Page last updated: 2024-12-05

1-aminoanthraquinone

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

1-Aminoanthraquinone is a bright red crystalline solid that is an important intermediate in the synthesis of dyes, pigments, and other organic chemicals. It is synthesized by the nitration of anthraquinone followed by reduction of the nitro group to an amine. 1-Aminoanthraquinone exhibits a variety of biological activities, including antibacterial, antifungal, and antitumor effects. Its effects can be attributed to its ability to interact with DNA and other cellular components. The compound is also used as a fluorescent dye and a reagent in organic synthesis. Its study is driven by its potential applications in various fields, including the development of new pharmaceuticals, dyes, and materials.'

Cross-References

ID SourceID
PubMed CID6710
CHEMBL ID88502
SCHEMBL ID26348
MeSH IDM0140782

Synonyms (77)

Synonym
BIDD:GT0780
1-amino-anthraquinone
CHEMBL88502 ,
1-aminoquinone
nsc 30415
ai3-08918
alpha-aminoanthraquinone
einecs 201-423-5
brn 0396360
alpha-anthraquinonylamine
1-aminoanthrachinon [czech]
nsc 458
1-amino-9,10-anthracenedione
9,10-anthracenedione, 1-amino-
nsc-30415
nsc30415
1-aminoanthracene-9,10-dione
inchi=1/c14h9no2/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7h,15h
aminoanthraquinone
c.i. 37275
nsc-458
.alpha.-aminoanthraquinone
1-aminoanthraquinone
wln: l c666 bv ivj dz
diazo fast red al
9, 1-amino-
nsc458
1-amino-9,10-anthraquinone
1-aminoanthrachinon
anthraquinone, 1-amino-
82-45-1
.alpha.-anthraquinonylamine
1-aminoanthraquinone, 97%
STK076745
AC-11262
A0590
bdbm50094891
AKOS000119289
1-amino anthraquinone
BBL012347
9,10-anthracenedione, amino-
unii-u3xg95bni4
25620-59-1
u3xg95bni4 ,
unii-n5yyy1neui
n5yyy1neui ,
FT-0607339
1-aaq
SCHEMBL26348
1-aminoanthraquinone [mi]
aminoanthraquinone, 1-
azoic diazo no. 36
fast red al
DTXSID2052572
W-104175
smoke orange g
1-aminoanthra-9,10-quinone #
9,10-dioxo-9,10-dihydro-1-anthraceneamine
mfcd00001213
SR-01000027760-1
sr-01000027760
F21247
Z56779306
1-aminoanthraquinone 10 microg/ml in cyclohexane
1-aminoanthra-9,10-quinone
F0001-2104
AS-19059
1-amino-9,10-dihydroanthracene-9,10-dione
EN300-16786
AMY31060
Q27284591
A864406
1-amino anthraquinone; c.i. 37275; 1-amino-9,10-anthracenedione;1-aminoanthraquinone
?1-amino anthraquinone
CS-0010136
PD179451
SY049262
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A2aHomo sapiens (human)Ki3.20000.00001.06099.7920AID460874
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC50 (µMol)179.00000.00071.600310.0000AID144609; AID144610
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)179.00000.00071.630610.0000AID144609; AID144610
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)179.00000.00061.525710.0000AID144609; AID144610
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)179.00000.00071.747210.0000AID144609; AID144610
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC50 (µMol)179.00000.00071.741110.0000AID144609; AID144610
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC50 (µMol)179.00000.00071.741110.0000AID144609; AID144610
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC50 (µMol)179.00000.00071.741110.0000AID144609; AID144610
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (50)

Processvia Protein(s)Taxonomy
synaptic transmission, dopaminergicAdenosine receptor A2aHomo sapiens (human)
response to amphetamineAdenosine receptor A2aHomo sapiens (human)
regulation of DNA-templated transcriptionAdenosine receptor A2aHomo sapiens (human)
phagocytosisAdenosine receptor A2aHomo sapiens (human)
apoptotic processAdenosine receptor A2aHomo sapiens (human)
inflammatory responseAdenosine receptor A2aHomo sapiens (human)
cellular defense responseAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
cell-cell signalingAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, cholinergicAdenosine receptor A2aHomo sapiens (human)
central nervous system developmentAdenosine receptor A2aHomo sapiens (human)
blood coagulationAdenosine receptor A2aHomo sapiens (human)
sensory perceptionAdenosine receptor A2aHomo sapiens (human)
locomotory behaviorAdenosine receptor A2aHomo sapiens (human)
blood circulationAdenosine receptor A2aHomo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A2aHomo sapiens (human)
response to xenobiotic stimulusAdenosine receptor A2aHomo sapiens (human)
response to inorganic substanceAdenosine receptor A2aHomo sapiens (human)
positive regulation of glutamate secretionAdenosine receptor A2aHomo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmissionAdenosine receptor A2aHomo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A2aHomo sapiens (human)
response to purine-containing compoundAdenosine receptor A2aHomo sapiens (human)
response to caffeineAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
positive regulation of urine volumeAdenosine receptor A2aHomo sapiens (human)
vasodilationAdenosine receptor A2aHomo sapiens (human)
eating behaviorAdenosine receptor A2aHomo sapiens (human)
negative regulation of vascular permeabilityAdenosine receptor A2aHomo sapiens (human)
negative regulation of neuron apoptotic processAdenosine receptor A2aHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, sleepAdenosine receptor A2aHomo sapiens (human)
negative regulation of alpha-beta T cell activationAdenosine receptor A2aHomo sapiens (human)
astrocyte activationAdenosine receptor A2aHomo sapiens (human)
neuron projection morphogenesisAdenosine receptor A2aHomo sapiens (human)
positive regulation of protein secretionAdenosine receptor A2aHomo sapiens (human)
negative regulation of inflammatory responseAdenosine receptor A2aHomo sapiens (human)
regulation of mitochondrial membrane potentialAdenosine receptor A2aHomo sapiens (human)
membrane depolarizationAdenosine receptor A2aHomo sapiens (human)
regulation of calcium ion transportAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
inhibitory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
prepulse inhibitionAdenosine receptor A2aHomo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2aHomo sapiens (human)
positive regulation of long-term synaptic potentiationAdenosine receptor A2aHomo sapiens (human)
positive regulation of apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A2aHomo sapiens (human)
protein bindingAdenosine receptor A2aHomo sapiens (human)
calmodulin bindingAdenosine receptor A2aHomo sapiens (human)
lipid bindingAdenosine receptor A2aHomo sapiens (human)
enzyme bindingAdenosine receptor A2aHomo sapiens (human)
type 5 metabotropic glutamate receptor bindingAdenosine receptor A2aHomo sapiens (human)
identical protein bindingAdenosine receptor A2aHomo sapiens (human)
protein-containing complex bindingAdenosine receptor A2aHomo sapiens (human)
alpha-actinin bindingAdenosine receptor A2aHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A2aHomo sapiens (human)
intermediate filamentAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2aHomo sapiens (human)
membraneAdenosine receptor A2aHomo sapiens (human)
dendriteAdenosine receptor A2aHomo sapiens (human)
axolemmaAdenosine receptor A2aHomo sapiens (human)
asymmetric synapseAdenosine receptor A2aHomo sapiens (human)
presynaptic membraneAdenosine receptor A2aHomo sapiens (human)
neuronal cell bodyAdenosine receptor A2aHomo sapiens (human)
postsynaptic membraneAdenosine receptor A2aHomo sapiens (human)
presynaptic active zoneAdenosine receptor A2aHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2aHomo sapiens (human)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID398698Inhibition of lipid peroxidation in Sprague-Dawley rat heart mitochondria assessed as inhibition of FeSO4-induced oxygen consumption up to 0.3 mM relative to control1995Journal of natural products, Sep, Volume: 58, Issue:9
Effect of anthraquinone derivatives on lipid peroxidation in rat heart mitochondria: structure-activity relationship.
AID398699Inhibition of lipid peroxidation in Sprague-Dawley rat heart mitochondria assessed as inhibition of FeSO4-induced malondialdehyde formation up to 0.3 mM relative to control1995Journal of natural products, Sep, Volume: 58, Issue:9
Effect of anthraquinone derivatives on lipid peroxidation in rat heart mitochondria: structure-activity relationship.
AID460877Inhibition of human adenosine 2A receptor at 1 mM2010Journal of medicinal chemistry, Feb-25, Volume: 53, Issue:4
Structure-based discovery of novel chemotypes for adenosine A(2A) receptor antagonists.
AID144609Displacement of [3H]MK-801 from N-methyl-D-aspartate glutamate receptor2000Bioorganic & medicinal chemistry letters, Dec-04, Volume: 10, Issue:23
Aminoanthraquinones as novel ligands at the polyamine binding site on the N-methyl-D-aspartate receptor complex.
AID460874Inhibition of human adenosine 2A receptor2010Journal of medicinal chemistry, Feb-25, Volume: 53, Issue:4
Structure-based discovery of novel chemotypes for adenosine A(2A) receptor antagonists.
AID144610Displacement of [3H]-SPD from N-methyl-D-aspartate glutamate receptor2000Bioorganic & medicinal chemistry letters, Dec-04, Volume: 10, Issue:23
Aminoanthraquinones as novel ligands at the polyamine binding site on the N-methyl-D-aspartate receptor complex.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (6.25)18.7374
1990's2 (12.50)18.2507
2000's4 (25.00)29.6817
2010's5 (31.25)24.3611
2020's4 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 52.32

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 Index52.32 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.06 (4.65)
Search Engine Demand Index77.04 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (52.32)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]