Xamoterol

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

MedKoo CAT#: 341300

CAS#: 81801-12-9

Description: Xamoterol is a cardiac stimulant.


Price and Availability

Size
Price

Size
Price

Size
Price

Xamoterol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 341300
Name: Xamoterol
CAS#: 81801-12-9
Chemical Formula: C16H25N3O5
Exact Mass: 339.1794
Molecular Weight: 339.392
Elemental Analysis: C, 56.62; H, 7.43; N, 12.38; O, 23.57


Synonym: Xamoterol; Xamoterolum.

IUPAC/Chemical Name: 4-Morpholinecarboxamide, N-(2-((2-hydroxy-3-(4-hydroxyphenoxy)propyl)amino)ethyl)-, (+-)-

InChi Key: DXPOSRCHIDYWHW-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H25N3O5/c20-13-1-3-15(4-2-13)24-12-14(21)11-17-5-6-18-16(22)19-7-9-23-10-8-19/h1-4,14,17,20-21H,5-12H2,(H,18,22)

SMILES Code: Oc1ccc(OCC(O)CNCCNC(N2CCOCC2)=O)cc1


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Nasehi M, Shahbazzadeh S, Ebrahimi-Ghiri M, Zarrindast MR. Bidirectional influence of amygdala β(1)-adrenoceptors blockade on cannabinoid signaling in contextual and auditory fear memory. J Psychopharmacol. 2018 Mar 1:269881118760654. doi: 10.1177/0269881118760654. [Epub ahead of print] PubMed PMID: 29580129.

2: Ardestani PM, Evans AK, Yi B, Nguyen T, Coutellier L, Shamloo M. Modulation of neuroinflammation and pathology in the 5XFAD mouse model of Alzheimer's disease using a biased and selective beta-1 adrenergic receptor partial agonist. Neuropharmacology. 2017 Apr;116:371-386. doi: 10.1016/j.neuropharm.2017.01.010. Epub 2017 Jan 13. PubMed PMID: 28089846; PubMed Central PMCID: PMC5385159.

3: Xu D, Wang S, Wu TT, Wang XY, Qian J, Guo Y. Functional cross-talk between the α1- and β1-adrenergic receptors modulates the rapidly activating delayed rectifier potassium current in guinea pig ventricular myocytes. Int J Mol Sci. 2014 Aug 15;15(8):14220-33. doi: 10.3390/ijms150814220. Erratum in: Int J Mol Sci. 2014;15(9):15766. PubMed PMID: 25196520; PubMed Central PMCID: PMC4159847.

4: Torkaman-Boutorabi A, Hashemi-Hezaveh SM, Sheidadoust H, Zarrindast MR. The possible role of medial prefrontal cortex beta-1-adrenoceptors in morphine-induced amnesia. Pharmacology. 2014;93(5-6):272-7. doi: 10.1159/000362282. Epub 2014 Aug 5. PubMed PMID: 25096537.

5: Coutellier L, Ardestani PM, Shamloo M. β1-adrenergic receptor activation enhances memory in Alzheimer's disease model. Ann Clin Transl Neurol. 2014 May 1;1(5):348-360. PubMed PMID: 24883337; PubMed Central PMCID: PMC4036739.

6: Wang S, Xu D, Wu TT, Guo Y, Chen YH, Zou JG. β1-adrenergic regulation of rapid component of delayed rectifier K+ currents in guinea-pig cardiac myocytes. Mol Med Rep. 2014 May;9(5):1923-8. doi: 10.3892/mmr.2014.2035. Epub 2014 Mar 10. PubMed PMID: 24626297.

7: Day JS, O'Neill E, Cawley C, Aretz NK, Kilroy D, Gibney SM, Harkin A, Connor TJ. Noradrenaline acting on astrocytic β₂-adrenoceptors induces neurite outgrowth in primary cortical neurons. Neuropharmacology. 2014 Feb;77:234-48. doi: 10.1016/j.neuropharm.2013.09.027. Epub 2013 Oct 12. PubMed PMID: 24126345.

8: Huet J, Teinkela Mbosso EJ, Soror S, Meyer F, Looze Y, Wintjens R, Wohlkönig A. High-resolution structure of a papaya plant-defense barwin-like protein solved by in-house sulfur-SAD phasing. Acta Crystallogr D Biol Crystallogr. 2013 Oct;69(Pt 10):2017-26. doi: 10.1107/S0907444913018015. Epub 2013 Sep 20. PubMed PMID: 24100320.

9: Vaniotis G, Glazkova I, Merlen C, Smith C, Villeneuve LR, Chatenet D, Therien M, Fournier A, Tadevosyan A, Trieu P, Nattel S, Hébert TE, Allen BG. Regulation of cardiac nitric oxide signaling by nuclear β-adrenergic and endothelin receptors. J Mol Cell Cardiol. 2013 Sep;62:58-68. doi: 10.1016/j.yjmcc.2013.05.003. Epub 2013 May 17. PubMed PMID: 23684854; PubMed Central PMCID: PMC3735468.

10: Reina S, Ganzinelli S, Sterin-Borda L, Borda E. Pro-apoptotic effect of anti-β1-adrenergic receptor antibodies in periodontitis patients. Int Immunopharmacol. 2012 Dec;14(4):710-21. doi: 10.1016/j.intimp.2012.10.011. Epub 2012 Oct 25. PubMed PMID: 23103827.

11: Takayanagi Y, Osawa S, Ikuma M, Takagaki K, Zhang J, Hamaya Y, Yamada T, Sugimoto M, Furuta T, Miyajima H, Sugimoto K. Norepinephrine suppresses IFN-γ and TNF-α production by murine intestinal intraepithelial lymphocytes via the β₁ adrenoceptor. J Neuroimmunol. 2012 Apr;245(1-2):66-74. doi: 10.1016/j.jneuroim.2012.02.007. Epub 2012 Mar 6. PubMed PMID: 22398028.

12: Schutsky K, Ouyang M, Thomas SA. Xamoterol impairs hippocampus-dependent emotional memory retrieval via Gi/o-coupled β2-adrenergic signaling. Learn Mem. 2011 Aug 30;18(9):598-604. doi: 10.1101/lm.2302811. Print 2011. PubMed PMID: 21878527; PubMed Central PMCID: PMC3166789.

13: Baker JG, Kemp P, March J, Fretwell L, Hill SJ, Gardiner SM. Predicting in vivo cardiovascular properties of β-blockers from cellular assays: a quantitative comparison of cellular and cardiovascular pharmacological responses. FASEB J. 2011 Dec;25(12):4486-97. doi: 10.1096/fj.11-192435. Epub 2011 Aug 24. PubMed PMID: 21865315; PubMed Central PMCID: PMC3371235.

14: Faizi M, Bader PL, Tun C, Encarnacion A, Kleschevnikov A, Belichenko P, Saw N, Priestley M, Tsien RW, Mobley WC, Shamloo M. Comprehensive behavioral phenotyping of Ts65Dn mouse model of Down syndrome: activation of β1-adrenergic receptor by xamoterol as a potential cognitive enhancer. Neurobiol Dis. 2011 Aug;43(2):397-413. doi: 10.1016/j.nbd.2011.04.011. Epub 2011 Apr 17. PubMed PMID: 21527343; PubMed Central PMCID: PMC3539757.

15: Cruickshank JM. Beta-blockers and heart failure. Indian Heart J. 2010 Mar-Apr;62(2):101-10. Review. PubMed PMID: 21180298.

16: Panjala SR, Steinle JJ. Insulin and β-adrenergic receptors inhibit retinal endothelial cell apoptosis through independent pathways. Neurochem Res. 2011 Apr;36(4):604-12. doi: 10.1007/s11064-010-0303-3. Epub 2010 Oct 30. PubMed PMID: 21053068.

17: Salehi A, Faizi M, Colas D, Valletta J, Laguna J, Takimoto-Kimura R, Kleschevnikov A, Wagner SL, Aisen P, Shamloo M, Mobley WC. Restoration of norepinephrine-modulated contextual memory in a mouse model of Down syndrome. Sci Transl Med. 2009 Nov 18;1(7):7ra17. doi: 10.1126/scitranslmed.3000258. PubMed PMID: 20368182.

18: Barbatelli G, Murano I, Madsen L, Hao Q, Jimenez M, Kristiansen K, Giacobino JP, De Matteis R, Cinti S. The emergence of cold-induced brown adipocytes in mouse white fat depots is determined predominantly by white to brown adipocyte transdifferentiation. Am J Physiol Endocrinol Metab. 2010 Jun;298(6):E1244-53. doi: 10.1152/ajpendo.00600.2009. Epub 2010 Mar 30. PubMed PMID: 20354155.

19: Uhiara CO, Alexander SP, Roberts RE. Effect of inhibition of extracellular signal-regulated kinase on relaxations to beta-adrenoceptor agonists in porcine isolated blood vessels. Br J Pharmacol. 2009 Dec;158(7):1713-9. doi: 10.1111/j.1476-5381.2009.00435.x. PubMed PMID: 19912229; PubMed Central PMCID: PMC2801212.

20: Yalcin I, Tessier LH, Petit-Demoulière N, Waltisperger E, Hein L, Freund-Mercier MJ, Barrot M. Chronic treatment with agonists of beta(2)-adrenergic receptors in neuropathic pain. Exp Neurol. 2010 Jan;221(1):115-21. doi: 10.1016/j.expneurol.2009.10.008. Epub 2009 Oct 17. PubMed PMID: 19840789.