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Structural formula
Structural formula of the neostigmine cation
Neostigmine cation [anion (bromide or methyl sulfate) is not shown]
Surname Neostigmine
other names

3- (dimethylcarbamoyloxy) - N , N , N -trimethylbenzenaminium

Molecular formula C 12 H 19 N 2 O 2 +
Brief description

white solid (bromide)

External identifiers / databases
CAS number
  • 59-99-4
  • 114-80-7 (bromide)
  • 51-60-5 (methyl sulfate)
ECHA InfoCard 100,305,602
PubChem 4456
ChemSpider 4301
DrugBank DB01400
Wikidata Q410546
Drug information
ATC code

N07 AA01 , S01 EB06

Drug class


Mechanism of action

Acetylcholinesterase - inhibitory

Molar mass 223.29 g · mol -1
Physical state


Melting point

175–177 ° C (bromide)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic 08 - Dangerous to health


H and P phrases H: 300-310-315-317-319-330-334-335
P: 260-264-280-284-302 + 350-305 + 351 + 338
Toxicological data

12.34 mg kg −1 ( LD 50mouseoral )

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.

In combination with pilocarpine , neostigmine bromide is used in eye drops to treat glaucoma .


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 .

Pharmaceutical data

Neostigmine is given intravenously. The water-soluble salts neostigmine bromide and neostigmine metal sulphate are used medicinally.

Trade names


Prostigmine (CH) as well as generics (D), normastigmine (A)

Web links

  • Entry to neostigmine at Vetpharm, accessed on August 5 2012th

Individual evidence

  1. a b c d Datasheet Neostigmine bromide from Sigma-Aldrich , accessed on April 15, 2011 ( PDF ).
  2. 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 .
  3. 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 .
  4. ^ Entry on neostigmine in the ChemIDplus database of the United States National Library of Medicine (NLM) .