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MedKoo Cat#: 563321 | Name: Iperoxo
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Iperoxo is a superagonist of the muscarinic acetylcholine receptors and an OxotremorineM analog.

Chemical Structure

Iperoxo
Iperoxo
CAS#247079-84-1

Theoretical Analysis

MedKoo Cat#: 563321

Name: Iperoxo

CAS#: 247079-84-1

Chemical Formula: C9H14N2O2

Exact Mass: 182.1055

Molecular Weight: 182.22

Elemental Analysis: C, 59.32; H, 7.74; N, 15.37; O, 17.56

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
25mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Iperoxo;
IUPAC/Chemical Name
4-[(4,5-Dihydro-3-isoxazolyl)oxy]-N,N,N-trimethyl-2-butyn-1-aminium iodide
InChi Key
XWEOIAMCTHLJJB-UHFFFAOYSA-M
InChi Code
InChI=1S/C10H17N2O2.HI/c1-12(2,3)7-4-5-8-13-10-6-9-14-11-10;/h6-9H2,1-3H3;1H/q+1;/p-1
SMILES Code
C[N+](C)(C)CC#CCOC1=NOCC1.[I-]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Iperoxo is a potent superagonist of muscarinic acetylcholine receptor (mAChR).
In vitro activity:
In CHO-hM2 cells, iperoxo significantly exceeds ACh in Gi /Gs signalling competence. In the orthosteric loss-of-function mutant M2 -Y104(3.33) A, the maximum effect of iperoxo is hardly compromised in contrast to ACh. Reference: Br J Pharmacol. 2013 May;169(2):357-70. https://pubmed.ncbi.nlm.nih.gov/23062057/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 182.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Schrage R, Seemann WK, Klöckner J, Dallanoce C, Racké K, Kostenis E, De Amici M, Holzgrabe U, Mohr K. Agonists with supraphysiological efficacy at the muscarinic M2 ACh receptor. Br J Pharmacol. 2013 May;169(2):357-70. doi: 10.1111/bph.12003. PMID: 23062057; PMCID: PMC3651662.
In vitro protocol:
1. Schrage R, Seemann WK, Klöckner J, Dallanoce C, Racké K, Kostenis E, De Amici M, Holzgrabe U, Mohr K. Agonists with supraphysiological efficacy at the muscarinic M2 ACh receptor. Br J Pharmacol. 2013 May;169(2):357-70. doi: 10.1111/bph.12003. PMID: 23062057; PMCID: PMC3651662.
In vivo protocol:
TBD
1: Jiménez-Rosés M, Matsoukas MT, Caltabiano G, Cordomí A. Ligand-Triggered Structural Changes in the M(2) Muscarinic Acetylcholine Receptor. J Chem Inf Model. 2018 May 29;58(5):1074-1082. doi: 10.1021/acs.jcim.8b00108. Epub 2018 May 2. PubMed PMID: 29671585. 2: Fish I, Stößel A, Eitel K, Valant C, Albold S, Huebner H, Möller D, Clark MJ, Sunahara RK, Christopoulos A, Shoichet BK, Gmeiner P. Structure-Based Design and Discovery of New M(2) Receptor Agonists. J Med Chem. 2017 Nov 22;60(22):9239-9250. doi: 10.1021/acs.jmedchem.7b01113. Epub 2017 Nov 13. PubMed PMID: 29094937; PubMed Central PMCID: PMC5836741. 3: Engelhardt B, Holze J, Elliott C, Baillie GS, Kschischo M, Fröhlich H. Modelling and mathematical analysis of the M$_{2}$ receptor-dependent joint signalling and secondary messenger network in CHO cells. Math Med Biol. 2017 May 15. doi: 10.1093/imammb/dqx003. [Epub ahead of print] PubMed PMID: 28505258. 4: Messerer R, Kauk M, Volpato D, Alonso Canizal MC, Klöckner J, Zabel U, Nuber S, Hoffmann C, Holzgrabe U. FRET Studies of Quinolone-Based Bitopic Ligands and Their Structural Analogues at the Muscarinic M(1) Receptor. ACS Chem Biol. 2017 Mar 17;12(3):833-843. doi: 10.1021/acschembio.6b00828. Epub 2017 Feb 6. PubMed PMID: 28117571. 5: Miao Y, McCammon JA. Graded activation and free energy landscapes of a muscarinic G-protein-coupled receptor. Proc Natl Acad Sci U S A. 2016 Oct 25;113(43):12162-12167. Epub 2016 Oct 10. PubMed PMID: 27791003; PubMed Central PMCID: PMC5087018. 6: Chen X, Klöckner J, Holze J, Zimmermann C, Seemann WK, Schrage R, Bock A, Mohr K, Tränkle C, Holzgrabe U, Decker M. Rational design of partial agonists for the muscarinic m1 acetylcholine receptor. J Med Chem. 2015 Jan 22;58(2):560-76. doi: 10.1021/jm500860w. Epub 2014 Dec 19. PubMed PMID: 25478907. 7: Schrage R, Holze J, Klöckner J, Balkow A, Klause AS, Schmitz AL, De Amici M, Kostenis E, Tränkle C, Holzgrabe U, Mohr K. 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. Epub 2014 May 23. PubMed PMID: 24863257. 8: Croy CH, Schober DA, Xiao H, Quets A, Christopoulos A, Felder CC. Characterization of the novel positive allosteric modulator, LY2119620, at the muscarinic M(2) and M(4) receptors. Mol Pharmacol. 2014 Jul;86(1):106-15. doi: 10.1124/mol.114.091751. Epub 2014 May 7. PubMed PMID: 24807965. 9: Matera C, Flammini L, Quadri M, Vivo V, Ballabeni V, Holzgrabe U, Mohr K, De Amici M, Barocelli E, Bertoni S, Dallanoce C. 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. Epub 2014 Jan 25. PubMed PMID: 24534538. 10: Kruse AC, Ring AM, Manglik A, Hu J, Hu K, Eitel K, Hübner H, Pardon E, Valant C, Sexton PM, Christopoulos A, Felder CC, Gmeiner P, Steyaert J, Weis WI, Garcia KC, Wess J, Kobilka BK. Activation and allosteric modulation of a muscarinic acetylcholine receptor. Nature. 2013 Dec 5;504(7478):101-6. doi: 10.1038/nature12735. Epub 2013 Nov 20. PubMed PMID: 24256733; PubMed Central PMCID: PMC4020789. 11: Langmead CJ, Christopoulos A. Supra-physiological efficacy at GPCRs: superstition or super agonists? Br J Pharmacol. 2013 May;169(2):353-6. doi: 10.1111/bph.12142. PubMed PMID: 23441648; PubMed Central PMCID: PMC3651661. 12: Schrage R, Seemann WK, Klöckner J, Dallanoce C, Racké K, Kostenis E, De Amici M, Holzgrabe U, Mohr K. Agonists with supraphysiological efficacy at the muscarinic M2 ACh receptor. Br J Pharmacol. 2013 May;169(2):357-70. doi: 10.1111/bph.12003. PubMed PMID: 23062057; PubMed Central PMCID: PMC3651662.