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N2001

Sigma-Aldrich

Neostigmine bromide

≥98% (HPLC and titration), powder

Synonym(s):

3-(N,N-Dimethylcarbamoyloxy)-N,N,N,-trimethylanilinium bromide, Prostigmine

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About This Item

Empirical Formula (Hill Notation):
C12H19BrN2O2
CAS Number:
114-80-7
Molecular Weight:
303.20
EC Number:
204-054-8
MDL number:
MFCD00011795
UNSPSC Code:
12352200
PubChem Substance ID:
24277854
NACRES:
NA.77

Assay

≥98% (HPLC and titration)

form

powder

color

white

mp

175-177 °C (lit.)

solubility

H2O: 1 g/mL
ethanol: soluble

SMILES string

[Br-].CN(C)C(=O)Oc1cccc(c1)[N+](C)(C)C

InChI

1S/C12H19N2O2.BrH/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;/h6-9H,1-5H3;1H/q+1;/p-1

InChI key

LULNWZDBKTWDGK-UHFFFAOYSA-M

Gene Information

human ... ACHE(43)

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Application

Neostigmine bromide has been used as an acetyl cholinesterase (AChE) inhibitor:
  • to control reaction specificity of acetylcholinesterase in coronal organ of Botryllus schlosseri.
  • to study its effects on abnormal contraction of pyloric circular smooth muscle strips (PCSMS).
  • to study its effects on depolarization of bag cell neurons.

Biochem/physiol Actions

Neostigmine bromide is a quaternary amine. It is involved in elongating and boosting the muscarinic and nicotinic effects of acetylcholine by inhibiting cholinesterase activity. It is used in anesthesia to reverse the neuromuscular blockade produced by competitive neuromuscular blockers.
Reversible inhibitor of acetylcholinesterase that is similar to eserine, but does not cross the blood-brain barrier.

Features and Benefits

This compound is featured on the Acetylcholine Synthesis and Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lucia Manni et al.
Integrative and comparative biology, 58(2), 317-328 (2018-06-07)
Tunicates, the sister group of vertebrates, possess a mechanoreceptor organ, the coronal organ, which is considered the best candidate to address the controversial issue of vertebrate hair cell evolution. The organ, located at the base of the oral siphon, controls
Effect of aurantii fructus immaturus flavonoid on the contraction of isolated gastric smooth muscle strips in rats
Wu Z, et al.
Evidence-Based Complementary and Alternative Medicine : ECAM, 2016(2), 317-328 (2016)
Modified carbon paste sensor for the potentiometric determination of neostigmine bromide in pharmaceutical formulations, human plasma and urine
Khorshid, A F and Issa, Y M
Biosensors And Bioelectronics, 51, 143-149 (2014)
Zhenyu Wu et al.
Evidence-based complementary and alternative medicine : eCAM, 2016, 5616905-5616905 (2016-07-19)
This study was designed to investigate the effect of Aurantii fructus immaturus flavonoid (AFIF) on the contraction of isolated gastric smooth muscle in rats and explore its underlying mechanisms. Isolated antral longitudinal smooth muscle strip (ALSMS) and pyloric circular smooth
M Weinstock et al.
The Journal of pharmacology and experimental therapeutics, 218(2), 504-508 (1981-08-01)
The influence of physostigmine was studied on the effect of morphine on the cardiovascular and respiratory systems in conscious rabbits. Morphine (4 mg/kg i.v.) caused analgesia, bradycardia, hypotension and respiratory depression, as indicated by a fall in respiratory rate of
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