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CAS 59-99-4

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Neostigmine

Description:
Neostigmine is a synthetic chemical compound classified as a reversible inhibitor of the enzyme acetylcholinesterase. It is primarily used in the treatment of myasthenia gravis, a neuromuscular disorder characterized by weakness and rapid fatigue of voluntary muscles. Neostigmine enhances the action of acetylcholine at neuromuscular junctions by preventing its breakdown, thereby improving muscle contraction. The compound is typically administered in its bromide salt form and is known for its relatively short duration of action compared to other acetylcholinesterase inhibitors. Neostigmine is a quaternary ammonium compound, which limits its ability to cross the blood-brain barrier, resulting in peripheral rather than central nervous system effects. Common side effects may include gastrointestinal disturbances, increased salivation, and muscle cramps. Due to its pharmacological properties, neostigmine is also utilized in certain surgical settings to reverse the effects of neuromuscular blocking agents. Its chemical structure features a carbamate group, which is essential for its mechanism of action.
Formula:C12H19N2O2
InChI:InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1
InChI key:InChIKey=ALWKGYPQUAPLQC-UHFFFAOYSA-N
SMILES:O(C(N(C)C)=O)C1=CC([N+](C)(C)C)=CC=C1
Synonyms:
  • 3-Dimethylcarbamoxyphenyltrimethylammonium salt
  • 3-Trimethylammoniumphenyl N,N-dimethylcarbamate
  • 3-[(Dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium
  • 3-[[(Dimethylamino)carbonyl]oxy]-N,N,N-trimethylbenzenaminium
  • Ammonium, (m-hydroxyphenyl)trimethyl-, dimethylcarbamate (ester)
  • Benzeneaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-
  • Eustigmin
  • Eustigmine
  • Neostigmine
  • Prostigmin
  • See more synonyms
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