.00000.100020.879379.4328AID588453
GLS proteinHomo sapiens (human)Potency2.23870.35487.935539.8107AID624146
arylsulfatase AHomo sapiens (human)Potency11.99551.069113.955137.9330AID720538
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency15.84890.035520.977089.1251AID504332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID588378qHTS for Inhibitors of ATXN expression: Validation
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.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
AID215613Dissociation constant against a series of agonists of membranes of the turkey erythrocyte containing mainly Beta adrenergic receptor was determined1982Journal of medicinal chemistry, Dec, Volume: 25, Issue:12
Correlation between affinity toward adrenergic receptors and approximate electrostatic potentials of phenylethylamine derivatives. 1. Effects of the side chain.
AID230399Ratio of maximum contraction of rat aorta elicited versus that elicited by noradrenaline (defined as intrinsic activity)1980Journal of medicinal chemistry, Jul, Volume: 23, Issue:7
Synthesis and structure-activity relationships among alpha-adrenergic receptor agonists of the phenylethanolamine type.
AID33254Binding affinity to alpha adrenergic receptors in rat aorta1980Journal of medicinal chemistry, Jul, Volume: 23, Issue:7
Synthesis and structure-activity relationships among alpha-adrenergic receptor agonists of the phenylethanolamine type.
AID386623Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,245)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990854 (68.59)18.7374
1990's92 (7.39)18.2507
2000's84 (6.75)29.6817
2010's152 (12.21)24.3611
2020's63 (5.06)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 58.41

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index58.41 (24.57)
Research Supply Index7.21 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index100.24 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (58.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials40 (3.06%)5.53%
Reviews37 (2.83%)6.00%
Case Studies70 (5.35%)4.05%
Observational4 (0.31%)0.25%
Other1,157 (88.46%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]