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A7127

Agmatine sulfate salt

Name: Agmatine sulfate salt
Brand: SIGMA

≥97%, powder

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Synonym(s):

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

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

PubChem Substance ID:

24277749

NACRES:

NA.32

Quality Level

100

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

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Is agmatine a novel neurotransmitter in brain?

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

Evidence for oral agmatine sulfate safety--a 95-day high dosage pilot study with rats.

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

Linear biocompatible glyco-polyamidoamines as dual action mode virus infection inhibitors with potential as broad-spectrum microbicides for sexually transmitted diseases.

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

Agmatine: an endogenous clonidine-displacing substance in the brain.

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

Safety and Efficacy of Dietary Agmatine Sulfate in Lumbar Disc-associated Radiculopathy. An Open-label, Dose-escalating Study Followed by a Randomized, Double-blind, Placebo-controlled Trial.

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

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