Aminoguanidine hydrochloride Chemical Properties

Melting point:

162-166 °C(lit.)

vapor pressure 

0Pa at 25℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Completely soluble in water

form 

Crystals

color 

White to off-white

Water Solubility 

506.7g/L at 20℃

Merck 

13,440

BRN 

3909606

InChI

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

InChIKey

UBDZFAGVPPMTIT-UHFFFAOYSA-N

SMILES

N(N)C(=N)N.[H]Cl

LogP

-3.55 at 20℃

CAS DataBase Reference

1937-19-5(CAS DataBase Reference)

EPA Substance Registry System

Hydrazinecarboximidamide, monohydrochloride (1937-19-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

ME8430000

F 

10-21

HS Code 

29280000

Aminoguanidine hydrochloride Usage And Synthesis

Description

Aminoguanidine is equipotent to L-NMMA and L-NNA as an inhibitor of iNOS. The IC₅₀ values for inhibition of mouse iNOS and rat nNOS are 5.4 and 160 μM, respectively. Aminoguanidine also inhibits induction of iNOS protein expression by endotoxin in rat macrophages. Aminoguanidine Hydrochloride is used in the synthetic preparation of highly selective and potent G-protein-coupled receptor kinase 2 (GRK2) inhibitor for potential treatment of heart failure.                                                            

Chemical Properties

white to off-white crystals

Uses

antitussive

Uses

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.

Uses

a-Glucosidase inhibitor; hydroxyethyl derivative of 1-deoxynojirimycin

Biological Functions

It is reported that aminoguanidine hydrochloride has two important biological effects. Firstly, it is effective for the prevention of formation of advanced glycation endproducts (AGEs) associated with pathogenesis of secondary complications to diabetes and with cardiovascular changes in aging. Aminoguanidine hydrochloride reacts rapidly with in vivo glycation α,β-dicarbonyl products such as methylglyoxal, glyoxal, and 3-deoxyglucosone to prevent the formation of AGEs.
Secondly, it inhibits of the individual isoforms of nitric oxide synthase (iNOS) which is one of three key enzymes generating nitric oxide (NO) from L-arginine. iNOS-derived nitric oxide plays an important role in numerous physiological (e.g. blood pressure regulation) and pathophysiological (e.g. inflammation) conditions.

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.

Flammability and Explosibility

Not classified

Biochem/physiol Actions

Inhibits both constitutive and inducible nitric oxide synthetase.

References

[1] JOLY G.A. Effects of NG-Methyl-L-arginine, NG-Nitro-L-arginine, and Aminoguanidine on Constitutive and Inducible Nitric Oxide Synthase in Rat Aorta[J]. Biochemical and biophysical research communications, 1994, 199 1: Pages 147-154. DOI: 10.1006/bbrc.1994.1207
[2] J A CORBETT  M L M. Selective inhibition of inducible nitric oxide synthase by aminoguanidine.[J]. Methods in enzymology, 1996, 268: 398-408. DOI: 10.1016/s0076-6879(96)68042-2
[3] H. RUETTEN  C. T. Prevention of the Expression of Inducible Nitric Oxide Synthase by Aminoguanidine or Aminoethyl-Isothiourea in Macrophages and in the Rat[J]. Biochemical and biophysical research communications, 1996, 225 2: Pages 525-530. DOI: 10.1006/bbrc.1996.1206

Aminoguanidine hydrochloride(1937-19-5)Related Product Information

• Copper(II) chloride
• Propionyl hydrazide
• Phthalimide
• Succinimide
• Octanoic hydrazide
• POLYETHERIMIDE
• 3,4,9,10-Perylenetetracarboxylic diimide
• EPINASTINE HYDROCHLORIDE
• AMINOGUANIDINE HYDROCHLORIDE