2936-25-6 Usage
Uses
Used in Pharmaceutical Research:
(+/-)-MUSCARINE CHLORIDE is used as a research compound for studying the effects and mechanisms of muscarinic acetylcholine receptors. Its ability to mimic acetylcholine's action on peripheral autonomic effector organs aids in understanding the role of these receptors in various physiological processes.
Used in Toxicological Studies:
(+/-)-MUSCARINE CHLORIDE is used as a toxicological agent to investigate the effects of muscarinic receptor agonists on the human body. This helps in developing antidotes and understanding the potential risks associated with exposure to such substances.
Used in Drug Development:
(+/-)-MUSCARINE CHLORIDE is used as a lead compound in the development of new drugs targeting muscarinic acetylcholine receptors. Its interaction with these receptors can provide insights into the design of more effective and safer drugs for treating various conditions.
Used in Educational Purposes:
(+/-)-MUSCARINE CHLORIDE is used as an educational tool in teaching pharmacology, toxicology, and related fields. It helps students understand the concepts of receptor agonists, antagonists, and the role of acetylcholine in the nervous system.
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 academic research and scientific papers
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.
Chelation-Controlled Synthesis of (+/-)-Muscarine
Still, W.Clark,Schneider, Josef A.
, p. 3375 - 3376 (2007/10/02)
The chelation controlled addition of Grignard reagents to chiral α-alkoxy aldehydes to give threo diol derivatives is synthetically useful in highly oxygenated systems and is used here as the key step in a novel synthesis of (+/-)-muscarine from cyclopentadiene.
