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A0384

Sigma-Aldrich

Arcaine sulfate salt

Synonyme(s) :

1,4-Diguanidinobutane sulfate salt

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About This Item

Formule empirique (notation de Hill):
C6H16N6 · H2O4S
Numéro CAS:
Poids moléculaire :
270.31
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Pureté

≥98% (TLC)

Forme

powder

Pf

>280 °C

Solubilité

1 M NaOH: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

Chaîne SMILES 

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

InChI

1S/C6H16N6.H2O4S/c7-5(8)11-3-1-2-4-12-6(9)10;1-5(2,3)4/h1-4H2,(H4,7,8,11)(H4,9,10,12);(H2,1,2,3,4)

Clé InChI

RWTGFMPOODRXIM-UHFFFAOYSA-N

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Application

Arcaine sulfate salt has been used as an N-methyl-d-aspartate (NMDA) receptor effector/antagonist:
  • to evaluate its effects on the acquisition of electrical kindling of the amygdala
  • to compare its effects with agmatine and MK801 on NMDA- or glutamate-induced neuronal damage
  • to study its effects on cell-free translation of synthetic polynucleotide

Actions biochimiques/physiologiques

Arcaine sulfate salt (1,4-diguanidinobutane), a polyamine, is an antagonist of the polyamine binding site of the N-methyl-d-aspartate (NMDA) receptor. Arcaine, an agmatine analog, along with ifenprodil, might have a possibility for therapeutic management in epileptic disorders.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

Nádia Aléssio Velloso Bellé et al.
Brain research, 1008(2), 245-251 (2004-05-18)
Polyamines, among other functions, are considered to act as a free radical scavenger and antioxidant. The quinolinic acid (QA), sodium nitroprusside (SNP) and iron (Fe+2) stimulate production of free radicals and lipid peroxidation. In the present study, we investigated the
Arcaine is a competitive antagonist of the polyamine site on the NMDA receptor.
I J Reynolds
European journal of pharmacology, 177(3), 215-216 (1990-02-27)
Raquele Kipper Mariani et al.
Psychopharmacology, 215(3), 483-491 (2011-03-02)
Arcaine is a competitive antagonist of the polyamine binding site at the N-methyl-D-aspartic acid receptor which induces state-dependent recall. However, no study has addressed the involvement of other neurotransmitter/neuromodulators in arcaine-induced state dependency. The current study investigates whether the opioid
R C Araneda et al.
Biophysical journal, 76(6), 2899-2911 (1999-06-04)
Polyamines such as spermine are thought to be endogenous regulators of NMDA (N-methyl-D-aspartate)-type glutamate receptors. Polyamine block of NMDA receptors was studied in excised outside-out patches from rat hippocampal neurons and Xenopus oocytes expressing recombinant receptors. Extracellular spermine and arcaine
J F Atkins et al.
The Journal of biological chemistry, 250(14), 5688-5695 (1975-07-25)
Addition of the polyamines spermidine, spermine, or putrescine to a fractionated mammalian cell-free protein-synthesis system programmed by a variety of mRNAs results in a 3- to 5-fold stimulation of amino acid incorporation over that found in the absence of added

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