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Merck
CN

A0384

Arcaine sulfate salt

Synonym(s):

1,4-Diguanidinobutane sulfate salt

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About This Item

Empirical Formula (Hill Notation):
C6H16N6 · H2O4S
CAS Number:
14923-17-2
Molecular Weight:
270.31
NACRES:
NA.77
PubChem Substance ID:
24277954
UNSPSC Code:
12352200
MDL number:
MFCD00050545
Assay:
≥98% (TLC)
Form:
powder
Quality level:
200

Key Documents

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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)

SMILES string

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

InChI key

RWTGFMPOODRXIM-UHFFFAOYSA-N

biological source

synthetic (organic)

assay

≥98% (TLC)

form

powder

mp

>280 °C

solubility

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

Quality Level

200

Gene Information

human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907)

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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

Biochem/physiol Actions

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.

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
SLCL4063
SLCF8524
SLBT4233
SLBR2066V
SLBJ9045V

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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)
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
Wei-Ping Wang et al.
Brain research, 1084(1), 210-216 (2006-03-21)
Agmatine is a polyamine and has been considered as a novel neurotransmitter or neuromodulator in the central nervous system. In the present study, the neuroprotective effect of agmatine against cell damage caused by N-methyl-D-aspartate (NMDA) and glutamate was investigated in
Min-Ching Kuo et al.
The European journal of neuroscience, 27(7), 1731-1738 (2008-03-29)
Recent evidence indicates that the mature central visual system retains a higher degree of plasticity than traditionally assumed. However, little is known regarding the neuromodulatory factors that influence plasticity in the adult primary visual cortex (V1). We investigated the role
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