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Merck

N193

1-Naphthylacetyl spermine trihydrochloride

≥95% (HPLC), Ca2+ permeable AMPA receptor channel blocker, powder

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
UNSPSC Code:
12352200
PubChem Substance ID:
24897539
NACRES:
NA.77
MDL number:
MFCD01321052
Assay:
≥95% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated, protect from light

Key Documents

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Product Name

1-Naphthylacetyl spermine trihydrochloride,

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

assay

≥95% (HPLC)

form

powder

storage condition

desiccated, protect from light

color

white

solubility

H2O: ≥20 mg/mL

Quality Level

100

Related Categories

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

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
0000296325
0000191114
0000163489
102M4620V
0000191114

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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
Drosophila motor neuron boutons remodel through membrane blebbing coupled with muscle contraction.
Fernandes, et al.
Nature Communications, 14, 3352-3352 (2023)
Cornelia Strobel et al.
The Journal of physiology, 595(16), 5653-5669 (2017-06-09)
Dendritic and spine calcium imaging in combination with electrophysiology in acute slices revealed that in medial intercalated cells of the amygdala: Action potentials back-propagate into the dendritic tree, but due to the presence of voltage-dependent potassium channels, probably Kv4.2 channels
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)
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