|Neostigmine cation [anion (bromide or methyl sulfate) is not shown]|
3- (dimethylcarbamoyloxy) - N , N , N -trimethylbenzenaminium
|Molecular formula||C 12 H 19 N 2 O 2 +|
white solid (bromide)
|External identifiers / databases|
|Mechanism of action|
|Molar mass||223.29 g · mol -1|
175–177 ° C (bromide)
|As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .|
Neostigmine inhibits the enzyme acetylcholinesterase . This enzyme splits the chemical transmitter acetylcholine both at various cholinergic synapses (muscarinic, nicotinic) and neuromuscular endplates. Thus, after being released into the synaptic gap, it is inactivated and its effect is limited. When the enzyme is inhibited by substances like neostigmine, the concentration of acetylcholine in the synaptic cleft increases rapidly. This z. B. stimulates the parasympathetic nervous system and causes an increase in tone in the skeletal muscles . Physostigmine , the insecticide E605 or some chemical warfare agents (e.g. soman ) have a similar effect .
Neostigmine is in cases of poisoning with competitive acetylcholine receptor - antagonists (eg. Curare applied). It is also used in the antagonization of non-depolarizing muscle relaxants, for example in the diversion of anesthesia . To avoid undesirable (side) effects that are mediated by muscarinic acetylcholine receptors and which lead to an increase in the parasympathetic tone ( bradycardia , bronchoconstriction, etc.), atropine is also administered, which blocks the muscarinic acetylcholine receptors, but the nicotinic acetylcholine receptors (an motor end plate ) not occupied.
For myasthenia , neostigmine can be used to counteract muscle weakness. In the presence of an isolated paralytic ileus , neostigmine can be used to stimulate the motility and peristalsis of the intestine again.
As a quaternary ammonium compound , neostigmine is poorly absorbed from the gastrointestinal tract and - in contrast to the tertiary amine physostigmine - does not cross the blood-brain barrier , i.e. it is not accessible to the CNS .
Prostigmine (CH) as well as generics (D), normastigmine (A)
- Entry to neostigmine at Vetpharm, accessed on August 5 2012th
- Datasheet Neostigmine bromide from Sigma-Aldrich , accessed on April 15, 2011 ( PDF ).
- External identifiers or database links for neostigmine bromide : CAS number: 114-80-7, EC number: 204-054-8, ECHA InfoCard: 100.003.686 , PubChem : 8246 , ChemSpider : 7950 , Wikidata : Q27105147 .
- External identifiers or database links for neostigmine methyl sulfate : CAS number: 51-60-5, EC number: 200-109-5, ECHA InfoCard: 100.000.100 , PubChem : 5824 , ChemSpider : 5619 , Wikidata : Q98093892 .
- Entry on neostigmine in the ChemIDplus database of the United States National Library of Medicine (NLM) .