Xanomeline oxalate
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MedKoo CAT#: 526576

CAS#: 141064-23-5

Description: Xanomeline s a muscarinic acetylcholine receptor agonist with reasonable selectivity for the M1 and M4 subtypes, though it is also known to act as a M5 receptor antagonist. It has been studied for the treatment of both Alzheimer's disease and schizophrenia, particularly the cognitive and negative symptoms, although gastrointestinal side effects led to a high drop-out rate in clinical trials. Despite this, xanomeline has been shown to have reasonable efficacy for the treatment of schizophrenia symptoms, and one recent human study found robust improvements in verbal learning and short-term memory associated with xanomeline treatment.


Price and Availability

Size
Price

10mg
USD 285
Size
Price

20mg
USD 550
Size
Price

Xanomeline oxalate, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526576
Name: Xanomeline oxalate
CAS#: 141064-23-5
Chemical Formula: C16H25N3O5S
Exact Mass: 281.1562
Molecular Weight: 371.452
Elemental Analysis: C, 51.74; H, 6.78; N, 11.31; O, 21.54; S, 8.63


Related CAS #: 152854-19-8 (tartrate)   131986-45-3 (free base)   141064-23-5 (oxalate)    

Synonym: LY-246708; LY246708; LY 246708; Xanomeline; Memcor; NNC-110232; Hexyloxy-TZTP; HexyloxyTZTP. Xanomeline oxalate

IUPAC/Chemical Name: 3-(hexyloxy)-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole oxalate

InChi Key: ZJOUESNWCLASJP-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H23N3OS.C2H2O4/c1-3-4-5-6-10-18-14-13(15-19-16-14)12-8-7-9-17(2)11-12;3-1(4)2(5)6/h8H,3-7,9-11H2,1-2H3;(H,3,4)(H,5,6)

SMILES Code: CN1CCC=C(C2=NSN=C2OCCCCCC)C1


Technical Data

Appearance:
White to off-white 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, not in water

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: Vardigan JD, Cannon CE, Puri V, Dancho M, Koser A, Wittmann M, Kuduk SD, Renger JJ, Uslaner JM. Improved cognition without adverse effects: novel M1 muscarinic potentiator compares favorably to donepezil and xanomeline in rhesus monkey. Psychopharmacology (Berl). 2015 Jun;232(11):1859-66. doi: 10.1007/s00213-014-3813-x. Epub 2014 Dec 10. PubMed PMID: 25491927.

2: Rosas-Ballina M, Valdés-Ferrer SI, Dancho ME, Ochani M, Katz D, Cheng KF, Olofsson PS, Chavan SS, Al-Abed Y, Tracey KJ, Pavlov VA. Xanomeline suppresses excessive pro-inflammatory cytokine responses through neural signal-mediated pathways and improves survival in lethal inflammation. Brain Behav Immun. 2015 Feb;44:19-27. doi: 10.1016/j.bbi.2014.07.010. Epub 2014 Jul 23. PubMed PMID: 25063706; PubMed Central PMCID: PMC4624331.

3: Bonifazi A, Yano H, Del Bello F, Farande A, Quaglia W, Petrelli R, Matucci R, Nesi M, Vistoli G, Ferré S, Piergentili A. Synthesis and biological evaluation of a novel series of heterobivalent muscarinic ligands based on xanomeline and 1-[3-(4-butylpiperidin-1-yl)propyl]-1,2,3,4-tetrahydroquinolin-2-one (77-LH-28-1). J Med Chem. 2014 Nov 13;57(21):9065-77. doi: 10.1021/jm501173q. Epub 2014 Oct 16. PubMed PMID: 25275964.

4: Thomsen M, Fulton BS, Caine SB. Acute and chronic effects of the M1/M4-preferring muscarinic agonist xanomeline on cocaine vs. food choice in rats. Psychopharmacology (Berl). 2014 Feb;231(3):469-79. doi: 10.1007/s00213-013-3256-9. Epub 2013 Aug 31. PubMed PMID: 23995301; PubMed Central PMCID: PMC3947149.

5: Baker S, Chin CL, Basso AM, Fox GB, Marek GJ, Day M. Xanomeline modulation of the blood oxygenation level-dependent signal in awake rats: development of pharmacological magnetic resonance imaging as a translatable pharmacodynamic biomarker for central activity and dose selection. J Pharmacol Exp Ther. 2012 Apr;341(1):263-73. doi: 10.1124/jpet.111.188797. Epub 2012 Jan 20. PubMed PMID: 22267203.

6: Zhang X, Gong Q, Zhang S, Wang L, Hu Y, Shen H, Dong S. 3-[3-(3-florophenyl-2-propyn-1-ylthio)-1, 2, 5-thiadiazol-4-yl]-1, 2, 5, 6-tetrahydro-1- methylpyridine oxalate, a novel xanomeline derivative, improves neural cells proliferation and survival in adult mice. Neural Regen Res. 2012 Jan 5;7(1):24-30. doi: 10.3969/j.issn.1673-5374.2012.01.004. PubMed PMID: 25806054; PubMed Central PMCID: PMC4354111.

7: Martino G, Puma C, Yu XH, Gilbert AK, Coupal M, Markoglou N, McIntosh FS, Perkins MN, Laird JM. The M1/M4 preferring agonist xanomeline is analgesic in rodent models of chronic inflammatory and neuropathic pain via central site of action. Pain. 2011 Dec;152(12):2852-60. doi: 10.1016/j.pain.2011.09.017. Epub 2011 Oct 22. PubMed PMID: 22018972.

8: Barak S, Weiner I. The M₁/M₄ preferring agonist xanomeline reverses amphetamine-, MK801- and scopolamine-induced abnormalities of latent inhibition: putative efficacy against positive, negative and cognitive symptoms in schizophrenia. Int J Neuropsychopharmacol. 2011 Oct;14(9):1233-46. doi: 10.1017/S1461145710001549. Epub 2011 Jan 7. PubMed PMID: 21211109.

9: Wang D, Yang L, Su J, Niu Y, Lei X, Xiong J, Cao X, Hu Y, Mei B, Hu JF. Attenuation of neurodegenerative phenotypes in Alzheimer-like presenilin 1/presenilin 2 conditional double knockout mice by EUK1001, a promising derivative of xanomeline. Biochem Biophys Res Commun. 2011 Jul 1;410(2):229-34. doi: 10.1016/j.bbrc.2011.05.120. Epub 2011 May 27. PubMed PMID: 21651893.

10: Dencker D, Wörtwein G, Weikop P, Jeon J, Thomsen M, Sager TN, Mørk A, Woldbye DP, Wess J, Fink-Jensen A. Involvement of a subpopulation of neuronal M4 muscarinic acetylcholine receptors in the antipsychotic-like effects of the M1/M4 preferring muscarinic receptor agonist xanomeline. J Neurosci. 2011 Apr 20;31(16):5905-8. doi: 10.1523/JNEUROSCI.0370-11.2011. PubMed PMID: 21508215.

11: Grant MK, Noetzel MJ, De Lorme KC, Jakubík J, Doležal V, El-Fakahany EE. Pharmacological evaluation of the long-term effects of xanomeline on the M(1) muscarinic acetylcholine receptor. PLoS One. 2010 Dec 23;5(12):e15722. doi: 10.1371/journal.pone.0015722. PubMed PMID: 21203415; PubMed Central PMCID: PMC3009740.

12: Si W, Zhang X, Niu Y, Yu H, Lei X, Chen H, Cao X. A novel derivative of xanomeline improves fear cognition in aged mice. Neurosci Lett. 2010 Apr 5;473(2):115-9. doi: 10.1016/j.neulet.2010.02.031. Epub 2010 Feb 21. PubMed PMID: 20178835.

13: Fang L, Jumpertz S, Zhang Y, Appenroth D, Fleck C, Mohr K, Tränkle C, Decker M. Hybrid molecules from xanomeline and tacrine: enhanced tacrine actions on cholinesterases and muscarinic M1 receptors. J Med Chem. 2010 Mar 11;53(5):2094-103. doi: 10.1021/jm901616h. PubMed PMID: 20158205.

14: Noetzel MJ, Grant MK, El-Fakahany EE. Mechanisms of M3 muscarinic receptor regulation by wash-resistant xanomeline binding. Pharmacology. 2009;83(5):301-17. doi: 10.1159/000214843. Epub 2009 Apr 28. PubMed PMID: 19401618; PubMed Central PMCID: PMC2835379.

15: Noetzel MJ, Grant MK, El-Fakahany EE. Immediate and delayed consequences of xanomeline wash-resistant binding at the M3 muscarinic receptor. Neurochem Res. 2009 Jun;34(6):1138-49. doi: 10.1007/s11064-008-9886-3. Epub 2008 Dec 12. PubMed PMID: 19082883; PubMed Central PMCID: PMC3752336.

16: Cui Y, Wang D, Si W, Lv W, Niu Y, Lei X, Hu Y, Cao X. Enhancement of memory function in aged mice by a novel derivative of xanomeline. Cell Res. 2008 Nov;18(11):1151-3. doi: 10.1038/cr.2008.292. PubMed PMID: 18936783.

17: Kane BE, Grant MK, El-Fakahany EE, Ferguson DM. Synthesis and evaluation of xanomeline analogs--probing the wash-resistant phenomenon at the M1 muscarinic acetylcholine receptor. Bioorg Med Chem. 2008 Feb 1;16(3):1376-92. Epub 2007 Oct 22. PubMed PMID: 17977730.

18: De Lorme KC, Grant MK, Noetzel MJ, Polson SB, El-Fakahany EE. Long-term changes in the muscarinic M1 receptor induced by instantaneous formation of wash-resistant xanomeline-receptor complex. J Pharmacol Exp Ther. 2007 Dec;323(3):868-76. Epub 2007 Sep 12. PubMed PMID: 17855477.

19: Jakubík J, Tucek S, El-Fakahany EE. Allosteric modulation by persistent binding of xanomeline of the interaction of competitive ligands with the M1 muscarinic acetylcholine receptor. J Pharmacol Exp Ther. 2002 Jun;301(3):1033-41. PubMed PMID: 12023535.

20: Frederick Bd, Satlin A, Wald LL, Hennen J, Bodick N, Renshaw PF. Brain proton magnetic resonance spectroscopy in Alzheimer disease: changes after treatment with xanomeline. Am J Geriatr Psychiatry. 2002 Jan-Feb;10(1):81-8. PubMed PMID: 11790638.