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Xanomeline

Xanomeline structure

CAS No:
131986-45-3
Formula:
C14H23N3OS
Chemical Name:
Xanomeline
Synonyms:
Pyridine,3-[4-(hexyloxy)-1,2,5-thiadiazol-3-yl]-1,2,5,6-tetrahydro-1-methyl-;1,2,5-Thiadiazole,pyridine deriv.;3-[4-(Hexyloxy)-1,2,5-thiadiazol-3-yl]-1,2,5,6-tetrahydro-1-methylpyridine;LY 246708;Xanomeline;3-Hexoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)-1,2,5-thiadiazole
Categories:
Active Pharmaceutical Ingredients > Respiratory Drugs

Description

Xanomeline is a member of thiadiazoles and a tetrahydropyridine. It has a role as a muscarinic agonist and a serotonergic agonist.|Xanomeline is under investigation in clinical trial NCT02831231 (Pilot Study Comparing Effects of Xanomeline Alone to Xanomeline Plus Trospium).

Xanomeline Basic Attributes

Molecular Weight：

281.42

Exact Mass：

281.42

UNII：

9ORI6L73CJ

DSSTox ID：

DTXSID60157286

HScode：

2934999090

Characteristics

PSA：

66.5

XLogP3：

3.3

Appearance：

off-white

Density：

1.101±0.06 g/cm3(Predicted)

Boiling Point：

397.0±42.0 °C(Predicted)

Flash Point：

193.9ºC

Refractive Index：

1.537

Water Solubility：

H2O: soluble10mg/mL, clear (warmed)

Storage Conditions：

2-8°C

Vapor Pressure：

1.64E-06mmHg at 25°C

Safety Information

wgk germany：

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate. (See all compounds classified as Muscarinic Agonists.)|A loosely defined grouping of drugs that have effects on psychological function. Here the psychotropic agents include the antidepressive agents, hallucinogens, and tranquilizing agents (including the antipsychotics and anti-anxiety agents). (See all compounds classified as Psychotropic Drugs.)|Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)

MeSH Entry Terms：

(3-O-hexyloxy)-TZTP

Xanomeline Use and Manufacturing

Methods of Manufacturing

A solution of NaBH4 (273mg, 7.20mmol) in 3mL of MeOH was added dropwise to a solution of 14 (730mg, 1.80mmol) in 5mL of MeOH. The reaction was kept under stirring at room temperature for 2.5days. After quenching with 10mL of water, the aqueous phase was extracted with DCM (3×10mL). The pooled organic phases were dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The crude was purified through silica gel column chromatography, using as eluent DCM/MeOH 95:5. Xanomeline 3 was obtained as a yellow-orange oil (383mg, 75%): Rf=0.30 (DCM/MeOH 95:5). 1H NMR (300MHz, CDCl3): delta 7.16-6.96 (m, 1H; H4?), 4.44 (t, J=6.6Hz, 2H; CH2-O), 3.51 (d, J=2.0Hz, 2H; H2?), 2.63 (t, J=5.7Hz, 2H; H6?), 2.50 (s, 5H; CH3-N, 2×H5?), 1.83 (quint, J=6.9Hz, 2H; CH2-CH2-O), 1.58-1.12 (m, 6H; CH3-CH2-CH2-CH2-(CH2)2-O), 0.90 (t, J=6.6Hz, 3H; CH3-(CH2)5-O). 13C NMR (75MHz, CDCl3): delta 162.49, 146.55, 128.86, 128.18, 70.93, 54.74, 51.08, 45.68, 31.34, 28.76, 26.28, 25.60, 22.48, 13.94.General procedure: The reaction was conducted under Argon atmosphere. To a solution of General procedure: The reaction was conducted under Argon atmosphere. To a solution of General procedure: The reaction was conducted under Argon atmosphere.

Uses

Alzheimer’s disease treatment (cholinergic agonist).

Computed Properties

Molecular Weight:281.42
XLogP3:3.3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:281.15618354
Monoisotopic Mass:281.15618354
Topological Polar Surface Area:66.5
Heavy Atom Count:19
Complexity:298
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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