Compounds > n(6)-methoxyadenosine
Page last updated: 2024-12-07

n(6)-methoxyadenosine

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

N(6)-methoxyadenosine (also known as 6-MeO-Ado) is an adenosine analog that acts as a potent agonist at the A2A adenosine receptor. It is often studied for its potential therapeutic effects, particularly in the treatment of neurodegenerative diseases and cancer. N(6)-methoxyadenosine has been shown to exhibit neuroprotective effects, potentially by reducing inflammation and oxidative stress. It has also been shown to inhibit tumor growth in preclinical studies. The compound is typically synthesized via methylation of adenosine using a strong base like sodium hydride and methyl iodide in a solvent like DMF. The resulting product can then be purified by recrystallization or chromatography.'

Cross-References

ID SourceID
PubMed CID101516
CHEMBL ID236766
SCHEMBL ID8713135
MeSH IDM0068282

Synonyms (11)

Synonym
adenosine, n-methoxy-
n6-methoxyadenosine
inosine, o-methyloxime
n4-methoxyadenosine
n-methoxyadenosine
19399-25-8
CHEMBL236766
(2r,3s,4r,5r)-2-(hydroxymethyl)-5-[6-(methoxyamino)purin-9-yl]oxolane-3,4-diol
nsc 529847
n(6)-methoxyadenosine
SCHEMBL8713135
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID300103Antimalarial activity against chloroquine,pyrimethamine-resistant Plasmodium falciparum K1 after 24 hrs2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300106Selectivity index, ratio of CC50 for human KB cells to IC50 for Plasmodium falciparum 3D72007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID595463Antiproliferative activity against human Caco2 cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
AID595462Antiproliferative activity against human HT-29 cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
AID521782Cytotoxicity against human HeLaS3 cells assessed cell viability at 2 mM after 24 hrs by Alamar blue assay2008Antimicrobial agents and chemotherapy, Mar, Volume: 52, Issue:3
Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.
AID300102Antimalarial activity against drug-sensitive Plasmodium falciparum 3D7 after 24 hrs2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300107Selectivity index, ratio of CC50 for human KB cells to IC50 for Plasmodium falciparum K12007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300104Antimalarial activity against chloroquine, pyrimethamine and cycloguanil-resistant Plasmodium falciparum VS1 after 24 hrs2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID595460Antiproliferative activity against human K562 cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
AID595461Antiproliferative activity against human MCF7 cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
AID300105Cytotoxicity against human KB cells2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID595459Antiproliferative activity against human HeLa cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
AID300108Selectivity index, ratio of CC50 for human KB cells to IC50 for Plasmodium falciparum VS12007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID521780Antiviral activity against Coxsackievirus infected in compound pre-treated HeLaS3 cells assessed as reduction in viral titer at 2 mM after 6 hrs relative to control2008Antimicrobial agents and chemotherapy, Mar, Volume: 52, Issue:3
Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.
AID521779Antiviral activity against Poliovirus infected in compound pre-treated HeLaS3 cells assessed as reduction in viral titer at 2 mM after 6 hrs relative to control2008Antimicrobial agents and chemotherapy, Mar, Volume: 52, Issue:3
Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.
[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-19901 (16.67)18.7374
1990's0 (0.00)18.2507
2000's2 (33.33)29.6817
2010's2 (33.33)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

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 Index12.56 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
hydroxylamine
amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.		1.9710hydroxylaminesalgal metabolite;
bacterial xenobiotic metabolite;
EC 1.1.3.13 (alcohol oxidase) inhibitor;
EC 4.2.1.22 (cystathionine beta-synthase) inhibitor;
EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor;
nitric oxide donor;
nucleophilic reagent
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.0310aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
pyrimethamine
Maloprim: contains above 2 cpds		2.0310aminopyrimidine;
monochlorobenzenes		antimalarial;
antiprotozoal drug;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor
cytidine
[no description available]		1.9710cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
podophyllotoxin
Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.		2.0310furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antimitotic;
antineoplastic agent;
keratolytic drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
6-hydroxyadenosine
[no description available]		2.7430
6-n-hydroxylaminopurine
N(6)-hydroxyadenine : A member of the class of 6-aminopurinnes that is adenine in which one of the exocyclic amino hydrogens is replaced by a hydroxy group.		2.03106-aminopurines;
hydroxylamines;
nucleobase analogue		mutagen;
teratogenic agent
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.7330adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
n(6)-methoxyadenine
[no description available]		2.0310
2-amino-n(6)-hydroxyadenine
2-amino-N(6)-hydroxyadenine: mutagen & bacterial growth inhibitor; structure in first source. 2-amino-6-hydroxyaminopurine : A 2,6-diaminopurine that is the N(6)-hydroxy derivative of 2,6-diamino-3H-purine.		2.03102,6-diaminopurines;
hydroxylamines;
nucleobase analogue		mutagen;
teratogenic agent
3'-c-methyladenosine
3'-C-methyladenosine: structure in first source		2.0610
1-aminoadenosine
1-aminoadenosine: structure		2.7430
ConditionIndicatedRelationship StrengthStudiesTrials
Diathesis
[description not available]		02.3110
2019 Novel Coronavirus Disease
[description not available]		02.3110