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Merck

A7127

Agmatine sulfate salt

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

Sinónimos:

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

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About This Item

Fórmula lineal:
H2N(CH2)4NHC(=NH)NH2·H2SO4
Número CAS:
2482-00-0
Peso molecular:
228.27
NACRES:
NA.32
PubChem Substance ID:
24277749
UNSPSC Code:
12352200
EC Number:
219-617-3
MDL number:
MFCD00013109
Beilstein/REAXYS Number:
3918807

Nombre del producto

Agmatine sulfate salt, ≥97%, powder

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)

SMILES string

OS(O)(=O)=O.NCCCCNC(N)=N

InChI key

PTAYFGHRDOMJGC-UHFFFAOYSA-N

assay

≥97%

form

powder

color

white to off-white

mp

234-238 °C (lit.)

solubility

H2O: 50 mg/mL
ethanol: insoluble

Quality Level

100

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.

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
MKCW1725
MKCV5573
MKCT7135
MKCR6591
MKCP5144

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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
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
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
Vegetables consumed in Brazilian cuisine as sources of bioactive amines
Dala P B M, et al.
Food Bioscience, 40, 100856-100856 (2021)
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
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