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A7127

Sigma-Aldrich

Agmatine sulfate salt

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

Synonym(s):

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

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About This Item

Linear Formula:
H2N(CH2)4NHC(=NH)NH2·H2SO4
CAS Number:
2482-00-0
Molecular Weight:
228.27
Beilstein:
3918807
EC Number:
219-617-3
MDL number:
MFCD00013109
UNSPSC Code:
12352200
PubChem Substance ID:
24277749
NACRES:
NA.32

product name

Agmatine sulfate salt, ≥97%, powder

Assay

≥97%

form

powder

color

white to off-white

mp

234-238 °C (lit.)

solubility

H2O: 50 mg/mL
ethanol: insoluble

SMILES string

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)

InChI key

PTAYFGHRDOMJGC-UHFFFAOYSA-N

Gene Information

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)

Biochem/physiol Actions

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.

Storage Class Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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