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Details

Stereochemistry ACHIRAL
Molecular Formula C5H5N5
Molecular Weight 135.1267
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-AMINOPURINE

SMILES

NC1=NC=C2NC=NC2=N1

InChI

InChIKey=MWBWWFOAEOYUST-UHFFFAOYSA-N
InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)

HIDE SMILES / InChI

Molecular Formula C5H5N5
Molecular Weight 135.1267
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

2-aminopurine is a purine analogue. It is known for its mutagenic effect by inducing DNA base-pair transitions. 2-aminopurine is widely used fluorescent probe of DNA structure and the perturbation of that structure by interaction with enzymes and other molecules. 2-aminopurine is a fluorescent nucleobase that provides the means to probe structure and dynamics of RNA molecules. 2-Aminopurine inhibits the double-stranded RNA-dependent protein kinase.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Valacyclovir and famciclovir therapy in herpes zoster.
2002-11
Sequence requirements in the catalytic core of the "10-23" DNA enzyme.
2002-10-25
Using 2-aminopurine fluorescence to measure incorporation of incorrect nucleotides by wild type and mutant bacteriophage T4 DNA polymerases.
2002-10-25
Understanding pain in herpes zoster: an essential for optimizing treatment.
2002-10-15
Progress in meeting today's demands in genital herpes: an overview of current management.
2002-10-15
Challenges in genital herpes simplex virus management.
2002-10-15
Cyclobutylpyrimidine dimer base flipping by DNA photolyase.
2002-10-11
Local conformational changes in the catalytic core of the trans-acting hepatitis delta virus ribozyme accompany catalysis.
2002-10-08
Treatment of recurrent hepatitis B infection in liver transplant recipients.
2002-10
Antiviral agents: Non-antiretroviral [correction of Nonantiviral] drugs.
2002-10
Fatal hepatitis B reactivation following discontinuation of nucleoside analogues for chronic hepatitis B.
2002-10
Use of 2-aminopurine and tryptophan fluorescence as probes in kinetic analyses of DNA polymerase beta.
2002-09-17
Fidelity of Escherichia coli DNA polymerase IV. Preferential generation of small deletion mutations by dNTP-stabilized misalignment.
2002-09-13
Role of DNA flexibility in sequence-dependent activity of uracil DNA glycosylase.
2002-09-10
Viral dynamics in chronic hepatitis B patients treated with lamivudine, lamivudine-famciclovir or lamivudine-ganciclovir.
2002-09
The use of antiviral monotherapy and combination therapy for patients with hepatitis B virus infection after liver transplantation.
2002-09
5-propynyluracil.diaminopurine: an efficient base-pair for non-enzymatic transcription of DNA.
2002-08-07
Anti-angiogenic activity of the purine analog 6-thioguanine.
2002-08
Nucleoside analogues for chronic hepatitis B: antiviral efficacy and viral resistance.
2002-07
Comparison of the efficacy of lamivudine and famciclovir in Asian patients with chronic hepatitis B: results of 24 weeks of therapy.
2002-07
Thymosin-alpha1 and famciclovir combination therapy activates T-cell response in patients with chronic hepatitis B virus infection in immune-tolerant phase.
2002-07
Antiviral agents in women's health: pharmacotherapeutics of treating influenza and herpes.
2002-06-20
Comparison of different treatment combinations for chronic hepatitis B infection.
2002-06
Successful antiviral treatment for fulminant reactivated hepatitis B after autologous stem cell transplantation and prophylaxis during subsequent allogeneic stem cell transplantation.
2002-06
Presteady-state analysis of a single catalytic turnover by Escherichia coli uracil-DNA glycosylase reveals a "pinch-pull-push" mechanism.
2002-05-31
In the fluorescent spotlight: global and local conformational changes of small catalytic RNAs.
2002-05-03
Adenoviral transfer of the melanoma differentiation-associated gene 7 (mda7) induces apoptosis of lung cancer cells via up-regulation of the double-stranded RNA-dependent protein kinase (PKR).
2002-04-15
Using 2-aminopurine fluorescence to detect base unstacking in the template strand during nucleotide incorporation by the bacteriophage T4 DNA polymerase.
2002-04-02
[Perspectives for the treatment and prevention of herpes simplex infections].
2002-04
[Genital herpes: epidemiology, transmission, clinic, asymptomatic viral excretion, impact on other sexually transmitted diseases, prevention, and treatment].
2002-04
Distinguishing "looped-out" and "stacked-in" DNA bulge conformation using fluorescent 2-aminopurine replacing a purine base.
2002-04
Temporal pattern of herpes simplex virus type 1 infection and cell death in the mouse brain stem: influence of guanosine nucleoside analogues.
2002-04
Reduction of postherpetic neuralgia in herpes zoster.
2002-03-22
Seroconversion after the addition of famciclovir therapy in a child with hepatitis B virus infection after liver transplantation who developed lamivudine resistance.
2002-03-15
Local disruption of DNA-base stacking by bulky base surrogates.
2002-03-07
Drugs for non-HIV viral infections.
2002-02-04
Lack of association between CYP2A5 induction and apoptosis in mouse primary hepatocytes.
2002-02-01
The epizootic haematopoietic necrosis virus (Iridoviridae) induces apoptosis in vitro.
2002-02
[Prevention and treatment of HBV reinfection following liver transplantation].
2002-02
How will we use the new antiviral agents for hepatitis B?
2002-02
Human interferon-gamma mRNA autoregulates its translation through a pseudoknot that activates the interferon-inducible protein kinase PKR.
2002-01-25
Herpes simplex virus infection.
2002-01
Lamivudine and famciclovir combination therapy with or without addition of interferon-alpha-2b for HBeAg-positive chronic hepatitis B: a pilot study.
2002
Genital herpes simplex virus infection in the adolescent: special considerations for management.
2002
Induction of premature mitosis in root meristem cells of Vicia faba and Pisum sativum by various agents is correlated with an increased level of protein phosphorylation.
2002
Conformation and dynamics of normal and damaged DNA.
2001-12
Antiepiligrin (laminin 5) cicatricial pemphigoid complicated and exacerbated by herpes simplex virus type 2 infection.
2001-11
Therapeutic advances in the management of hepatitis B and hepatitis C.
2001-10
Recent developments in herpesvirus therapy.
2001-03
[Treatment of genital herpes].
2001
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
5 mM 2-aminopurine enables wild-type p53-containing HCT116 cells to bypass adriamycin-induced G2/M arrest
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:26:50 GMT 2025
Edited
by admin
on Mon Mar 31 19:26:50 GMT 2025
Record UNII
O14B3U97FW
Record Status Validated (UNII)
Record Version
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Name Type Language
2-AMINOPURINE
Systematic Name English
NSC-24129
Preferred Name English
1H-PURIN-2-AMINE
Systematic Name English
PURINE, 2-AMINO-
Systematic Name English
SQ-22451
Code English
AMINOPURINE, 2-
Systematic Name English
9H-PURIN-2-AMINE
Systematic Name English
ISOADENINE
Common Name English
(9H-PURIN-2-YL)AMINE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID40196416
Created by admin on Mon Mar 31 19:26:50 GMT 2025 , Edited by admin on Mon Mar 31 19:26:50 GMT 2025
PRIMARY
PUBCHEM
9955
Created by admin on Mon Mar 31 19:26:50 GMT 2025 , Edited by admin on Mon Mar 31 19:26:50 GMT 2025
PRIMARY
MESH
D015075
Created by admin on Mon Mar 31 19:26:50 GMT 2025 , Edited by admin on Mon Mar 31 19:26:50 GMT 2025
PRIMARY
CAS
452-06-2
Created by admin on Mon Mar 31 19:26:50 GMT 2025 , Edited by admin on Mon Mar 31 19:26:50 GMT 2025
PRIMARY
NSC
24129
Created by admin on Mon Mar 31 19:26:50 GMT 2025 , Edited by admin on Mon Mar 31 19:26:50 GMT 2025
PRIMARY
CHEBI
479072
Created by admin on Mon Mar 31 19:26:50 GMT 2025 , Edited by admin on Mon Mar 31 19:26:50 GMT 2025
PRIMARY
FDA UNII
O14B3U97FW
Created by admin on Mon Mar 31 19:26:50 GMT 2025 , Edited by admin on Mon Mar 31 19:26:50 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-197-4
Created by admin on Mon Mar 31 19:26:50 GMT 2025 , Edited by admin on Mon Mar 31 19:26:50 GMT 2025
PRIMARY
WIKIPEDIA
2-AMINOPURINE
Created by admin on Mon Mar 31 19:26:50 GMT 2025 , Edited by admin on Mon Mar 31 19:26:50 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY