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396494

Sigma-Aldrich

Aminoguanidine hydrochloride

≥98%

Synonym(s):

Guanylhydrazine hydrochloride

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About This Item

Linear Formula:
NH2NHC(=NH)NH2 · HCl
CAS Number:
Molecular Weight:
110.55
Beilstein:
3909606
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98%

form

solid

mp

162-166 °C (lit.)

functional group

amine
hydrazine

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1B

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

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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
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
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
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
Manuella Lanzetti et al.
Free radical biology & medicine, 53(11), 1993-2001 (2012-09-25)
Our aim was to investigate the role of oxidative stress in elastase-induced pulmonary emphysema. C57BL/6 mice were subjected to pancreatic porcine elastase (PPE) instillation (0.05 or 0.5 U per mouse, i.t.) to induce pulmonary emphysema. Lungs were collected on days

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