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A7127

Sigma-Aldrich

Agmatine sulfate salt

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

Synonyma:

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

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About This Item

Lineární vzorec:
H2N(CH2)4NHC(=NH)NH2·H2SO4
Číslo CAS:
2482-00-0
Molekulová hmotnost:
228.27
Beilstein/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Osvědčení o analýze (COA)

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E-64 N-[N-(L-3-Trans-carboxirane-2-carbonyl)-L-leucyl]-agmatine

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Sigma-Aldrich

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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)
Ory Keynan et al.
Pain medicine (Malden, Mass.), 11(3), 356-368 (2010-05-08)
Objective. Agmatine, decarboxylated arginine, was shown in preclinical studies to exert efficacious neuroprotection by interacting with multiple molecular targets. This study was designed to ascertain safety and efficacy of dietary agmatine sulfate in herniated lumbar disc-associated radiculopathy. Study Design. First
Ji-Woon Kim et al.
Neuropharmacology, 113(Pt A), 71-81 (2016-11-05)
Autism spectrum disorder (ASD) is an immensely challenging developmental disorder characterized primarily by two core behavioral symptoms of social communication deficits and restricted/repetitive behaviors. Investigating the etiological process and identifying an appropriate therapeutic target remain as formidable challenges to overcome
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
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