2936-25-6 Usage
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 [16–24], 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-dimethylaminomethyltetrahydroflurane (13.1.13), the reaction of which with methyl chloride gives muscarine (13.1.14) as a
mixture of stereoisomers.
Check Digit Verification of cas no
The CAS Registry Mumber 2936-25-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,9,3 and 6 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2936-25:
(6*2)+(5*9)+(4*3)+(3*6)+(2*2)+(1*5)=96
96 % 10 = 6
So 2936-25-6 is a valid CAS Registry Number.
InChI:InChI=1/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
2936-25-6Relevant articles and documents
TOTAL SYNTHESIS OF THE MUSCARINES
Pirrung, Michael C.,DeAmicis, Carl V.
, p. 159 - 162 (2007/10/02)
The total syntheses of racemic muscarine and allo-muscarine have been achieved using as a key step the stereospecific photochemical ring expansion of a cyclobutanone.
