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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Gad M Gilad et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 62, 758-762 (2013-10-22)
Agmatine, decarboxylated arginine, exerts beneficial effects in various experimental disease models. Clinical trials indicate the safety and effectiveness of short-term (up to 21 days) high dose regimens of oral agmatine sulfate, but longer term studies are lacking. This pilot study
D J Reis et al.
Trends in pharmacological sciences, 21(5), 187-193 (2000-04-29)
Recent evidence suggests that agmatine, which is an intermediate in polyamine biosynthesis, might be an important neurotransmitter in mammals. Agmatine is synthesized in the brain, stored in synaptic vesicles in regionally selective neurons, accumulated by uptake, released by depolarization, and
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