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Key Documents

SML0790

Sigma-Aldrich

Iperoxo

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C10H17IN2O2
Numéro CAS:
247079-84-1
Poids moléculaire :
324.16
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

H2O: 5 mg/mL, clear (warmed)

Température de stockage

2-8°C

InChI

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

Clé InChI

CADHNBBPGYVTOA-UHFFFAOYSA-N

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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

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

Muscarinic Acetylcholine Receptors

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

Muscarinic Acetylcholine Receptors

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

Muscarinic Acetylcholine Receptors

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

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