Natural muscarinic alkaloids

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Muscarine: Muscarine, 2-methyl-3-hydroxy-5-(N,N,N-trimethylammonium) methylente-trahydrofuran chloride (13.1.14), was first isolated from the poisonous mushrooms Amanita muscaria. It can be synthesized in various ways from completely different substances [16-24], 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-dimethylaminomethyltetrahydroflu-rane (13.1.13), the reaction of which with methyl chloride gives muscarine (13.1.14) as a mixture of stereoisomers.

COOCH3 1. h2nnh2 NHCOOCH(CH3)2 o o


H3c o CH3 H3C^O^CH3 H3C^O^CH3 BrCH2^O^~CH3

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 choli-nomimetic 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.

Mushroom poisoning requires serious medical intervention because muscarine absorbs well in the gastrointestinal tract, and therefore it can lead to death. Muscarine is considerably more powerful than acetylcholine, possibly because of its high stability. Because it is

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