Page last updated: 2024-11-04

3-methoxytyramine

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

Description

3-methoxytyramine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3-methoxytyramine : A monomethoxybenzene that is dopamine in which the hydroxy group at position 3 is replaced by a methoxy group. It is a metabolite of the neurotransmitter dopamine and considered a potential biomarker of pheochromocytomas and paragangliomas. [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 CID1669
CHEMBL ID1160785
CHEBI ID1582
SCHEMBL ID68386
MeSH IDM0042057

Synonyms (73)

Synonym
AC-6711
5-(2-aminoethyl)guaiacol
phenol, 4-(2-aminoethyl)-2-methoxy-
3-methoxy-4-hydroxyphenylethyl amine
methoxytyramine
NCGC00015674-01
lopac-m-4251
LOPAC0_000796
C05587
554-52-9
3-methoxytyramine
NCGC00162257-02
NCGC00162257-01
0F899116-F44F-422B-B36A-7F12600FCCBD
tyramine, 3-methoxy-
3-o-methyldopamine
AKOS000161280
4-(2-amino-ethyl)-2-methoxy-phenol
L000765
3-methoxy-4-hydroxyphenethylamine
4-(2-aminoethyl)-2-methoxyphenol
chebi:1582 ,
CHEMBL1160785
A8025
jch2767edp ,
unii-jch2767edp
ec 611-267-3
3-mt
4-(2-aminoethyl)-2-methoxy-phenol
BMSE000929
BMSE000958
CCG-204880
bdbm85380
cas_1477-68-5
mt-3
cid_11957621
4-hydroxy-3-methoxyphenylethylamine
NCGC00015674-02
NCGC00015674-03
gtpl6642
SCHEMBL68386
hydroxy-3-methoxyphenethylamine, 4-
2-methoxy-4-(2-aminoethyl)phenol
4-hydroxy-3-methoxy-.beta.-phenethylamine
homovanillylamine
4-hydroxy-3-methoxy-2-phenethylamine
3-methoxy-p-tyramine
dopamine impurity b [ep impurity]
guaiacol, 4-(2-aminoethyl)-
4-hydroxy-3-methoxyphenethylamine
homovanillinamine
2-(4-hydroxy-3-methoxyphenyl)ethylamine
dopamine hydrochloride impurity b [ep impurity]
2-(4-hydroxy-3-methoxyphenyl)-ethylamine
2-(4-hydroxy-3-methoxy-phenyl)-ethylamine
4-(2-aminoethyl)-2-methoxyphenol #
Q-102400
mfcd00060621
3-mt . hcl;3-o-methyldopamine . hcl
CS-0028515
HY-103638A
A870191
FT-0711461
DTXSID40862189
Q4634167
FS-6018
4-(2-amino-ethyl)-2-methoxy-phenol controlled drug class a schedule 1
EN300-66666
AMY5037
3-methoxytyramine . hcl
A1-42513
4-(2-aminoethyl)-2-methoxyphenol;4-(2-amino-ethyl)-2-methoxy-phenol
PD046228

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Our findings suggest that the toxic effects of MPP+ on dopaminergic terminals are not mediated through a direct interaction with the NMDA subtype of glutamate receptor, but with the AMPA-kainate subtype."( The non-NMDA glutamate receptor antagonists 6-cyano-7-nitroquinoxaline-2,3-dione and 2,3-dihydroxy-6-nitro-7-sulfamoylbenzo(f)quinoxaline, but not NMDA antagonists, block the intrastriatal neurotoxic effect of MPP+.
Cano, J; Machado, A; Merino, M; Vizuete, ML, 1999
)
0.3
" The dyskinesia develops over a period of exposure to L-dopa and is related to the dosage, therefore, the cause may involve inductive changes that produce toxic levels of metabolites, interfering with dopamine (DA) neurotransmission."( Effects of dopamine metabolites on locomotor activities and on the binding of dopamine: relevance to the side effects of L-dopa.
Charlton, CG; Crowell, B, 2000
)
0.31
"L-3,4-Dihydroxyphenylalanine (L-DOPA) is a common and effective treatment for Parkinson's disease, but dyskinesia continues to be a serious adverse effect with chronic use."( Behavioral activity and stereotypy in rats induced by L-DOPA metabolites: a possible role in the adverse effects of chronic L-DOPA treatment of Parkinson's disease.
Akiyama, A; Nakazato, T, 2002
)
0.31

Compound-Compound Interactions

ExcerptReferenceRelevance
"The effect of amphetamine sulfate (AMPH) on beta-phenylethylamine (PEA) and 3-methoxytyramine (3MT) levels in the rat frontal and cingulate cortices, the nucleus accumbens, and the striatum were evaluated after the administration of either cocaine or reserpine alone and in combination with AMPH."( Effects of the administration of amphetamine, either alone or in combination with reserpine or cocaine, on regional brain beta-phenylethylamine and dopamine release.
Karoum, F; Mosnaim, AD; Wolf, ME,
)
0.36
" Dilution of propionic anhydride 1:4 (v/v) in acetonitrile in combination with 50 μL of plasma resulted in the highest mass spectrometric response."( In Matrix Derivatization Combined with LC-MS/MS Results in Ultrasensitive Quantification of Plasma Free Metanephrines and Catecholamines.
Bischoff, R; de Jong, WHA; Eijkelenkamp, K; Kema, IP; van der Ley, CP; van Faassen, M, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
") also decreased basal cGMP levels in mouse cerebellum for up to 3 h, a result suggesting brain bioavailability and a long duration of NMDA receptor antagonism in vivo."( Neurochemical interactions of competitive N-methyl-D-aspartate antagonists with dopaminergic neurotransmission and the cerebellar cyclic GMP system: functional evidence for a phasic glutamatergic control of the nigrostriatal dopaminergic pathway.
Cler, JA; Contreras, PC; Emmett, MR; Farah, JM; Iyengar, S; Mick, SJ; Rao, TS; Wood, PL, 1991
)
0.28
" These findings support the notion that tolcapone has the ability to enhance striatal dopamine neurotransmission by increasing L-dopa bioavailability through peripheral and central inhibition of L-dopa O-methylation, as well as by blocking the central conversion of dopamine into 3-methoxytyramine."( Effects of tolcapone, a novel catechol-O-methyltransferase inhibitor, on striatal metabolism of L-dopa and dopamine in rats.
Da Prada, M; Napolitano, A; Zürcher, G, 1995
)
0.47
" On the contrary, the [3H]mazindol tracer dose induced a marked labelling of the noradrenaline uptake complex in cerebellum; its prevention by desipramine (5 mg/kg) increased simultaneously the cerebral bioavailability and thereby the striatal labelling of the dopamine transporter."( Pharmacological modifications of dopamine transmission do not influence the striatal in vivo binding of [3H]mazindol or [3H]cocaine in mice.
Bonnet, JJ; Costentin, J; Thibaut, F; Vaugeois, JM, 1996
)
0.29

Dosage Studied

ExcerptRelevanceReference
"Biogenic amines in pons and striatum have been dosed in twenty-four months old Wistar male rats."( [Biochemical changes in 24-month-old Wistar rats].
Della Zuana, O; Duhault, J; Lonchampt, M; Roman, F; Saint Romas, G, 1984
)
0.27
" 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
" AMPH at a dosage of 1 mg/kg significantly increased PEA concentration only in the striatum."( Effects of the administration of amphetamine, either alone or in combination with reserpine or cocaine, on regional brain beta-phenylethylamine and dopamine release.
Karoum, F; Mosnaim, AD; Wolf, ME,
)
0.13
" Behavioral deficits at the end of the 14-day dosing regime and on day 28 (i."( Intranasal administration of alpha-synuclein aggregates: a Parkinson's disease model with behavioral and neurochemical correlates.
Davydova, TV; Fomina, VG; Gruden, MA; Kudrin, VS; Morozova-Roche, LA; Narkevich, VB; Sewell, RD; Wang, C, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
human blood serum metaboliteAny metabolite (endogenous or exogenous) found in human blood serum samples.
human urinary metaboliteAny metabolite (endogenous or exogenous) found in human urine samples.
biomarkerA substance used as an indicator of a biological state.
[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 (4)

ClassDescription
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
primary amino compoundA compound formally derived from ammonia by replacing one hydrogen atom by an organyl group.
monomethoxybenzeneCompounds containing a benzene skeleton substituted with one methoxy group.
phenylethylamine
[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 (18)

PathwayProteinsCompounds
Neuronal System16650
Transmission across Chemical Synapses12250
Neurotransmitter clearance725
Clearance of dopamine413
Enzymatic degradation of dopamine by COMT310
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
Tyrosine metabolism ( Tyrosine metabolism )2841
22q11.2 copy number variation syndrome228
Renz2020 - GEM of Human alveolar macrophage with SARS-CoV-20490
Dopamine metabolism032
Neurotransmitter disorders819

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thyroid stimulating hormone receptorHomo sapiens (human)Potency0.12590.001318.074339.8107AID926
mitogen-activated protein kinase 1Homo sapiens (human)Potency39.81070.039816.784239.8107AID995
muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Potency0.03160.00106.000935.4813AID943
[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)
D(2) dopamine receptorRattus norvegicus (Norway rat)Kd150.40000.00030.81836.7000AID64790; AID64917; AID64919; AID64925
Trace amine-associated receptor 1Homo sapiens (human)EC50 (µMol)0.30800.01501.41437.1900AID1813802
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayTrace amine-associated receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityTrace amine-associated receptor 1Homo sapiens (human)
trace-amine receptor activityTrace amine-associated receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneTrace amine-associated receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID64919In vitro affinity at mutant D2 receptor (S197A) in C6 (glioma) cell membranes.2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
CoMFA-based prediction of agonist affinities at recombinant wild type versus serine to alanine point mutated D2 dopamine receptors.
AID64790In vitro affinity at mutant D2 receptor (S194A) in C6 (glioma) cell membranes.2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
CoMFA-based prediction of agonist affinities at recombinant wild type versus serine to alanine point mutated D2 dopamine receptors.
AID64917In vitro affinity at mutant D2 receptor (S194A) in C6 (glioma) cell membranes.2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
CoMFA-based prediction of agonist affinities at recombinant wild type versus serine to alanine point mutated D2 dopamine receptors.
AID1813802Agonist activity at recombinant human TAAR1 expressed in CHO-K1 cells assessed as increase in intracellular cAMP incubated for 30 mins by HTRF analysis2022ACS medicinal chemistry letters, Jan-13, Volume: 13, Issue:1
Ulotaront: A TAAR1 Agonist for the Treatment of Schizophrenia.
AID1813803Agonist activity at recombinant human TAAR1 expressed in CHO-K1 cells assessed as maximal increase in intracellular cAMP incubated for 30 mins by HTRF analysis relative to control2022ACS medicinal chemistry letters, Jan-13, Volume: 13, Issue:1
Ulotaront: A TAAR1 Agonist for the Treatment of Schizophrenia.
AID64925In vitro affinity at wild type Dopamine receptor D2 on C6 (glioma) cell membranes.2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
CoMFA-based prediction of agonist affinities at recombinant wild type versus serine to alanine point mutated D2 dopamine receptors.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (347)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990109 (31.41)18.7374
1990's97 (27.95)18.2507
2000's44 (12.68)29.6817
2010's65 (18.73)24.3611
2020's32 (9.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.58

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

MetricThis Compound (vs All)
Research Demand Index43.58 (24.57)
Research Supply Index5.91 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index67.15 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.58)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (0.82%)5.53%
Reviews6 (1.65%)6.00%
Case Studies6 (1.65%)4.05%
Observational2 (0.55%)0.25%
Other347 (95.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]