Page last updated: 2024-12-05

3-aminopyridine

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

3-aminopyridine is an organic compound with the formula C5H6N2. It is a white solid that is soluble in water. 3-aminopyridine is a versatile building block in organic synthesis and is used as a precursor to various pharmaceuticals and other fine chemicals. It is also used in the preparation of herbicides, pesticides, and dyes. 3-aminopyridine is known to be a potent inhibitor of the enzyme monoamine oxidase (MAO). MAO is an enzyme that breaks down neurotransmitters such as dopamine, norepinephrine, and serotonin. Inhibition of MAO can lead to an increase in the levels of these neurotransmitters in the brain, which can have a variety of effects, including mood elevation, increased alertness, and improved cognitive function. 3-aminopyridine has also been shown to have anti-inflammatory and analgesic properties. 3-aminopyridine is a promising candidate for the development of new drugs for the treatment of a variety of conditions, including depression, anxiety, Parkinson's disease, and Alzheimer's disease. 3-aminopyridine is synthesized from the reaction of 3-bromopyridine with ammonia. It is often studied for its potential therapeutic properties, particularly in the context of neurological disorders and drug development.'

Cross-References

ID SourceID
PubMed CID10009
CHEMBL ID25541
MeSH IDM0098400

Synonyms (71)

Synonym
pyridin-3-yl-amine
AC-907/25014070
pyridin-3-ylamine
brn 0105692
beta-aminopyridine
ai3-52546
nsc 15040
einecs 207-322-2
wln: t6nj cz
amino-3 pyridine
3-pyridylamine
3-pyridinamine
nsc15040
3-aminopyridine ,
nsc-15040
pyridine, 3-amino-
462-08-8
.beta.-aminopyridine
pyridin-3-amine
inchi=1/c5h6n2/c6-5-2-1-3-7-4-5/h1-4h,6h
un2671
3-aminopyridine, 99%
3AP ,
A0413
m-aminopyridine
CHEMBL25541 ,
AKOS000119614
NCGC00249092-01
unii-69je8p2l84
m-aminopyridine [un2671] [poison]
69je8p2l84 ,
5-22-09-00003 (beilstein handbook reference)
cas-462-08-8
dtxsid9047461 ,
dtxcid7027461
tox21_303451
NCGC00257364-01
tox21_201650
NCGC00259199-01
A827009
STL163954
3-amino pyridine
FT-0687286
BP-12818
FT-0615067
AM20051207
CX1211
3-pyridinylamine
.beta.-aminopyridine [mi]
un-2671
pyridin-3-yl amine
3-aminopyridin
3-amino-pyridin
5-aminopyridine
pyridine-3-ylamine
3-pyridine amine
3-amino-pyridine
pyridine-3-amine
3-amino pyridin
3-aminopryidine
un 2671
PS-9358
mfcd00006400
F1995-0204
bdbm50122005
BCP22961
Q4634118
EN300-21243
3-aminopyridine-d6
1219805-61-4
Z104494800

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" That a lesion of the inferior olive almost completely prevents the neurotoxicity demonstrates that ibogaine is not directly toxic to Purkinje cells, but that the toxicity is indirect and dependent on integrity of the olivocerebellar projection."( The olivocerebellar projection mediates ibogaine-induced degeneration of Purkinje cells: a model of indirect, trans-synaptic excitotoxicity.
Molliver, ME; O'Hearn, E, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency55.48150.003041.611522,387.1992AID1159552
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency78.36970.001530.607315,848.9004AID1224841
estrogen nuclear receptor alphaHomo sapiens (human)Potency54.94770.000229.305416,493.5996AID743069
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency21.87510.023723.228263.5986AID743223
aryl hydrocarbon receptorHomo sapiens (human)Potency55.48150.000723.06741,258.9301AID743085
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency0.24780.000323.4451159.6830AID743065
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Botulinum neurotoxin type A Clostridium botulinumIC50 (µMol)3.30000.50003.16927.2000AID1434686
D-amino-acid oxidaseHomo sapiens (human)IC50 (µMol)10,000.00000.00401.119910.0000AID1247844
D-aspartate oxidaseHomo sapiens (human)IC50 (µMol)10,000.00000.00400.39370.8550AID1247843
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
proline catabolic processD-amino-acid oxidaseHomo sapiens (human)
digestionD-amino-acid oxidaseHomo sapiens (human)
D-amino acid catabolic processD-amino-acid oxidaseHomo sapiens (human)
D-serine catabolic processD-amino-acid oxidaseHomo sapiens (human)
dopamine biosynthetic processD-amino-acid oxidaseHomo sapiens (human)
D-alanine catabolic processD-amino-acid oxidaseHomo sapiens (human)
D-serine metabolic processD-amino-acid oxidaseHomo sapiens (human)
neutrophil-mediated killing of gram-negative bacteriumD-amino-acid oxidaseHomo sapiens (human)
inseminationD-aspartate oxidaseHomo sapiens (human)
grooming behaviorD-aspartate oxidaseHomo sapiens (human)
regulation of cell communicationD-aspartate oxidaseHomo sapiens (human)
D-amino acid catabolic processD-aspartate oxidaseHomo sapiens (human)
hormone metabolic processD-aspartate oxidaseHomo sapiens (human)
nervous system processD-aspartate oxidaseHomo sapiens (human)
aspartate catabolic processD-aspartate oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
protein transmembrane transporter activityBotulinum neurotoxin type A Clostridium botulinum
D-amino-acid oxidase activityD-amino-acid oxidaseHomo sapiens (human)
protein bindingD-amino-acid oxidaseHomo sapiens (human)
identical protein bindingD-amino-acid oxidaseHomo sapiens (human)
FAD bindingD-amino-acid oxidaseHomo sapiens (human)
protein bindingD-aspartate oxidaseHomo sapiens (human)
D-aspartate oxidase activityD-aspartate oxidaseHomo sapiens (human)
D-glutamate oxidase activityD-aspartate oxidaseHomo sapiens (human)
FAD bindingD-aspartate oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
mitochondrial outer membraneD-amino-acid oxidaseHomo sapiens (human)
extracellular regionD-amino-acid oxidaseHomo sapiens (human)
cytoplasmD-amino-acid oxidaseHomo sapiens (human)
peroxisomal matrixD-amino-acid oxidaseHomo sapiens (human)
cytosolD-amino-acid oxidaseHomo sapiens (human)
cell projectionD-amino-acid oxidaseHomo sapiens (human)
presynaptic active zoneD-amino-acid oxidaseHomo sapiens (human)
cytoplasmD-amino-acid oxidaseHomo sapiens (human)
peroxisomeD-aspartate oxidaseHomo sapiens (human)
peroxisomeD-aspartate oxidaseHomo sapiens (human)
peroxisomal matrixD-aspartate oxidaseHomo sapiens (human)
cytosolD-aspartate oxidaseHomo sapiens (human)
cytoplasmD-aspartate oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID30382Compound was evaluated for ability to enhance the binding of (+/-)-[3H]nicotine to the rat brain P2 fraction at binding site 1; 10e-10-10e-61985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Structure-activity relationships of some pyridine, piperidine, and pyrrolidine analogues for enhancing and inhibiting the binding of (+/-)-[3H]nicotine to the rat brain P2 preparation.
AID30389Ability to enhance the binding of (+/-)-[3H]nicotine to the rat brain P2 fraction at binding site 21985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Structure-activity relationships of some pyridine, piperidine, and pyrrolidine analogues for enhancing and inhibiting the binding of (+/-)-[3H]nicotine to the rat brain P2 preparation.
AID30391Ability to enhance the binding of (+/-)-[3H]nicotine to the rat brain P2 fraction at binding site 3.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Structure-activity relationships of some pyridine, piperidine, and pyrrolidine analogues for enhancing and inhibiting the binding of (+/-)-[3H]nicotine to the rat brain P2 preparation.
AID619514Selectivity index, ratio of CC50 for human CEM-T4 cells to EC50 for HIV1 infected human CEM-T4 cells2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity.
AID1247844Inhibition of human recombinant DAO expressed in Escherichia coli BL21(DE3) using D-Asp and D-Ala assessed as 2-oxo acid production after 10 mins by colorimetric assay2015Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18
Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1247843Inhibition of human recombinant DDO expressed in Escherichia coli BL21(DE3) using D-Asp and D-Ala assessed as 2-oxo acid production after 10 mins by colorimetric assay2015Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18
Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID30521Compounds was evaluate for their ability to enhance (+/-)-[3H]nicotine binding at a dose range 10 E -10 - 10 E -6 M was reported1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Structure-activity relationships of some pyridine, piperidine, and pyrrolidine analogues for enhancing and inhibiting the binding of (+/-)-[3H]nicotine to the rat brain P2 preparation.
AID619512Cytotoxicity against human CEM-T4 cells assessed as cell viability at 200 uM after 7 days by MTT assay2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity.
AID619513Antiviral activity against HIV1 infected in human CEM-T4 cells assessed as reduction in viral protein p24 production preincubated for 24 hrs measured after 8 days by MTT assay2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity.
AID619509Dissociation constant, pKa of the compound in aqueous solution2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity.
AID1434686Inhibition of protease activity of recombinant full length Clostridium botulinum Hall BoNT/A light chain using SNAP-25 peptide (187 to 203 residues) as substrate after 5 mins by HPLC analysis2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
A matrix-focused structure-activity and binding site flexibility study of quinolinol inhibitors of botulinum neurotoxin serotype A.
AID30378Maximum percent of inhibition of binding was determined1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Structure-activity relationships of some pyridine, piperidine, and pyrrolidine analogues for enhancing and inhibiting the binding of (+/-)-[3H]nicotine to the rat brain P2 preparation.
AID30377Maximum percent of enhancement of binding.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Structure-activity relationships of some pyridine, piperidine, and pyrrolidine analogues for enhancing and inhibiting the binding of (+/-)-[3H]nicotine to the rat brain P2 preparation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (44)

TimeframeStudies, This Drug (%)All Drugs %
pre-199018 (40.91)18.7374
1990's5 (11.36)18.2507
2000's9 (20.45)29.6817
2010's10 (22.73)24.3611
2020's2 (4.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.08

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 Index38.08 (24.57)
Research Supply Index3.85 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index52.19 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.08)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.17%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other45 (97.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]