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131986-45-3

131986-45-3 Structure

131986-45-3 Structure
IdentificationBack Directory
[Name]

5-(4-HEXYLOXY-[1,2,5]THIADIAZOL-3-YL)-1-METHYL-1,2,3,6-TETRAHYDRO-PYRIDINE
[CAS]

131986-45-3
[Synonyms]

Memcor
Lomeron
LY-246708
XANOMELINE
NNC-11-0232
3-(Hexyloxy)
Xanomeline L-tartrate hydrate
Xanomeline L-tartrate hydrate >=98% (HPLC)
-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)
3-Hexoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)-1,2,5-thiadiazole
3-(Hexyloxy)-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole
5-(4-HEXYLOXY-[1,2,5]THIADIAZOL-3-YL)-1-METHYL-1,2,3,6-TETRAHYDRO-PYRIDINE
3-[4-(Hexy loxy)-1,2,5-thiadiazol-3-y1]-1,2,5,6-tetrahydro-1-methylpyridine
Pyridine, 3-[4-(hexyloxy)-1,2,5-thiadiazol-3-yl]-1,2,5,6-tetrahydro-1-methyl-
5-(4-HEXYLOXY-[1,2,5]THIADIAZOL-3-YL)-1-METHYL-1,2,3,6-TETRAHYDRO-PYRIDINE USP/EP/BP
[Molecular Formula]

C14H23N3OS
[MDL Number]

MFCD00867179
[MOL File]

131986-45-3.mol
[Molecular Weight]

281.42
Chemical PropertiesBack Directory
[Boiling point ]

397.0±42.0 °C(Predicted)
[density ]

1.101±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

H2O: soluble10mg/mL, clear (warmed)
[form ]

powder
[pka]

7.34±0.40(Predicted)
[color ]

off-white
[InChI]

InChI=1S/C14H23N3OS/c1-3-4-5-6-10-18-14-13(15-19-16-14)12-8-7-9-17(2)11-12/h8H,3-7,9-11H2,1-2H3
[InChIKey]

JOLJIIDDOBNFHW-UHFFFAOYSA-N
[SMILES]

C1N(C)CCC=C1C1C(OCCCCCC)=NSN=1
Safety DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)
GHS06
[Signal word ]

Danger
[Hazard statements ]

H301
[Precautionary statements ]

P264-P270-P301+P312-P330
[WGK Germany ]

3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium borohydride-->Iodomethane-->Formamide-->Praseodymium(III) nitrate hexahydrate-->3-Pyridylacetonitrile-->Sodium hexylate
Hazard InformationBack Directory
[Description]

Xanomeline(131986-45-3) acts as a potent and selective muscarinic type 1 and type 4 (M1/M4) receptor agonist to increase neuronal excitability. Xanomeline is used in studies of neurological disorders such as Alzheimer's disease and schizophrenia. However, development of the drug was halted due to severe cholinergic adverse effects. Currently, xanomeline-trospium (KarXT) (a peripheral cholinergic antagonist) has been explored for the treatment of schizophrenia and a New Drug Application has been filed with the FDA, with a decision on whether it will be approved or not expected on 26 September 2024.
[Chemical Properties]

Xanomeline Oxalate: C14H23N3OS?C2H2O4. [141064-23-5]. Crystallized from acetone, melting point 148°C.
(+)-L-Tartrate: C14H23N3OS?C4H6O6. [152854-19-8]. Crystallized from 2-propanol, melting point 95.5°C.
[Uses]

Alzheimer’s disease treatment (cholinergic agonist).
[Definition]

ChEBI: Xanomeline is a member of thiadiazoles and a tetrahydropyridine. It has a role as a muscarinic agonist and a serotonergic agonist.
[Mechanism of action]

Xanomeline's(131986-45-3) mechanism of action is is to rebalance key neurotransmitter circuits, including acetylcholine, dopamine and glutamate, which are disrupted in schizophrenia and related disorders.
[in vivo]

Xanomeline (0.5~3 mg/kg; s.c.; 1~3 hours) induces salivation and vomiting in some monkeys[3].
Xanomeline shows functional dopamine antagonism and an antipsychotic-like profile. Xanomeline inhibits D-amphetamine- and ( )-apomorphine-induced behavior and do not cause extrapyramidal side effects[3].

Animal Model:Male Cebus apella monkeys
Dosage:0.5~3 mg/kg
Administration:S.c.; 1~3 hours
Result:Induced salivation and vomiting in some monkeys.
[IC 50]

mAChR1; mAChR4
Spectrum DetailBack Directory
[Spectrum Detail]

Xanomeline(131986-45-3)1HNMR
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