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A9101

Sigma-Aldrich

Acetylcholine chloride

≥99% (TLC), powder or crystals

Synonym(s):

ACh

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About This Item

Linear Formula:
(CH3)3N+CH2CH2OCOCH3Cl-
CAS Number:
60-31-1
Molecular Weight:
181.66
Beilstein/REAXYS Number:
3571875
EC Number:
200-468-8
MDL number:
MFCD00011698
UNSPSC Code:
12352204
PubChem Substance ID:
57653883
NACRES:
NA.32

product name

Acetylcholine chloride, pkg of 150 mg (per vial)

assay

≥99% (TLC)

Quality Level

100

form

powder or crystals

packaging

pkg of 150 mg (per vial)

mp

146-150 °C (lit.)

solubility

H2O: soluble

storage temp.

room temp

SMILES string

[Cl-].CC(=O)OCC[N+](C)(C)C

InChI

1S/C7H16NO2.ClH/c1-7(9)10-6-5-8(2,3)4;/h5-6H2,1-4H3;1H/q+1;/p-1

InChI key

JUGOREOARAHOCO-UHFFFAOYSA-M

Gene Information

human ... CHRM3(1131)

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General description

Acetylcholine is an important neurotransmitter that plays a critical role in multiple neurological systems. Crucial for neurobiology studies, acetylcholine aids researchers in understanding synaptic transmission. In other forms of research, acetylcholine has an effect and influence on tumor neurobiology for cancer R&D, as well as a variety of other cognitive processes.

Application

For use as a substrate to determine acetylcholinesterase activity. Acetylcholine chloride has been used:
  • for standard curve preparation in hestrin assay
  • in Protein expression, radioactive ligand binding assay and electrophysiological studies of Lymnaea stagnalis acetylcholine binding protein (Ls-AChBPs)
  • as a supplement in extracellular solutions for treating the voltage clamped cells in electrophysiology studies

Biochem/physiol Actions

Acetyl choline (ACh) is an essential neurotransmitter in both central and peripheral nervous system. ACh binds to nicotinic acetylcholine receptors (nAChRs) and causes fast excitatory neurotransmission.
Acetylcholine chloride, injected at 20 mg/kg body weight, reduces mortality and plasma proinflammatory cytokines in mice with experimentally-induced sepsis . The cholinergic anti-inflammatory mechanism is probably mediated by interaction of acetylcholine with α7n cholinoreceptor on monocytes, macrophages, and neutrophils, which decreases the levels of proinflammatory cytokines such as TNF-α, IL-1β, and IL-6.

Reconstitution

Reconstituted solution is stable for 2 weeks when stored at 2-8 °C

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Evaluation of two WHO First International Standards for Vi polysaccharide from Citrobacter freundii and Salmonella enterica subspecies enterica serovar Typhi.
Gao F, et al.
Biologicals : Journal of the International Association of Biological Standardization (2018)
Molecular recognition of the neurotransmitter acetylcholine by an acetylcholine binding protein reveals determinants of binding to nicotinic acetylcholine receptors.
Olsen JA, et al.
PloS one, 9(3), e91232-e91232 (2014)
Ancestral Reconstruction Approach to Acetylcholine Receptor Structure and Function.
Prinston JE, et al.
Structure, 25(8), 1295-1302 (2017)
Tracey Huynh et al.
Journal of medicinal chemistry, 56(20), 8196-8200 (2013-10-01)
The M4 mAChR is implicated in several CNS disorders and possesses an allosteric binding site for which ligands modulating the affinity and/or efficacy of ACh may be exploited for selective receptor targeting. We report the synthesis of a focused library
Elim Hong et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(52), 21171-21176 (2013-12-12)
The habenulo-interpeduncular pathway, a highly conserved cholinergic system, has emerged as a valuable model to study left-right asymmetry in the brain. In larval zebrafish, the bilaterally paired dorsal habenular nuclei (dHb) exhibit prominent left-right differences in their organization, gene expression
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