A7127

Sigma-Aldrich

Agmatine sulfate salt

≥97%, powder

Synonym(s):
4-Guanidinobutylamine sulfate salt, 1-Amino-4-guanidinobutane sulfate salt, N-(4-Aminobutyl)guanidine sulfate salt
Linear Formula:
H2N(CH2)4NHC(=NH)NH2·H2SO4
CAS Number:
Molecular Weight:
228.27
Beilstein/REAXYS Number:
3918807
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32
Pricing and availability is not currently available.

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)

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Packaging

1, 5 g in glass bottle

Biochem/physiol Actions

Putative endogenous neurotransmitter at imidazoline receptors; displaces clonidine at α2-adrenergic and at imidazoline receptors; blocks NMDA-activated ion channels in hippocampal neurons.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
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...
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...
Zhenyi Han et al.
Transplantation, 104(9), 1906-1916 (2020-02-08)
Liver ischemia reperfusion injury (LIRI) is a common problem during surgical procedures of the liver. It causes severe inflammatory responses and cell death, eventually leading to serious liver damage. Agmatine (AGM) is an endogenous polyamine with analgesic, anti-inflammatory, and antiapoptotic...

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