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SML1856

Sigma-Aldrich

8-Aminoguanine

≥95% (HPLC)

Synonym(s):

2,8-Diamino-1,9-dihydro-6H-purin-6-one; 2,8-Diamino-hypoxanthine, NSC 23170

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About This Item

Empirical Formula (Hill Notation):
C5H6N6O
CAS Number:
28128-41-8
Molecular Weight:
166.14
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

0.1 M NaOH: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

O=C1C2=C(N=C(N)N2)NC(N)=N1

InChI

1S/C5H6N6O/c6-4-8-1-2(9-4)10-5(7)11-3(1)12/h(H6,6,7,8,9,10,11,12)

InChI key

WYDKPTZGVLTYPG-UHFFFAOYSA-N

Biochem/physiol Actions

8-Aminoguanine, a guanine derivative, is an orally available and highly efficacious potassium-sparing diuretic/natriuretic that increased sodium excretion by 17.2-fold and decrease potassium excretion by 71.0%. 8-Aminoguanine increases glucose excretion by 12.1-fold. Also, 8-Aminoguanine suppressed deoxycorticosterone/salt-induced hypertension.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Iwona Sieradzan et al.
The journal of physical chemistry. A, 118(35), 7194-7200 (2014-01-05)
Electronic structure methods are used to estimate differences in reaction barriers for transfer of an electron from singlet ππ* excited 8-aminoguanine (A) or deprotonated 8-aminoguanine anion (A(-)) to a proximal thymine dimer site compared to barriers when ππ* excited 8-oxoguanine
Edwin K Jackson et al.
Physiological reports, 2(5) (2014-05-30)
In cell culture, extracellular guanosine increases extracellular adenosine by attenuating the disposition of extracellular adenosine (American Journal of Physiology - Cell Physiology 304: C406-C421, 2013). The goal of this investigation was to determine whether this "guanosine-adenosine mechanism" is operative in
Edwin K Jackson et al.
The Journal of pharmacology and experimental therapeutics, 363(3), 358-366 (2017-09-21)
8-Aminoguanosine induces diuresis, natriuresis, glucosuria, and antikaliuresis. These effects could be mediated via 8-aminoguanosine's metabolism to 8-aminoguanine. In this study, we tested this hypothesis in anesthetized rats. First, we demonstrated that at 55- to 85-minutes post-i.v. administration, 8-aminoguanosine and 8-aminoguanine
Edwin K Jackson et al.
The Journal of pharmacology and experimental therapeutics, 359(3), 420-435 (2016-09-30)
In vivo, guanine moieties in DNA, RNA, guanine nucleotides, or guanosine or guanine per se can undergo nitration (for example, by peroxynitrite) or hydroxylation (for example, by superoxide anion) on position 8 of the purine ring. Subsequent catabolism of these

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