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A0384

Sigma-Aldrich

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
MDL number:
MFCD00050545
UNSPSC Code:
12352200
PubChem Substance ID:
24277954
NACRES:
NA.77

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

SMILES string

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)

InChI key

RWTGFMPOODRXIM-UHFFFAOYSA-N

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D L Yourick et al.
European journal of pharmacology, 371(2-3), 147-152 (1999-06-05)
The NMDA receptor complex is thought to be altered in kindling, an animal model for complex partial epilepsy. This receptor complex has several modulatory sites including those for glutamate, glycine and polyamines with activation resulting in altered cation channel opening.
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
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
Gustavo Petri Guerra et al.
Neurobiology of learning and memory, 96(2), 324-332 (2011-06-29)
Spermidine (SPD) is an endogenous polyamine that modulates N-methyl-D-aspartate (NMDA) receptor function, and has been reported to facilitate memory formation. In the current study we determined whether or not the PKA/CREB signaling pathway is involved in SPD-induced facilitation of memory
Ana Paula Chiapinotto Ceretta et al.
Psychopharmacology, 201(3), 405-411 (2008-09-02)
The polyamines putrescine, spermidine, and spermine are a group of aliphatic amines that may act as physiological modulators of the N-methyl-D-aspartate (NMDA) receptor, a glutamate receptor implicated in memory formation and consolidation. Arcaine is a competitive antagonist of the polyamine
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