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Sigma-Aldrich

Aminoguanidine bicarbonate

97%

Synonym(s):

Aminoguanidine hydrogencarbonate, Guanylhydrazine hydrogencarbonate

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About This Item

Linear Formula:
NH2NHC(=NH)NH2 · H2CO3
CAS Number:
2582-30-1
Molecular Weight:
136.11
Beilstein:
3569869
EC Number:
219-956-7
MDL number:
MFCD00012949
UNSPSC Code:
12352100
PubChem Substance ID:
24846902
NACRES:
NA.22

Assay

97%

mp

170-172 °C (dec.) (lit.)

solubility

H2O: soluble 2.7 g/L at 20 °C
H2O: soluble 3.3 g/L at 30 °C

SMILES string

OC(O)=O.NNC(N)=N

InChI

1S/CH6N4.CH2O3/c2-1(3)5-4;2-1(3)4/h4H2,(H4,2,3,5);(H2,2,3,4)

InChI key

OTXHZHQQWQTQMW-UHFFFAOYSA-N

Application

Aminoguanidine bicarbonate was used to study the effect of addition of polyamines to rat embryo cell cultures infected with adenovirus type 5.

Biochem/physiol Actions

Aminoguanidine bicarbonate protects the cells infected with adenovirus from chromosomal damage. Aminoguanidine is a specific and highly effective inhibitor of diamine oxidase present in fetal calf serum.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H317,H411

Precautionary Statements

P273 - P280 - P302 + P352

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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W A Gahl et al.
Chemico-biological interactions, 22(1), 91-98 (1978-07-01)
The inhibitory effect of the polyamines, spermidine and spermine, on the proliferation of human fibroblasts in culture was found to be reversed by the addition of aminoguanidine (AM), a specific and highly effective inhibitor of diamine oxidase (DAO) present in
Catiúcia R M O Matos et al.
Dalton transactions (Cambridge, England : 2003), 49(45), 16359-16367 (2020-05-28)
The Cu(ii) heptanuclear complex (Cu7atac) was synthesised using the hydrated amino acid ligand 2-(5-amino-1H-1,2,4-triazol-3-yl)acetic acid (Hatac·H2O). Single crystal X-ray diffraction analysis revealed a μ3-hydroxo bridged Cu(ii) heptanuclear complex, consisting of two triangular subunits and one Cu(ii) ion as a bridge
A J Bellett et al.
Chromosoma, 84(4), 571-583 (1982-01-01)
Adenovirus uncouples DNA replication from polyamine biosynthesis and causes chromosome aberrations in rodent cells. Addition of polyamines protected infected cells from this chromosome damage. Spermine was the only individual polyamine which protected. The diamine oxidase inhibitor aminoguanidine also protected. Neither
Sebastiano Intagliata et al.
Antioxidants (Basel, Switzerland), 10(1) (2020-12-31)
Resveratrol (RSV) is well known for its many beneficial activities, but its unfavorable physicochemical properties impair its effectiveness after systemic and topical administration; thus, several strategies have been investigated to improve RSV efficacy. With this aim, in this work, we
Paola Mirra et al.
Biochimica et biophysica acta, 1863(2), 440-449 (2016-11-20)
Methylglyoxal (MGO) is a reactive dicarbonyl produced as by-product of glycolysis, and its formation is heightened in hyperglycaemia. MGO plasma levels are two-fold to five-fold increased in diabetics and its accumulation promotes the progression of vascular complications. Impairment of endothelium-derived
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