3-[4-(Hexyloxy)-1,2,5-thiadiazol-3-yl]-1,2,5,6-tetrahydro-1-methylpyridineoxalate

Product Name3-[4-(Hexyloxy)-1,2,5-thiadiazol-3-yl]-1,2,5,6-tetrahydro-1-methylpyridineoxalate
CAS141064-23-5
MFC14H23N3OS.C2H2O4
MW371
EINECS
MOL File141064-23-5.mol

Chemical Properties

Melting point	148-150℃
storage temp.	Desiccate at +4°C
solubility	DMF: 1.6 mg/ml; DMF:PBS (pH 7.2) (1:9): 0.1 mg/ml
form	Powder
color	White to off-white
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)
InChIKey	ZJOUESNWCLASJP-UHFFFAOYSA-N
SMILES	[s]1nc(c(n1)C2=CCCN(C2)C)OCCCCCC.OC(=O)C(=O)O

Safety Information

WGK Germany	WGK 3
Storage Class	6.1C - Combustible, acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral

Usage And Synthesis

Description

Muscarinic receptors are G protein-coupled acetylcholine receptors that play diverse roles. Xanomeline (oxalate) is a potent agonist of muscarinic acetylcholine receptors (EC₅₀ values are 0.3, 92.5, 5, 52, and 42 nM for M₁, M₂, M₃, M₄, and M₅, respectively). It has antipsychotic-like activities in rats and Cebus monkeys. M₁ selective agonists, like Xanomeline (oxalate), enhance memory function and has utility in treating Alzheimer’s Disease.

Uses

Xanomeline oxalate is a functionally selective mAChR M1 agonist.

in vivo

Xanomeline robustly stimulates in vivo PI hydrolysis and the effect is blocked by muscarinic antagonists, demonstrating mediation by muscarinic receptors. In mice the ED₁₀₀ for Xanomeline-induced stimulation of [³H]-IP accumulation is 54 μmole/kg in hippocampus. And in rats the ED₁₀₀ for Xanomeline-induced stimulation of [³H]-IP accumulation is 8.1 μmole/kg in hippocampus^[1].

Animal Model:	Male CF1 mice weighing 18-20 g are injected [³H]-myoinositol^[1]
Dosage:	8.1-81 μmole/kg
Administration:	S.c. injections; 1 h prior to killing and 1 h after the administration
Result:	Increased accumulation in a dose-related manner up to 130%, 75%, 60% above lithium levels in hippocampus, cortex and neostriatum, respectively. And did not increase accumulation of [³H]-IP in the brain stem. Induced salivation, tremor and hypothermia in mice with the ED₅₀ of 13.7±0.8 μmole/kg.

Animal Model:	Rats are injected [³H]-myoinositol^[1]
Dosage:	2.7-81 μmole/kg
Administration:	S.c. injections; 1 h prior to killing and 1 h after the administration
Result:	Increased [³H]-IP formation dose dependently in hippocampus up to 221% above lithium control.

storage

Desiccate at +4°C

References

[1] JULIA N. HEINRICH . Pharmacological comparison of muscarinic ligands: Historical versus more recent muscarinic M1-preferring receptor agonists[J]. European journal of pharmacology, 2009, 605 1: Pages 53-56. DOI: 10.1016/j.ejphar.2008.12.044
[2] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[3] MAIBRITT B ANDERSEN. The Muscarinic M1/M4 Receptor Agonist Xanomeline Exhibits Antipsychotic-Like Activity in Cebus apella Monkeys[J]. Neuropsychopharmacology, 2003, 28 6: 1168-1175. DOI: 10.1038/sj.npp.1300151
[4] MESSER W S. The utility of muscarinic agonists in the treatment of alzheimer’s disease[J]. Journal of Molecular Neuroscience, 2002, 19 1-2: 187-193. DOI: 10.1007/s12031-002-0031-5

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