A7127
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:
Molecular Weight:
228.27
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
219-617-3
MDL number:
Beilstein/REAXYS Number:
3918807
Product Name
Agmatine sulfate salt, ≥97%, powder
Quality Level
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)
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| A7127-1G | 04061833383575 |
| A7127-5G | 04061833383582 |