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Documenti fondamentali

A7127

Sigma-Aldrich

Agmatine sulfate salt

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

Sinonimo/i:

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

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About This Item

Formula condensata:
H2N(CH2)4NHC(=NH)NH2·H2SO4
Numero CAS:
Peso molecolare:
228.27
Beilstein:
3918807
Numero CE:
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.32

Nome del prodotto

Agmatine sulfate salt, ≥97%, powder

Livello qualitativo

Saggio

≥97%

Stato

powder

Colore

white to off-white

Punto di fusione

234-238 °C (lit.)

Solubilità

H2O: 50 mg/mL
ethanol: insoluble

Stringa SMILE

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)
PTAYFGHRDOMJGC-UHFFFAOYSA-N

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Applicazioni

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)

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


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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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