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M6532

Sigma-Aldrich

(+)-Muscarine chloride

~95% (TLC), powder

Synonym(s):

(+)-(2S,4R,5S)-Tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-2-furanmethanammonium chloride, (+)-Tetrahydro-4β-hydroxy-N,N,N,5α-tetramethyl-2α-furanmethanaminium chloride

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About This Item

Empirical Formula (Hill Notation):
C9H20ClNO2
CAS Number:
2303-35-7
Molecular Weight:
209.71
EC Number:
218-963-2
MDL number:
MFCD00069312
UNSPSC Code:
12352200
PubChem Substance ID:
24897094
NACRES:
NA.77

assay

~95% (TLC)

Quality Level

200

form

powder

color

white

solubility

H2O: 50 mg/mL

SMILES string

[Cl-].C[C@@H]1O[C@@H](C[C@H]1O)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/t7-,8-,9+;/m0./s1

InChI key

WUFRNEJYZWHXLC-CTERPIQNSA-M

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Biochem/physiol Actions

Prototype muscarinic acetylcholine receptor agonist; active enantiomer.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
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.

Caution

Extremely hygroscopic

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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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A G Karczmar
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 9(3), 181-199 (1993-11-01)
This year marks the seventieth anniversary of Otto Loewi's demonstration of chemical transmission generally and autonomic cholinergic transmission specifically and the fortieth anniversary of John Eccles's proof of the existence of central cholinergic transmission. Following these epochal findings, the subsequent
F J Evans
Journal of ethnopharmacology, 32(1-3), 91-101 (1991-04-01)
One traditional aspect of natural products in medical research has been their use in the identification and investigation of the physiological/pathological role of receptors and enzymes as possible targets for drug design programmes. Classical examples of this function of natural
I Slutsky et al.
The Journal of physiology, 514 ( Pt 3), 769-782 (1999-01-12)
1. Presynaptic effects of muscarine on neurotransmitter release were studied at the frog neuromuscular junction, using focal depolarization of the presynaptic terminal to different levels. 2. Muscarine (10 microM) had a dual effect on ACh release: concomitant inhibition and enhancement
A E Stewart et al.
Journal of neurophysiology, 81(1), 72-84 (1999-01-23)
We used the whole cell patch-clamp technique and single-cell reverse transcription-polymerase chain reaction (RT-PCR) to study the muscarinic receptor-mediated modulation of calcium channel currents in both acutely isolated and cultured pyramidal neurons from rat sensorimotor cortex. Single-cell RT-PCR profiling for
Alfonso Claros-Guzmán et al.
Journal of comparative physiology. A, Neuroethology, sensory, neural, and behavioral physiology, 206(6), 857-870 (2020-09-22)
Many relevant aspects of mammal's cardiac physiology have been mainly investigated in insect models such as Drosophila melanogaster and Periplaneta americana. Cardiac function has been poorly studied in the cockroach Gromphadorhina portentosa, which has some advantages for experimental purposes such
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