Page last updated: 2024-12-05

dimethoxyphenylethylamine

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Description

Dimethoxyphenylethylamine: A derivative of phenethylamine containing two substituent methoxy groups in the phenyl ring. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3,4-dimethoxyphenylethylamine : An aromatic ether that is the derivative of 2-phenylethylamine with methoxy substituents at the 3- and 4-positions. It is an alkaloid isolated from the Cactaceae family. [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]

FloraRankFlora DefinitionFamilyFamily Definition
CactaceaefamilyThe cactus plant family of the order Caryophyllales, subclass Caryophyllidae, class Magnoliopsida. Cacti are succulent perennial plants well adapted to dry regions.[MeSH]CactaceaeThe cactus plant family of the order Caryophyllales, subclass Caryophyllidae, class Magnoliopsida. Cacti are succulent perennial plants well adapted to dry regions.[MeSH]

Cross-References

ID SourceID
PubMed CID8421
CHEMBL ID26019
CHEBI ID136995
SCHEMBL ID210639
SCHEMBL ID7319619
MeSH IDM0006453

Synonyms (121)

Synonym
MLS000515889
smr000112358
HMS3394A09
dopamine dimethyl ether
3,4-dimethoxy-.beta.-phenethylamine
3,4-dimethoxydopamine
dimethylmescaline
nsc6328
dimethoxyphenylethylamine
homoveratrylamine
dimethoxydopamine
nsc-6328
wln: z2r co1 do1
3,4-dimethoxyphenethylamine
dimpea
phenethylamine,4-dimethoxy-
120-20-7
2-(3,4-dimethoxyphenyl)ethylamine
3,4-dimethoxyphenylethylamine
benzeneethanamine,4-dimethoxy-
3,4-dimethoxy-.beta.-phenylethylamine
dmpea
.beta.-(3,4-dimethoxyphenyl)ethylamine
3,4-dimethoxyphenylethylamine(base)
3,4-dimethoxybenzeneethanamine
nsc26152
nsc-26152
inchi=1/c10h15no2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7h,5-6,11h2,1-2h
3,4-dimethoxyphenylethylamine (base)
brn 0474393
ai3-23876
einecs 204-376-9
nsc 16948
3,4-di-o-methyldopamine
3,4-dimethoxy-beta-phenylethylamine
beta-(3,4-dimethyoxyphenyl)ethylamine
o,o-dimethyldopamine
nsc-16948
nsc16948
phenethylamine, 3,4-dimethoxy-
benzeneethanamine, 3,4-dimethoxy-
OPREA1_397610
3,4-dimethoxyphenethylamine, 97%
NCIOPEN2_005995
2-(3,4-dimethoxyphenyl)ethanamine
STK397473
2-(3,4-dimethoxy-phenyl)-ethylamine
CHEBI:136995 ,
HMS2052A09
D0678
CHEMBL26019
AKOS000104026
3,4-dimethoxy-phenethylamine
NCGC00247022-01
3,4-dimethoxy phenylethylamine
3,4-dimethoxy phenethylamine
2-(3,4-dimethoxyphenyl)ethan-1-amine
b-3,4-dimethoxyphenylethylamine
b-(3,4-dimethoxyphenyl)ethyl amine
3,4-dimethyloxyphenylethylamine
beta-(3,4-dimethoxyphenyl)-ethylamine
b-(3,4-dimethoxyphenyl)ethylamine
2-(3,4-dimethoxyphenyl)-ethylamine
MLS001424180
HMS2269O22
CCG-101095
iqf9t435op ,
unii-iqf9t435op
4-13-00-02604 (beilstein handbook reference)
ec 204-376-9
FT-0608529
AM20060494
EPITOPE ID:119694
BBL023006
SCHEMBL210639
NC00345
SCHEMBL7319619
dopamine impurity c
dopamine hydrochloride impurity c [ep impurity]
homoveratryl amine
3,4-dimethyoxyphenylethylamine
2-(3,4-dimethoxy-phenyl)ethylamine
beta-(3,4-dimethoxyphenyl)ethylamine
2(3,4-dimethoxyphenyl)ethylamine
3,4-dimethoxy-beta-phenyl-ethylamine
3,4-di-methoxy-phenethylamine
2-(3',4'-dimethoxyphenyl)-ethylamine
2-(3,4-dimethoxyphenyl) ethylamine
2-(3,4-dimethoxy-phenyl)ethyl amine
[2-(3,4-dimethoxyphenyl)ethyl]amine
3,4-dimethoxy-phenylethylamine
beta-(3,4 -dimethoxyphenyl) ethylamine
DTXSID8059506
dopamine impurity c (3,4-dimethoxyphenethylamine)
3,4-dimethoxypheneethylamine
phenethyl amine, 3,4-dimethoxy
benzenethanamine, 3,4-dimethoxy-
2-(3,4-dimethoxyphenyl)ethanamine #
W-108484
mfcd00008188
F2190-0398
AC-8488
3,4-dimethoxy-benzeneethanamine
3, 4-dimethoxybenzeneethanamine
3, 4-dimethoxyphenethylamine
3,4-dimethoxy-benzenethanamine
2-(3,4-dimethoxyphenyl)ethanamine (acd/name 4.0)
3, 4-dimethoxy-beta-phenylethylamine
2-(3,4-dimethoxyphenyl)ethylamine (acd/name 4.0)
3, 4-dimethoxy-beta-phenethylamine
3,4-dimethoxy-beta-phenethylamine
3, 4-dimethoxyphenylethylamine(base)
homoveratrilamine
3,4-dimethoxyphenethylamine, pract.
CS-W023192
Q4634069
3,4-dimethoxyphenethyl amine
FS-4041
HY-Y0935
EN300-20212
Z104477298

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Papaverine and MPP+ were most toxic to TH-positive neurons among the compounds tested."( Neurotoxic effects of papaverine, tetrahydropapaverine and dimethoxyphenylethylamine on dopaminergic neurons in ventral mesencephalic-striatal co-culture.
Goto, K; Hattori, T; Mizuno, Y; Mochizuki, H; Nakamura, N, 1997
)
0.54
" 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
" This report describes a series of 10 patients who suffered adverse effects from 25B-NBOMe."( Case series: toxicity from 25B-NBOMe--a cluster of N-bomb cases.
Barrington, S; Gee, P; Jensen, BP; Moore, G; Schep, LJ, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" Pretreatment with either prazosin (5 x 10(-9) - 10(-8) M) or ketanserin (5 x 10(-9) - 10(-8) M) leads to decreased slopes and Emax in the 2C-B dose-response curves."( The action of the psychoactive drug 2C-B on isolated rat thoracic aorta.
Borges, Y; Cassels, BK; Gonzalez, E; Lobos, M, 1992
)
0.28
" The hydrochloride form showed incompatibility with the excipients used for oral dosage forms."( Preliminary preformulation studies of a 2-(3,4-dimethoxyphenyl)ethylamine derivative for oral administration at an exploratory stage of new drug development.
Hosokami, T; Kinuno, K; Konno, T; Mafune, E; Morita, M; Takasugi, N, 1995
)
0.29
"Primary outcome measures were (i) the percentage of samples purchased on-line and (ii) the chemical purity of powders (or dosage per tablet); adulteration; and the price per gram, blotter or tablet of drugs bought on-line compared with drugs bought off-line."( Purity, adulteration and price of drugs bought on-line versus off-line in the Netherlands.
Brunt, TM; van der Gouwe, D; van der Pol, P; van Laar, M, 2017
)
0.46
" The active dosage is very low, supposed to be less than 100 µg."( Retrospective Demonstration of 25I-NBOMe Acute Poisoning Using Hair Analysis.
Ameline, A; Farrugia, A; Kintz, P; Raul, JS, 2017
)
0.46
" In particular, little is known about the incorporation into the keratin matrix after intake and the correlation between dosage frequency of use, and hair concentrations."( Retrospective Demonstration of 25I-NBOMe Acute Poisoning Using Hair Analysis.
Ameline, A; Farrugia, A; Kintz, P; Raul, JS, 2017
)
0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
allergenA chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
[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 (3)

ClassDescription
phenylethylamine
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
[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 (20)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency8.91250.003245.467312,589.2998AID2517
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
Chain A, Ferritin light chainEquus caballus (horse)Potency11.22025.623417.292931.6228AID485281
P53Homo sapiens (human)Potency50.11870.07319.685831.6228AID504706
serine-protein kinase ATM isoform aHomo sapiens (human)Potency12.58930.707925.111941.2351AID485349
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency3.16230.251215.843239.8107AID504327
[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)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Kd4.36520.00042.58328.5114AID6406
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd4.36520.00012.62198.5114AID6406
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd4.36520.00012.29338.5114AID6406
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd4.36520.02342.74218.5114AID6406
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd4.36520.02342.74218.5114AID6406
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd4.36520.02342.74218.5114AID6406
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd4.36520.00042.47358.5114AID6406
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd4.36520.02342.74218.5114AID6406
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd4.36520.00012.70068.5114AID6406
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd4.36520.02342.74218.5114AID6406
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd4.36520.02342.74218.5114AID6406
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd4.36520.00082.62148.5114AID6406
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd4.36520.02342.74218.5114AID6406
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd4.36520.00082.62148.5114AID6406
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
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.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
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.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID273097Activity of human SSAO measured as hydrogen peroxide production at 1 mM relative to benzylamine oxidation2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking.
AID743654Antibacterial activity against Escherichia coli MG1655 overexpressing lolA assessed as growth inhibition after 16 hrs2013Bioorganic & medicinal chemistry letters, Apr-15, Volume: 23, Issue:8
Degradation of MAC13243 and studies of the interaction of resulting thiourea compounds with the lipoprotein targeting chaperone LolA.
AID743653Antibacterial activity against Bacillus subtilis 168 assessed as growth inhibition after 16 hrs2013Bioorganic & medicinal chemistry letters, Apr-15, Volume: 23, Issue:8
Degradation of MAC13243 and studies of the interaction of resulting thiourea compounds with the lipoprotein targeting chaperone LolA.
AID6406Affinity against 5-hydroxytryptamine receptors in rat fundus model1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Serotonin receptor affinities of psychoactive phenalkylamine analogues.
AID88883Hallucinogenic activity i.e; ratio of effective dose of mescaline to the effective dose in human1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
AID273098Activity of mouse SSAO measured as hydrogen peroxide production at 100 uM relative to benzylamine oxidation2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking.
AID89086Compound was tested for the psychotropic effect in human (activity is expressed in mescaline unit)1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline.
AID125220In vitro bovine plasma monoamine oxidase deamination with semicarbazide1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline.
AID1131957Hallucinogenic activity in human relative to mescaline1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Structure-activity studies on hallucinogenic amphetamines using molecular connectivity.
AID743652Antibacterial activity against Pseudomonas aeruginosa PAO1 assessed as growth inhibition after 16 hrs2013Bioorganic & medicinal chemistry letters, Apr-15, Volume: 23, Issue:8
Degradation of MAC13243 and studies of the interaction of resulting thiourea compounds with the lipoprotein targeting chaperone LolA.
AID125221In vitro bovine plasma monoamine oxidase deamination without semicarbazide1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline.
AID19263Log value of hallucinogenic activity was determined1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (143)

TimeframeStudies, This Drug (%)All Drugs %
pre-199051 (35.66)18.7374
1990's7 (4.90)18.2507
2000's10 (6.99)29.6817
2010's63 (44.06)24.3611
2020's12 (8.39)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.51

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 Index32.51 (24.57)
Research Supply Index5.07 (2.92)
Research Growth Index5.16 (4.65)
Search Engine Demand Index44.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.64%)5.53%
Reviews12 (7.64%)6.00%
Case Studies29 (18.47%)4.05%
Observational1 (0.64%)0.25%
Other114 (72.61%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]