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SML0790

Sigma-Aldrich

Iperoxo

≥98% (HPLC)

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Synonym(s):
4-[(4,5-Dihydro-3-isoxazolyl)oxy]-N,N,N-trimethyl-2-butyn-1-aminium iodide
Empirical Formula (Hill Notation):
C10H17IN2O2
CAS Number:
Molecular Weight:
324.16
NACRES:
NA.77

Quality Level

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

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Sigma-Aldrich

Sigma-Aldrich

SML0790

Iperoxo

IOX2 ≥98% (HPLC)

Sigma-Aldrich

SML0652

IOX2

BC-LI-0186 ≥98% (HPLC)

Sigma-Aldrich

SML2226

BC-LI-0186

alpha-NETA ≥98% (HPLC)

Sigma-Aldrich

SML2731

alpha-NETA

form

powder

form

powder

form

powder

form

powder

color

white to beige

color

white to beige

color

white to beige

color

white to beige

solubility

H2O: 5 mg/mL, clear (warmed)

solubility

DMSO: 5 mg/mL, clear (warmed)

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

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. 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

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Customers Also Viewed

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
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
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 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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