Neostigmine bromide Chemical Properties

Melting point:

175-177 °C(lit.)

Density 

1.4344 (rough estimate)

refractive index 

1.5410 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

H₂O: 1 g/mL

form 

powder

color 

white

PH

5.2～6.2 (100g/l, 25℃)

Water Solubility 

1 g/ mL

Merck 

14,6464

BCS Class

3

EPA Substance Registry System

Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-, bromide (114-80-7)

Safety Information

Hazard Codes 

T+,T

Risk Statements 

26/27/28-36/37/38-42/43-25

Safety Statements 

22-26-36/37/39-45-37/39-28A

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

BR3150000

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29239000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Neostigmine bromide Usage And Synthesis

Chemical Properties

Crystalline Solid

Uses

antiscorbutic, antiviral

Uses

Cholinergic; miotic; antidote (curare)

Uses

A reversible acetylcholinesterase inhibitor

Uses

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.

Definition

ChEBI: Neostigmine bromide is the bromide salt of neostigmine. It contains a neostigmine.

General Description

Neostigmine bromide, (m-hydroxyphenyl)trimethylammonium bromide dimethylcarbamateor the dimethylcarbamic ester of 3-hydroxyphenyltrimethylammoniumbromide (Prostigmin bromide), is usedas an antidote to nondepolarizing neuromuscular blockingdrugs and in the treatment of myasthenia gravis. It occurs asa bitter, odorless, white, crystalline powder. It is soluble inwater and alcohol. The crystals are much less hygroscopicthan those of neostigmine methylsulfate and thus may beused in tablets. Solutions are stable and may be sterilized byboiling. Aqueous solutions are neutral to litmus.

Biological Activity

neostigmine bromide is a reversible inhibitor of acetylcholinesterase.[1]ache (acetylcholinesterase) is a hydrolase that hydrolyzes the neurotransmitter acetylcholine at the neuromuscular junction and cholinergic synaspe. it terminates the signal transductions and plays a role in neuronal apoptosis.neostigmine bromide is a quaternary amine that blocked cholinesterase activity to extend and enhance the muscarinic and nicotinic effects of acetylcholine. it is implicated for the treatment of primary open-angle glaucoma, postoperative urinary retention, paralytic ileus, myasthenia gravis etc. it is also reported to be an adjuvant to local anaesthetics and opioids for post-surgical pain after gynaecological or abdominal surgery. [1]

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.

Clinical Use

Use of physostigmine, as a prototype of an indirect-actingparasympathomimetic drug, facilitated the development ofstigmine, in which a trimethylamine group was placed para toa dimethylcarbamate group in benzene. Better inhibition ofcholinesterase was observed when these groups were placedmeta to each other as in neostigmine, a more active and usefulagent. Although physostigmine contains a methylcarbamatefunctional group, greater chemical stability towardhydrolysis was obtained with the dimethylcarbamyl group inneostigmine.

Safety Profile

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. When heated to decomposition it emits very toxic fumes of Br-, NH3, and NOx. See also CARBAMATES and BROMIDES.

Purification Methods

Crystallise neostigmine bromide from EtOH/diethyl ether. Its solubility in H2O is ~50%. [Beilstein 13 III 939.] (It is cholinergic and highly TOXIC.) The starting material 3-dimethylcarbamoyl-N,N-dimethylaniline [59-99-4] has b 195o/20mm [Beilstein 13 III 936], and its picrate has m 138o (from EtOH).

References

[1] el-kosasy am, nebsen m, abd el-rahman mk, salem my, el-bardicy mg. comparative study of 2-hydroxy propyl beta cyclodextrin and calixarene as ionophores in potentiometric ion-selective electrodes for neostigmine bromide. talanta. 2011 aug 15;85(2):913-8.

Neostigmine bromide (114-80-7)Related Product Information

• Ammonium sulfate
• Ethidium bromide
• 4-Dimethylaminobenzoic acid
• Dimidium bromide
• 4-Dimethylaminobenzaldehyde
• Dimethyldimethoxysilane
• Ammonium acetate
• 4-Dimethylaminopyridine
• Trimethyl borate
• Ammonium hydroxide
• 1,1-Dimethoxyethane
• Rocuronium bromide
• Vecuronium bromide
• Allyl bromide
• Sodium bromate
• Ammonium chloride
• Molybdic acid
• Neostigmine Impurity 1