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SML4086

Sigma-Aldrich

NitroSynapsin hydrochloride

new

≥98% (HPLC)

Synonym(s):

(1s,3r,5R,7S)-3-Amino-5,7-diethyladamantan-1-yl nitrate hydrochloride, 3-amino-5,7-diethyl-tricyclo[3.3.1.13,7]decan-1-ol 1-nitrate hydrochloride, NMI 6979 hydrochloride, NMT3 hydrochloride, NitroMemantine hydrochloride, YQW 036 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C14H24N2O3·HCl
CAS Number:
2445248-27-9
Molecular Weight:
304.81
UNSPSC Code:
12352200

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

N[C@]1(C2)C[C@@]3(CC)C[C@]2(O[N+]([O-])=O)C[C@](C1)(CC)C3.Cl

Biochem/physiol Actions

Extrasynaptic eNMDAR-selective blocker (over synaptic sNMDAR) with improved efficacy than memantine in cultures and in vivo; potent inhibitor of the SARS-CoV-2 virus entry.
NitroSynapsin is an NMDAR blocker that preferentially targets extrasynaptic over synaptic NMDA receptors (eNMDAR over sNMDAR) via a dual allosteric mechanism of open-channel blockage and NO/redox modulation. NitroSynapsin is significantly more effective than memantine (5 µM) in inhibiting the activation of rat cotical neurons due to NMDA release from co-cultured astrocytes upon stimulation by Aβ1-42 oligomers. When administered in the triple transgenic (3× tg) AD mouse model in vivo (216 mmol/kg bid. ip.), NitroSynapsin, but not memantine, significantly improves the location-novelty recognition. It is a potent inhibitor of the SARS-CoV-2 virus entry that prevents the virus spike protein binding to ACE2 (angiotensin-converting enzyme 2).

Caution

Hygroscopic

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315

Hazard Classifications

Acute Tox. 3 Oral - Skin Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Shu-Ichi Okamoto et al.
Neurobiology of disease, 127, 390-397 (2019-04-01)
Tuberous sclerosis (TSC) is an autosomal dominant disorder caused by heterozygous mutations in the TSC1 or TSC2 gene. TSC is often associated with neurological, cognitive, and behavioral deficits. TSC patients also express co-morbidity with anxiety and mood disorders. The mechanism
Chang-Ki Oh et al.
Nature chemical biology, 19(3), 275-283 (2022-09-30)
Prevention of infection and propagation of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is a high priority in the Coronavirus Disease 2019 (COVID-19) pandemic. Here we describe S-nitrosylation of multiple proteins involved in SARS-CoV-2 infection, including angiotensin-converting enzyme 2 (ACE2)
Maria Talantova et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(27), E2518-E2527 (2013-06-19)
Synaptic loss is the cardinal feature linking neuropathology to cognitive decline in Alzheimer's disease (AD). However, the mechanism of synaptic damage remains incompletely understood. Here, using FRET-based glutamate sensor imaging, we show that amyloid-β peptide (Aβ) engages α7 nicotinic acetylcholine

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