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M104

Sigma-Aldrich

(±)-Muscarine chloride hydrate

≥98% (HPLC)

Synonym(s):

Tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-2-furanmethanammonium chloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C9H20ClNO2 · xH2O
CAS Number:
2936-25-6
Molecular Weight:
209.71 (anhydrous basis)
MDL number:
MFCD00055067
UNSPSC Code:
12352200
PubChem Substance ID:
24278578
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

deionized water: ≥20 mg/mL

storage temp.

room temp

SMILES string

[Cl-].CC1OC(CC1O)C[N+](C)(C)C

InChI

1S/C9H20NO2.ClH/c1-7-9(11)5-8(12-7)6-10(2,3)4;/h7-9,11H,5-6H2,1-4H3;1H/q+1;/p-1

InChI key

WUFRNEJYZWHXLC-UHFFFAOYSA-M

Gene Information

human ... CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133)

Application

(±)-Muscarine chloride hydrate may be used:
  • as an acetylcholine receptor agonist in neuronal precursor cell lines PC 12 cells
  • as toxin test compound for paper spray mass spectrometry (PSMS) optimization experiments
  • as a component of quality control(QC) in hydrophilic interaction liquid chromatography-high resolution tandem mass spectrometry (HILIC-HRMS/MS) analysis of human urine samples

Biochem/physiol Actions

Muscarine is a potent agonist than acetylcholine and is not susceptible to degradation by cholinesterases. Muscarine administration results in muscle spasm especially in gut, bronchus and uterus.
Muscarinic acetylcholine receptor agonist; originally isolated from Amanita muscaria.

Features and Benefits

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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Chapter 67 - Mushroom Toxins
Puschner B
Veterinary Toxicology, 955-966 (2018)
P J FRASER
British journal of pharmacology and chemotherapy, 12(1), 47-52 (1957-03-01)
The action of chromatographically pure crystalline muscarine chloride, prepared from Amanita muscaria, has been compared with acetylcholine chloride (ACh) on a number of different organs from a variety of species. Muscarine caused spasm in vivo and in vitro of muscles
Thomas P Bambauer et al.
Talanta, 204, 677-684 (2019-07-31)
Paper spray mass spectrometry (PSMS) is currently used in different analytical fields, but less effort has been made so far to use PSMS for highly polar compounds. Such analytes usually show poor performance in PSMS due to their high affinity
Two-dimensional surface plasmon resonance imaging system for cellular analysis
Biosensors and Biodetection, 12(1), 47-52 (2017)
Thomas P Bambauer et al.
Talanta, 213, 120847-120847 (2020-03-24)
The analytical proof of a toxic mushroom and/or plant ingestion at an early stage of a suspected intoxication can be crucial for fast therapeutic decision making. Therefore, comprehensive analytical procedures need to be available. This study aimed to develop a
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