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HomeProduct name listAgmatine sulfate

Agmatine sulfate

Synonym(s):N-(4-Aminobutyl)guanidine sulfate salt;1-Amino-4-guanidinobutane sulfate salt;4-Guanidinobutylamine sulfate salt

  • CAS NO.:2482-00-0
  • Empirical Formula: C5H16N4O4S
  • Molecular Weight: 228.27
  • MDL number: MFCD00013109
  • EINECS: 219-617-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-07 21:39:59
Agmatine sulfate  Structural

What is Agmatine sulfate ?

Description

Agmatine sulfate is the sulfate of the Agmatine. Agmatine is an aninoguanidine that is naturally derived from the arginine. It can exert modulatory effect on many molecular targets such as neurotransmitter systems, opioid analgesia, ion channels, and nitric oxide (NO) synthesis and polyamine metabolism. It has been also found that it can reverse the pain induced from inflammation, neuropathy, and spinal cord injury. Those effects make it a potential candidate for multiple pharmacological applications in the future.

Chemical properties

White to off-white powder

The Uses of Agmatine sulfate

Agmatine Sulfate is a a polyamine derived from L-arginine (A769500) decarboxylation and is a known putative endogenous neurotransmitter at imidazoline receptors. Agmatine sulfate displaces clonidine a t α2-adrenergic and at imidazoline receptors and was recently shown to exert some neuroprotective effects.

The Uses of Agmatine sulfate

Agmatine is an intermediate in the biosynthesis of the polyamines putrescine and spermine. Agmatine binds with high affinity to α2-adrenergic receptors and imidazoline binding sites and produces blockade of the NMDA-receptor associated cation channels. Agmatine is a competitive inhibitor of nitric oxide synthase activity owing to mimicry of the natural NOS substrate arginine.

What are the applications of Application

Agmatine sulfate is an L-arginine decarboxy analog with neurotransmiter activity

Biological Activity

Arginine metabolite that is synthesized within bovine brain and exhibits clonidine-displacing substance (CDS) activity. Putative endogenous ligand for the imidazoline binding site.

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.

Purification Methods

Crystallise the salt from aqueous MeOH. The free base has m 101.5-103o, the gold chloride hydrochloride crystallises from H2O with m 223o(dec), and the picrate has m 236-238o. [Odo J Chem Soc Jpn 67 132 1946, Beilstein 4 I 420, 4 II 703, 4 III 575, 4 IV 1291.]

References

Fairbanks, C. A., et al. "Agmatine reverses pain induced by inflammation, neuropathy, and spinal cord injury." Proceedings of the National Academy of Sciences of the United States of America97.19(2000):10584.
Kolesnikov, Yuri, S. Jain, and G. W. Pasternak. "Modulation of opioid analgesia by agmatine." European Journal of Pharmacology296.1(1996):17-22.
Su, R. B., J. Li, and B. Y. Qin. "A biphasic opioid function modulator: agmatine. "Acta Pharmacologica Sinica24.7(2003):631.
Galea, Elena, et al. "Inhibition of mammalian nitric oxide synthases by agmatine, an endogenous polyamine formed by decarboxylation of arginine." Biochemical Journal 316 ( Pt 1).1(1996):247.
https://en.wikipedia.org/wiki/Agmatine

Properties of Agmatine sulfate

Melting point: 234-238 °C(lit.)
RTECS  ME8413000
storage temp.  Keep in dark place,Inert atmosphere,Room temperature
solubility  H2O: 50 mg/mL
form  powder
color  white to off-white
Water Solubility  Soluble in water, nearly insoluble in alcohol
Merck  14,188
BRN  3918807
InChI 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)
CAS DataBase Reference 2482-00-0(CAS DataBase Reference)

Safety information for Agmatine sulfate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Agmatine sulfate

InChIKey PTAYFGHRDOMJGC-UHFFFAOYSA-N
SMILES C(CCCN)NC(N)=N.S(O)(O)(=O)=O

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