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N193

Sigma-Aldrich

1-Naphthylacetyl spermine trihydrochloride

Synonym(s):

NASPM trihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H34N4O · 3HCl
CAS Number:
1049731-36-3
Molecular Weight:
479.91
MDL number:
MFCD01321052
UNSPSC Code:
12352200
PubChem Substance ID:
24897539
NACRES:
NA.77

Assay

≥95% (HPLC)

Quality Level

100

form

powder

storage condition

desiccated
protect from light

color

white

solubility

H2O: ≥20 mg/mL

SMILES string

Cl.Cl.Cl.NCCCNCCCCNCCCNC(=O)Cc1cccc2ccccc12

InChI

1S/C22H34N4O.3ClH/c23-12-6-15-24-13-3-4-14-25-16-7-17-26-22(27)18-20-10-5-9-19-8-1-2-11-21(19)20;;;/h1-2,5,8-11,24-25H,3-4,6-7,12-18,23H2,(H,26,27);3*1H

InChI key

JNEOJAUJWOPWJS-UHFFFAOYSA-N

Application

1-Naphthylacetyl spermine trihydrochloride has been used for the inhibition of calcium-permeable AMPAR (α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor). It has also been used to study the involvement of AMPAR in biphasic activation of stress-activated protein kinase/extracellular signal-regulated kinase-1.

Biochem/physiol Actions

Blocks Ca2+ permeable AMPA receptor channels.

Other Notes

Synthetic analog of Joro spider toxin.

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000191114
0000163489
102M4620V
0000191114
0000163489

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A Takazawa et al.
Brain research, 706(1), 173-176 (1996-01-08)
The anticonvulsant effect of 1-naphthylacetyl spermine (1-NA-Spm), an analogue of Joro spider toxin, against amygdaloid kindled seizures was studied in rats. 1-NA-Spm (10, 20 and 40 micrograms/rat) dose-dependently improved kindled seizures and shortened the afterdischarge duration 30 min after the
H Tsubokawa et al.
Journal of neurophysiology, 74(1), 218-225 (1995-07-01)
1. We studied the effects of polyamine toxins derived from a spider venom on CA1 pyramidal neurons in gerbil hippocampal slices by patch-clamp recording. Joro spider toxin (JSTX) and its synthetic analogue, 1-naphthyl acetyl spermine (Naspm), which are known to
Blocking effect of 1-naphthyl acetyl spermine on Ca2+--p-ermeable AMPA receptors in cultured rat hippocampal neurons.
Koiki, M., et al.
Journal of Neuroscience Research, 29, 27-36 (1997)
Biphasic activation of apoptosis signal-regulating kinase 1-stress-activated protein kinase 1-c-Jun N-terminal protein kinase pathway is selectively mediated by Ca2+-permeable alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate receptors involving oxidative stress following brain ischemia in rat hippocampus
Zhang Q, et al
Neuroscience Letters, 337(1), 51-55 (2003)
beta-Adrenergic receptors regulate the acquisition and consolidation phases of aversive memory formation through distinct, temporally regulated signaling pathways
Schiff HC, et al.
Neuropsychopharmacology, 42(4), 895-895 (2017)
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