Page last updated: 2024-11-07

2,4,5-trihydroxyamphetamine

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

Description

2,4,5-trihydroxyamphetamine: structure given in first source; an in vitro metabolite of 2-hydroxy-4,5-(methylenedioxy)amphetamine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID126234
CHEMBL ID28225
SCHEMBL ID14478215
MeSH IDM0200097

Synonyms (23)

Synonym
brn 2416164
alpha-methyl-6-hydroxydopamine
pyrocatechol, 4-(2-aminopropyl)-5-hydroxy-, (+-)-
(rs)-6-hydroxy-alpha-methyldopamine
5-(2-aminopropyl)benzene-1,2,4-triol
5-(2-amino-propyl)-benzene-1,2,4-triol
5-(2-amino-propyl)-benzene-1,2,4-triol ((rs)-6-oh-alpha-meda)
bdbm50031342
41241-36-5
CHEMBL28225 ,
AKOS006275913
136706-33-7
1,2,4-benzenetriol, 5-(2-aminopropyl)-, (+-)-
2,4,5-trihydroxyamphetamine
tri-ho-a
unii-c6ji2489w2
c6ji2489w2 ,
SCHEMBL14478215
.alpha.-methyl-2,4,5-trihydroxyphenethylamine
1,2,4-benzenetriol, 5-(2-aminopropyl)-
.alpha.-methyl-6-hydroxydopamine
Q21099618
DTXSID90897244

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" LD50 studies in mice have established that 6-OH-alpha-Me-Dopa is over four times more toxic than alpha-Me-Dopa."( Synthetic and preliminary hemodynamic and whole animal toxicity studies on (R,S)-, (R)-, and (S)-2-methyl-3-(2,4,5-trihydroxyphenyl)alanine.
Castagnoli, N; Cheng, A; Karashima, D; Melmon, KL; Musson, DG; Rubiero, H, 1980
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium-dependent dopamine transporterRattus norvegicus (Norway rat)Ki0.01600.00030.37088.1600AID65474
TransporterRattus norvegicus (Norway rat)Ki0.02600.00010.866710.0000AID145874
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1131062Pressor activity in iv dosed normotensive Sprague-Dawley rat assessed as dose required for increasing systolic blood pressure to 30 mm Hg1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Synthesis, redox characteristics, and in vitro norepinephrine uptake inhibiting properties of 2-(2-mercapto-4,5-dihydroxyphenyl)ethylamine (6-mercaptodopamine).
AID139654Long term depletion of Dopamine(DA) in Whole mouse Brain at a low dose (60 nmol)1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
In vivo and in vitro studies on the neurotoxic potential of 6-hydroxydopamine analogs.
AID65474Evaluated for the Competitive inhibition of uptake of dopamine transporter1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
In vivo and in vitro studies on the neurotoxic potential of 6-hydroxydopamine analogs.
AID139816Long term depletion of Serotonin(5-HT) in Whole mouse Brain at a low dose (60 nmol)1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
In vivo and in vitro studies on the neurotoxic potential of 6-hydroxydopamine analogs.
AID139667Long term depletion of Norepinephrine (NE) in Whole mouse Brain at a low dose (60 nmol)1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
In vivo and in vitro studies on the neurotoxic potential of 6-hydroxydopamine analogs.
AID175697Evaluated for the stimulation of synaptosomal release of Dopamine (release constant)1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
In vivo and in vitro studies on the neurotoxic potential of 6-hydroxydopamine analogs.
AID175698Evaluated for the stimulation of synaptosomal release of norepinephrine (release constant)1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
In vivo and in vitro studies on the neurotoxic potential of 6-hydroxydopamine analogs.
AID145874Evaluated for the Competitive inhibition of uptake of norepinephrine1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
In vivo and in vitro studies on the neurotoxic potential of 6-hydroxydopamine analogs.
AID116921Compound was tested for toxicity (lethal dose) in male white swiss mice1980Journal of medicinal chemistry, Dec, Volume: 23, Issue:12
Synthetic and preliminary hemodynamic and whole animal toxicity studies on (R,S)-, (R)-, and (S)-2-methyl-3-(2,4,5-trihydroxyphenyl)alanine.
AID1135266Inhibition of norepinephrine release in sc dosed mouse heart administered 60 mins before [3H]-norepinephrine challenge1977Journal of medicinal chemistry, May, Volume: 20, Issue:5
N-(2,4,5-Trihydroxyphenehtyl)normetazocine, a potential irreversible inhibitor of the narcotic receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (50.00)18.7374
1990's3 (50.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.37

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

MetricThis Compound (vs All)
Research Demand Index12.37 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.37)

All Compounds (24.57)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]