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Merck
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Documentos clave

SML0790

Sigma-Aldrich

Iperoxo

≥98% (HPLC)

Sinónimos:

4-[(4,5-Dihydro-3-isoxazolyl)oxy]-N,N,N-trimethyl-2-butyn-1-aminium iodide

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About This Item

Fórmula empírica (notación de Hill):
C10H17IN2O2
Número de CAS:
247079-84-1
Peso molecular:
324.16
Código UNSPSC:
12352200
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to beige

solubilidad

H2O: 5 mg/mL, clear (warmed)

temp. de almacenamiento

2-8°C

InChI

1S/C9H14N2O2/c1-11(2)6-3-4-7-12-9-5-8-13-10-9/h5-8H2,1-2H3

Clave InChI

CADHNBBPGYVTOA-UHFFFAOYSA-N

Acciones bioquímicas o fisiológicas

Iperoxo forms an important building block for the class of G protein-coupled receptors modulators. Iperoxo specifically binds to the orthosteric site of the muscarinic acetylcholine receptor. It has a higher efficacy than the endogenous agonist acetylcholine.
Iperoxo is a muscarinic acetylcholine receptor superagonist. The pEC50 values for G-protein activation by acetylcholine and iperoxo in CHO cells expressing recombinant human M2 receptors are 7.6 and 10.1, respectively.

Características y beneficios

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Acetylcholine Receptors (Muscarinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H315,H319,H335

Clasificaciones de peligro

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
106M4616V
083M4602V

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Fabio Riefolo et al.
Journal of the American Chemical Society, 141(18), 7628-7636 (2019-04-24)
Light-triggered reversible modulation of physiological functions offers the promise of enabling on-demand spatiotemporally controlled therapeutic interventions. Optogenetics has been successfully implemented in the heart, but significant barriers to its use in the clinic remain, such as the need for genetic
Carlo Matera et al.
European journal of medicinal chemistry, 75, 222-232 (2014-02-19)
In this study, we synthesized and tested in vitro and in vivo two groups of bis(ammonio)alkane-type compounds, 6a-9a and 6b-9b, which incorporate the orthosteric muscarinic agonist iperoxo into a molecular fragment of the M2-selective allosteric modulators W84 and naphmethonium. The
R Schrage et al.
British journal of pharmacology, 169(2), 357-370 (2012-10-16)
Artificial agonists may have higher efficacy for receptor activation than the physiological agonist. Until now, such 'superagonism' has rarely been reported for GPCRs. Iperoxo is an extremely potent muscarinic receptor agonist. We hypothesized that iperoxo is a 'superagonist'. Signalling of
Jun Xu et al.
Molecular cell, 75(1), 53-65 (2019-05-20)
The M2 muscarinic acetylcholine receptor (M2R) is a prototypical GPCR that plays important roles in regulating heart rate and CNS functions. Crystal structures provide snapshots of the M2R in inactive and active states, but the allosteric link between the ligand

Artículos

Acetylcholine Receptors (Muscarinic)

Muscarinic acetylcholine receptors are G protein-coupled receptors (GPCRs) and mediate acetylcholine actions in the CNS and non-nervous tissues. Learn more about acetylcholine receptors and their role in cell signaling.

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