8-Azaadenine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 591121

CAS#: 1123-54-2

Description: 8-Azaadenine is a bioactive chemical.


Chemical Structure

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8-Azaadenine
CAS# 1123-54-2

Theoretical Analysis

MedKoo Cat#: 591121
Name: 8-Azaadenine
CAS#: 1123-54-2
Chemical Formula: C4H4N6
Exact Mass: 136.05
Molecular Weight: 136.120
Elemental Analysis: C, 35.30; H, 2.96; N, 61.74

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: 8-Azaadenine; NSC 32797; NSC32797; NSC-32797

IUPAC/Chemical Name: 7-Amino-1H-triazolo(4,5-d)pyrimidine

InChi Key: HRYKDUPGBWLLHO-UHFFFAOYSA-N

InChi Code: InChI=1S/C4H4N6/c5-3-2-4(7-1-6-3)9-10-8-2/h1H,(H3,5,6,7,8,9,10)

SMILES Code: NC1=C(NN=N2)C2=NC=N1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 136.12 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Minton JA, Rapp M, Stoffer AJ, Schultes NP, Mourad GS. Heterologous complementation studies reveal the solute transport profiles of a two-member nucleobase cation symporter 1 (NCS1) family in Physcomitrella patens. Plant Physiol Biochem. 2016 Mar;100:12-17. doi: 10.1016/j.plaphy.2015.12.014. Epub 2015 Dec 29. PubMed PMID: 26773540.

2: Stachelska-Wierzchowska A, Wierzchowski J, Bzowska A, Wielgus-Kutrowska B. Site-Selective Ribosylation of Fluorescent Nucleobase Analogs Using Purine-Nucleoside Phosphorylase as a Catalyst: Effects of Point Mutations. Molecules. 2015 Dec 28;21(1):E44. doi: 10.3390/molecules21010044. PubMed PMID: 26729076.

3: Chawla M, Credendino R, Oliva R, Cavallo L. Structural and Energetic Impact of Non-Natural 7-Deaza-8-Azaadenine and Its 7-Substituted Derivatives on H-Bonding Potential with Uracil in RNA Molecules. J Phys Chem B. 2015 Oct 15;119(41):12982-9. doi: 10.1021/acs.jpcb.5b06861. Epub 2015 Oct 1. PubMed PMID: 26389789.

4: Folkes LK, O'Neill P. DNA damage induced by nitric oxide during ionizing radiation is enhanced at replication. Nitric Oxide. 2013 Nov 1;34:47-55. doi: 10.1016/j.niox.2013.04.005. Epub 2013 Apr 26. PubMed PMID: 23623927.

5: Gobbo JP, Borin AC. On the mechanisms of triplet excited state population in 8-azaadenine. J Phys Chem B. 2012 Dec 6;116(48):14000-7. doi: 10.1021/jp3091599. Epub 2012 Nov 19. PubMed PMID: 23148644.

6: Jiang D, He Y, Budow S, Kazimierczuk Z, Eickmeier H, Reuter H, Seela F. 7-Amino-1-(2-deoxy-β-erythro-pentofuranosyl)-1H-1,2,3-triazolo[4,5-d]pyrimidine: an 8-azaadenine nucleoside with the nucleobase in a syn conformation. Acta Crystallogr C. 2010 Nov;66(Pt 11):o561-4. doi: 10.1107/S0108270110043088. Epub 2010 Oct 26. PubMed PMID: 21051825.

7: Afiuni-Zadeh S, Azimi G. A QSAR study for modeling of 8-azaadenine analogues proposed as A1 adenosine receptor antagonists using genetic algorithm coupling adaptive neuro-fuzzy inference system (ANFIS). Anal Sci. 2010;26(8):897-902. PubMed PMID: 20702945.

8: Sáenz L, Azpeitia A, Oropeza C, Jones LH, Fuchsova K, Spichal L, Strnad M. Endogenous cytokinins in Cocos nucifera L. in vitro cultures obtained from plumular explants. Plant Cell Rep. 2010 Nov;29(11):1227-34. doi: 10.1007/s00299-010-0906-9. Epub 2010 Aug 6. PubMed PMID: 20690021.

9: Kobayashi T, Kuramochi H, Harada Y, Suzuki T, Ichimura T. Intersystem crossing to excited triplet state of aza analogues of nucleic acid bases in acetonitrile. J Phys Chem A. 2009 Nov 5;113(44):12088-93. doi: 10.1021/jp905433s. PubMed PMID: 19795828.

10: Mansfield TA, Schultes NP, Mourad GS. AtAzg1 and AtAzg2 comprise a novel family of purine transporters in Arabidopsis. FEBS Lett. 2009 Jan 22;583(2):481-6. doi: 10.1016/j.febslet.2008.12.048. Epub 2008 Dec 31. PubMed PMID: 19121308.

11: Das SK, Masuda M, Hatashita M, Sakurai A, Sakakibara M. A new approach for improving cordycepin productivity in surface liquid culture of Cordyceps militaris using high-energy ion beam irradiation. Lett Appl Microbiol. 2008 Dec;47(6):534-8. doi: 10.1111/j.1472-765X.2008.02456.x. PubMed PMID: 19120921.

12: Gómez-Coca RB, Kapinos LE, Holý A, Vilaplana RA, González-Vílchez F, Sigel H. Ternary Copper(II) Complexes in Solution Formed With 8-Aza Derivatives of the Antiviral Nucleotide Analogue 9-[2-(Phosphonomethoxy)Ethyl]Adenine (PMEA). Met Based Drugs. 2000;7(6):313-24. doi: 10.1155/MBD.2000.313. PubMed PMID: 18475963; PubMed Central PMCID: PMC2365241.

13: Gómez-Coca RB, Holý A, Vilaplana RA, González-Vílchez F, Sigel H. Nickel(II), copper(II) and zinc(II) complexes of 9-[2- (phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA), the 8-aza derivative of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl] adenine (PMEA). Quantification of four isomeric species in aqueous solution. Bioinorg Chem Appl. 2004:331-52. doi: 10.1155/S1565363304000202. PubMed PMID: 18365084; PubMed Central PMCID: PMC2267076.

14: Giorgi I, Biagi G, Bianucci AM, Borghini A, Livi O, Leonardi M, Pietra D, Calderone V, Martelli A. N6-1,3-diphenylurea derivatives of 2-phenyl-9-benzyladenines and 8-azaadenines: synthesis and biological evaluation as allosteric modulators of A2A adenosine receptors. Eur J Med Chem. 2008 Aug;43(8):1639-47. Epub 2007 Oct 24. PubMed PMID: 18045744.

15: Massarelli I, Coi A, Pietra D, Nofal FA, Biagi G, Giorgi I, Leonardi M, Fiamingo F, Bianucci AM. QSAR study on a novel series of 8-azaadenine analogues proposed as A1 adenosine receptor antagonists. Eur J Med Chem. 2008 Jan;43(1):114-21. Epub 2007 Mar 1. PubMed PMID: 17418915.

16: Xi XL, Yang MM, Yang P. [The action mechanism of 8-azaadenine and its metal complexes with DNA]. Guang Pu Xue Yu Guang Pu Fen Xi. 2006 Dec;26(12):2272-5. Chinese. PubMed PMID: 17361728.

17: Xiong X, Ouyang J, Baeyens WR, Delanghe JR, Shen X, Yang Y. Enhanced separation of purine and pyrimidine bases using carboxylic multiwalled carbon nanotubes as additive in capillary zone electrophoresis. Electrophoresis. 2006 Aug;27(16):3243-53. PubMed PMID: 16858724.

18: Paluszynski JP, Klassen R, Rohe M, Meinhardt F. Various cytosine/adenine permease homologues are involved in the toxicity of 5-fluorocytosine in Saccharomyces cerevisiae. Yeast. 2006 Jul 15;23(9):707-15. PubMed PMID: 16845689.

19: Lin Y, Dion V, Wilson JH. A novel selectable system for detecting expansion of CAG.CTG repeats in mammalian cells. Mutat Res. 2005 May 2;572(1-2):123-31. PubMed PMID: 15790495.

20: Gómez-Coca RB, Kapinos LE, Holý A, Vilaplana RA, González-Vílchez F, Sigel H. Quantification of isomeric equilibria formed by metal ion complexes of 8-[2-(phosphonomethoxy)ethyl]-8-azaadenine (8,8aPMEA) and 9-[2-(phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA). Derivatives of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). J Biol Inorg Chem. 2004 Dec;9(8):961-72. Epub 2004 Oct 20. PubMed PMID: 15503234.