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A7127

Sigma-Aldrich

Agmatine sulfate salt

≥97% (TLC), powder, ion channel blocker

Synonyme(s) :

1-Amino-4-guanidinobutane sulfate salt, 4-Guanidinobutylamine sulfate salt, N-(4-Aminobutyl)guanidine sulfate salt

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About This Item

Formule linéaire :
H2N(CH2)4NHC(=NH)NH2·H2SO4
Numéro CAS:
2482-00-0
Poids moléculaire :
228.27
Numéro Beilstein :
3918807
Numéro CE :
219-617-3
Numéro MDL:
MFCD00013109
Code UNSPSC :
12352200
ID de substance PubChem :
24277749
Nomenclature NACRES :
NA.32

product name

Agmatine sulfate salt, ≥97%, powder

Pureté

≥97%

Forme

powder

Couleur

white to off-white

Pf

234-238 °C (lit.)

Solubilité

H2O: 50 mg/mL
ethanol: insoluble

Chaîne SMILES 

OS(O)(=O)=O.NCCCCNC(N)=N

InChI

1S/C5H14N4.H2O4S/c6-3-1-2-4-9-5(7)8;1-5(2,3)4/h1-4,6H2,(H4,7,8,9);(H2,1,2,3,4)

Clé InChI

PTAYFGHRDOMJGC-UHFFFAOYSA-N

Informations sur le gène

human ... ADRA2A(150) , ADRA2B(151) , ADRA2C(152) , GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRINA(2907)

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Application

Agmatine sulfate salt has been used:
  • to study its effects on nod-like receptor protein 3 (NLRP3) inflammasome activation and cytokine responses in sub-chronic restraint stress rat models
  • as an N-methyl-D-aspartate (NMDA) receptor blocker to study its therapeutic effects on autistic behaviors in the valproic acid-induced animal model of autism
  • as a standard to determine the bioactive amines in vegetables by high-performance liquid chromatography (HPLC)

Actions biochimiques/physiologiques

Agmatine is a decarboxylated arginine that is present ubiquitously in all living organisms. It is found in food sources such as plant source food and animal products. It exhibits cryoprotective effects against several body functions such as nephroprotection, neuroprotection, gastroprotection, and cardioprotection. Agmatine also exhibits therapeutic effects against neurotrauma, neuropathic pain, diabetes, neurodegenerative diseases, and psychiatric diseases. It is involved in blocking many ionic channels such as ATP-sensitive K+ channels and voltage-gated Ca2+ channels. Agmatine modulates nitric oxide production and inhibits matrix metalloproteases.
Putative endogenous neurotransmitter at imidazoline receptors; displaces clonidine at α2-adrenergic and at imidazoline receptors; blocks NMDA-activated ion channels in hippocampal neurons.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Ceren Sahin et al.
Basic & clinical pharmacology & toxicology, 119(4), 367-375 (2016-04-12)
The activation of Nod-like receptor protein 3 (NLRP3) has lately been implicated in stress and depression as an initiator mechanism required for the production of interleukin (IL)-1β and IL-18. Agmatine, an endogenous polyamine widely distributed in mammalian brain, is a
Vegetables consumed in Brazilian cuisine as sources of bioactive amines
Dala P B M, et al.
Food Bioscience, 40, 100856-100856 (2021)
X C Yang et al.
The Journal of pharmacology and experimental therapeutics, 288(2), 544-549 (1999-01-26)
We investigated in rat hippocampus neurons whether 4-(aminobutyl)guanidine (agmatine), formed by decarboxylation of L-arginine by arginine decarboxylase and metabolized to urea and putrescine, can modulate the function of N-methyl-D-aspartate (NMDA) receptor channels. In cultured hippocampal neurons studied by whole-cell patch
Nicolò Mauro et al.
Scientific reports, 6, 33393-33393 (2016-09-20)
The initial steps of viral infections are mediated by interactions between viral proteins and cellular receptors. Blocking the latter with high-affinity ligands may inhibit infection. DC-SIGN, a C-type lectin receptor expressed by immature dendritic cells and macrophages, mediates human immunodeficiency
G Li et al.
Science (New York, N.Y.), 263(5149), 966-969 (1994-02-18)
Clonidine, an antihypertensive drug, binds to alpha 2-adrenergic and imidazoline receptors. The endogenous ligand for imidazoline receptors may be a clonidine-displacing substance, a small molecule isolated from bovine brain. This clonidine-displacing substance was purified and determined by mass spectroscopy to
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