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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)

Quality Level

200

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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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
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
Nandkishor Ramdas Kotagale et al.
Behavioural brain research, 213(2), 161-174 (2010-05-11)
Agmatine [2-(4-aminobutyl)guanidine] is an endogenous amine proposed as a neurotransmitter/neuromodulator that binds to multiple target receptors in brain. Besides, many central and peripheral functions, agmatine have been implicated in the process of drug addiction. The purpose of the present study
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
Anne Baron et al.
Neuropharmacology, 94, 19-35 (2015-01-24)
Development of the pharmacology of Acid-Sensing Ion Channels (ASICs) has become a key challenge to study their structure, their molecular and cellular functions and their physiopathological roles. This review provides a summary of the different compounds that directly interact with
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