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SML0790

Iperoxo

Name: Iperoxo
Brand: SIGMA

≥98% (HPLC), Acetylcholine receptor agonist, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₇IN₂O₂

CAS Number:

247079-84-1

Molecular Weight:

324.16

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Iperoxo, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H₂O: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

InChI

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

InChI key

CADHNBBPGYVTOA-UHFFFAOYSA-N

Related Categories

Bioactive Small Molecules

Biochem/physiol Actions

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.

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.

Features and Benefits

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.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000518224

0000487907

0000391166

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Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.

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

Optical Control of Cardiac Function with a Photoswitchable Muscarinic Agonist.

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

Agonists with supraphysiological efficacy at the muscarinic M2 ACh receptor.

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

Conformational Complexity and Dynamics in a Muscarinic Receptor Revealed by NMR Spectroscopy.

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

Articles

Muscarinic Acetylcholine Receptors

Muscarinic acetylcholine receptors mediate acetylcholine actions in CNS and non-nervous tissues, crucial for cell signaling.

DISCOVER Bioactive Small Molecules for Neuroscience

Global Trade Item Number

SKU	GTIN
SML0790-5MG	04061832076539
SML0790-25MG	04061832076522

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