(+/-)-MUSCARINE CHLORIDE Chemical Properties

storage temp. 

room temp

solubility 

deionized water: ≥20mg/mL

form 

powder

color 

white

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26-36

RIDADR 

1544

WGK Germany 

3

HazardClass 

6.1(a)

PackingGroup 

II

MSDS

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(+/-)-MUSCARINE CHLORIDE Usage And Synthesis

Description

Muscarine is a natural alkaloid that is found in a number of wild mushrooms. Despite the fact that muscarine does not have any therapeutic value, it is of interest because of its expressed toxic properties, which made it one of the first systematically studied cholinomimetic substances. This compound was an underlying classification of cholinergic muscarinic receptors. The action of muscarine is similar to that of acetylcholine on peripheral autonomic effector organs, and atropine is an antagonist to it. Unlike acetylcholine, muscarine does not act on nicotinic receptors.

Uses

(+/-)-Muscarine Chloride is a muscarinic acteylcholine receptor agonist.

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.

Synthesis

Muscarine, 2-methyl-3-hydroxy-5-(N,N,N-trimethylammonium) methylentetrahydrofuran chloride (13.1.14), was first isolated from the poisonous mushrooms Amanita muscaria. It can be synthesized in various ways from completely different substances [16¨C24], particularly from 2,5-dimethyl-3-carboxymethylflurane, which undergoes a Curtius reaction, i.e. successive reactions with hydrazine and further with nitrous acid in isopropyl alcohol, which forms the urethane (13.1.9), the acidic hydrolysis of which gives 2,5-dimethyl-2H-furane-3 (13.1.10). Allylic bromination of this gives 2- methyl-5-bromomethyl-2H-furanone-3 (13.1.11), which is reacted with dimethylamine, forming 2-methyl-5-dimethylaminomethyl-2H-fluranone-3 (13.1.12). Reducing this compound leads to formation of 2-methyl-3-hydroxy-5-dimethylaminomethyltetrahydroflurane (13.1.13), the reaction of which with methyl chloride gives muscarine (13.1.14) as a mixture of stereoisomers.

(+/-)-MUSCARINE CHLORIDE(2936-25-6)Related Product Information

• (+)-MUSCARINE CHLORIDE
• N-METHYLTETRAHYDROFURFURYLAMINE
• β-Methylcholine Chloride
• (+/-)-MUSCARINE CHLORIDE
• (+/-)-MUSCARINE CHLORIDE
• 2-Tetrahydrofurfurylamine