| Identification | Back Directory | [Name]
IPEROXO | [CAS]
247079-84-1 | [Synonyms]
IPEROXO
Iperoxo (iodide)
Iperoxo >=98% (HPLC)
4-[(4,5-Dihydro-3-isoxazolyl)oxy]-N,N,N-trimethyl-2-butyn-1-aminium iodide | [Molecular Formula]
C10H17IN2O2 | [MOL File]
247079-84-1.mol | [Molecular Weight]
324.16 |
| Chemical Properties | Back Directory | [storage temp. ]
2-8°C | [solubility ]
H2O: soluble5mg/mL, clear (warmed) | [form ]
powder | [color ]
white to beige | [Water Solubility ]
H2O: 5mg/mL, clear (warmed) | [InChI]
1S/C9H14N2O2/c1-11(2)6-3-4-7-12-9-5-8-13-10-9/h5-8H2,1-2H3 | [InChIKey]
CADHNBBPGYVTOA-UHFFFAOYSA-N |
| Hazard Information | Back Directory | [Uses]
Iperoxo is a potent superagonist of muscarinic acetylcholine receptor (mAChR) that activates M1, M2 and M3 receptors with pEC50 of 9.87, 10.1 and 9.78. [3H]Iperoxo can be used for direct probing activation-related conformational transitions of muscarinic receptors[1][2]. Iperoxo is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. | [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. | [in vivo]
Iperoxo (0.01 mg/kg, sc, single dose) exhibitis analgesic activity in rats with an ID50 of 1 μg/kg[4].
| [IC 50]
mAChR2: 10.1 (pEC50); mAChR1: 9.87 (pEC50); mAChR3: 9.78 (pEC50) | [References]
[1] Schrage R, et, al. Agonists with supraphysiological efficacy at the muscarinic M2 ACh receptor. Br J Pharmacol. 2013 May;169(2):357-70. DOI:10.1111/bph.12003
[2] Schrage R, et, al. New insight into active muscarinic receptors with the novel radioagonist [3H]iperoxo. Biochem Pharmacol. 2014 Aug 1;90(3):307-19. DOI:10.1016/j.bcp.2014.05.012
[3] Kruse AC, et al., Activation and allosteric modulation of a muscarinic acetylcholine receptor. Nature. 2013 Dec 5;504(7478):101-6. DOI:10.1038/nature12735
[4] Matera C, et al., Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity. Eur J Med Chem. 2014 Mar 21;75:222-32. DOI:10.1016/j.ejmech.2014.01.032 |
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