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396494

Sigma-Aldrich

Aminoguanidine hydrochloride

≥98%

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Synonym(s):
Guanylhydrazine hydrochloride
Linear Formula:
NH2NHC(=NH)NH2 · HCl
CAS Number:
1937-19-5
Molecular Weight:
110.55
Beilstein:
3909606
EC Number:
217-707-7
MDL number:
MFCD00039074
UNSPSC Code:
12352100
PubChem Substance ID:
24864672
NACRES:
NA.22

Quality Level

200

Assay

≥98%

form

solid

mp

162-166 °C (lit.)

SMILES string

Cl.NNC(N)=N

InChI

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

InChI key

UBDZFAGVPPMTIT-UHFFFAOYSA-N

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General description

Aminoguanidine hydrochloride has been reported in a study as inhibitor of animal nitric oxide (NO)-synthase. Crystal structure of aminoguanidine hydrochloride has been investigated by Fourier and least squares method. Its crystals were monoclinic and the guanidine part of the aminoguanidinium ion is planar.

Application

Aminoguanidine hydrochloride may be employed as nitric oxide synthase (NOS) inhibitor to investigate its effect on the reduction of alveolar bone loss in ligature induced periodontitis in rats. It may be used in the synthesis of 5-guanylhydrazone derivatives, having antibacterial activity against antibacterial activity against both Escherichia coli and Staphylococcus aureus.

Biochem/physiol Actions

Inhibits both constitutive and inducible nitric oxide synthetase.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1B

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)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  4. Is there another aminoguanidine product suitable for cell culture?

    Aminoguanidine hemisulfate salt, Product No. A7009, is water soluble, so it may be worth trying. But we do not offer an aminoguanidine product that has been cell culture tested by Sigma-Aldrich.

  5. What impurities might be present in Product 396494, Aminoguanidine hydrochloride?

    Malononitrile and urea might be present in minute amounts.

  6. At what temperature should Product 396494, Aminoguanidine hydrochloride, be stored?

    The material should be stored at room temperature.

  7. What solvent can Product 396494, Aminoguanidine hydrochloride, be dissolved in?

    This product is soluble in water at 50 mg/mL, yielding a clear, colorless to faint yellow solution. Heat may be required to get the material to dissolve at that concentration.

  8. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

A K Glyan'ko
Biochemistry. Biokhimiia, 78(5), 471-476 (2013-07-16)
The level of nitric oxide (NO) in roots of 2-day-old etiolated pea (Pisum sativum L.) seedlings was investigated by fluorescence microscopy using the fluorescent probe 4,5-diaminofluorescein diacetate. Segments representing transversal (cross) cuts of the roots having thickness of 100 to
A K Gadad et al.
European journal of medicinal chemistry, 35(9), 853-857 (2000-09-28)
6-Arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamides 3 on Vilsmeier-Haak reaction produced 5-formyl-6-arylimidazo[2,1-b]-1,3, 4-thiadiazole-2-[N-(dimethylaminomethino)]sulfonamides 4, while 3 on treatment with potassium thiocyanate in the presence of bromine in acetic acid produced 5-thiocyanato-2-sulfonamides 6. Interaction of 4 with aminoguanidine hydrochloride in ethanol produced the corresponding 5-guanylhydrazone derivatives
Manju Gurung et al.
Bioresource technology, 129, 108-117 (2012-12-15)
A new adsorption gel has been developed by immobilizing N-aminoguanidine (AG), a chelating ligand, on persimmon tannin extract through consecutive reactions. Adsorption behavior of the gel was investigated for the adsorptive separation and recovery of precious metal ions from varying
Ivaylo P Ivanov et al.
Molecular cell, 70(2), 254-264 (2018-04-21)
Translation initiation is typically restricted to AUG codons, and scanning eukaryotic ribosomes inefficiently recognize near-cognate codons. We show that queuing of scanning ribosomes behind a paused elongating ribosome promotes initiation at upstream weak start sites. Ribosomal profiling reveals polyamine-dependent pausing
Lina Nordquist et al.
Advances in experimental medicine and biology, 765, 185-193 (2012-08-11)
Sustained hyperglycemia is closely associated with increased risk to develop nephropathy. We have previously reported alterations in the intrarenal oxygen metabolism already after the early onset of diabetes. Furthermore, formation of advanced glycation end-products (AGE) is postulated as a major
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