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T2452

Sigma-Aldrich

Talsaclidine

≥98% (HPLC), oil

Synonym(s):

(R)-3-(2-Propynyloxy)-1-Azabicyclo[2.2.2]octane, WAL 2014

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About This Item

Empirical Formula (Hill Notation):
C10H15NO
CAS Number:
147025-53-4
Molecular Weight:
165.23
UNSPSC Code:
12352204
PubChem Substance ID:
329826707
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

oil

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

SMILES string

C#CCO[C@H]1CN2CC[C@H]1CC2

InChI

1S/C10H15NO/c1-2-7-12-10-8-11-5-3-9(10)4-6-11/h1,9-10H,3-8H2/t10-/m0/s1

InChI key

XVFJONKUSLSKSW-JTQLQIEISA-N

Biochem/physiol Actions

Talsaclidine aids in promoting the nonamyloidogenic α-secretase pathway in model systems.[1] It is more effective in stimulating muscarinic M 1 receptors than M 2 and M 3 receptors.[2] In anesthetized guinea pigs, talsaclidine has no bronchospastic effects, but it produces contracture in isolated tracheal muscle. Talsaclidine is considered a potential candidate for cholinergic replacement therapy.[3]
Talsaclidine is a M1 selective muscarinic receptor agonist. Concentration-dependently, talsaclidine increases the release of APPs and dose-dependently. Talsaclidine decreases Aβ formation and decreases cerebrospinal fluid Aβ in AD patients.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Muscarinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Packaging

Packaged under argon

Preparation Note

Talsaclidine is soluble in DMSO at a concentration that is greater than 5 mg/ml.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
097K4709

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C Hock et al.
Annals of the New York Academy of Sciences, 920, 285-291 (2001-02-24)
Brain amyloid load in Alzheimer's disease (AD) is, at least in genetic forms, associated with overproduction of amyloid beta-peptides (A beta). Thus, lowering A beta production is a central therapeutic target in AD and may be achieved by modulating such
M Wienrich et al.
Life sciences, 68(22-23), 2593-2600 (2001-06-08)
In functional pharmacological assays, talsaclidine has been described as a functionally preferential M1 agonist with full intrinsic activity, and less pronounced effects at M2- and M3 receptors. In accordance with this, cholinomimetic central activation measured in rabbits by EEG recordings
A Walland et al.
European journal of pharmacology, 330(2-3), 213-219 (1997-07-09)
The aim of the present investigation was to determine the reasons why the muscarinic receptor agonist talsaclidine (WAL 2014 FU, 1-azabicyclo[2.2.2] octane,3-(2-propynyloxy)-, (R)-,(E)-2-butenedioate) is devoid of bronchospastic effects in anaesthetized guinea pigs but causes contracture in isolated tracheal muscle from

Articles

Muscarinic Acetylcholine Receptors

Muscarinic acetylcholine receptors mediate acetylcholine actions in CNS and non-nervous tissues, crucial for cell signaling.

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