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Neostigmine bromide

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Identification
Molecular formula
C12H19BrN2O2
CAS number
114-80-7
IUPAC name
[3-(dimethylcarbamoyloxy)phenyl]-trimethyl-ammonium;bromide
State
State

At room temperature, neostigmine bromide is typically in a solid state. Its crystalline powder form maintains its stability under standard conditions, facilitating its use in pharmacological preparations.

Melting point (Celsius)
158.00
Melting point (Kelvin)
431.15
Boiling point (Celsius)
235.00
Boiling point (Kelvin)
508.15
General information
Molecular weight
303.20g/mol
Molar mass
303.2220g/mol
Density
1.5150g/cm3
Appearence

Neostigmine bromide appears as a white to off-white crystalline powder. It is odorless and is known for its hygroscopic nature, meaning it can absorb moisture from the environment which sometimes causes clumping. It is soluble in water, making it favorable for medicinal applications.

Comment on solubility

Solubility of [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-ammonium bromide

[3-(dimethylcarbamoyloxy)phenyl]-trimethyl-ammonium bromide, often referred to as a quaternary ammonium compound, exhibits interesting solubility characteristics that are worth noting.

General Solubility Properties

This compound is known to be soluble in a variety of solvents due to its ionic nature:

  • Water: It is generally soluble in aqueous solutions owing to the presence of the bromide anion and the positively charged ammonium group.
  • Polar organic solvents: Solvents such as methanol and ethanol can also dissolve this compound effectively.
  • Low solubility in non-polar solvents: Compounds of this type typically show low solubility in non-polar solvents like hexane or toluene.

Factors Influencing Solubility

The solubility of [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-ammonium bromide can be influenced by several factors:

  • Temperature: Increasing the temperature usually enhances solubility for ionic compounds.
  • pH Levels: Variation in pH can sometimes alter the solubility due to changes in charge and ionization state.
  • Concentration: The solubility limits may vary based on the concentration of the compound and the solvent used.

In summary, understanding the solubility of [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-ammonium bromide is essential for applications in various fields, particularly in pharmaceutical formulations and chemical synthesis, where solubility can significantly impact efficacy and interactions. This compound is predominantly soluble in water and polar solvents, making it a versatile component in solution-based applications.

Interesting facts

Interesting Facts about [3-(Dimethylcarbamoyloxy)phenyl]-trimethyl-ammonium Bromide

[3-(Dimethylcarbamoyloxy)phenyl]-trimethyl-ammonium bromide, often referred to in the scientific community as a quaternary ammonium compound, is a fascinating subject of study for several reasons:

  • Quaternary Ammonium Compounds: This compound is part of a larger family known for their antimicrobial properties and effectiveness as surfactants. These compounds are widely used in disinfectants, personal care products, and even in agriculture.
  • Biological Applications: The presence of the dimethylcarbamoyloxy group lends this compound intriguing biological properties. Research indicates that compounds with similar structures have potential applications in drug delivery systems, expanding their utility in medicinal chemistry.
  • Surface Activity: Due to its amphiphilic nature, it exhibits surface-active properties which can enhance the efficacy of formulations in various industries, particularly in cleaning agents and emulsifiers.
  • Interaction with Biological Systems: The trimethylammonium group contributes to its cationic nature, allowing it to interact with negatively charged cellular components like membranes, proteins, and nucleic acids. This property makes it a valuable tool in biochemical experiments.
  • Reactivity and Stability: The bromide ion in this compound plays a significant role in its stability and reactivity. Ammonium bromides are known for their low toxicity and chemical stability, making this compound a safer alternative in laboratory usage compared to halides with other counterions.

In summary, [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-ammonium bromide is not just an ordinary compound; it serves as a cornerstone for numerous scientific ventures, particularly in medicinal chemistry and biochemistry. Its complexity and versatility open avenues for further research and innovative applications in various fields.

Synonyms
neostigmine bromide
114-80-7
Vagostigmin
Kirkstigmine bromide
Eustigmin bromide
Neoserine bromide
Syntostigmin bromide
Neostigmini bromidum
3-((Dimethylcarbamoyl)oxy)-N,N,N-trimethylbenzenaminium bromide
Neo proserine
neo-Proserin
Proserine bromide
Stigmanol bromide
Synstigmin bromide
Leostigmine bromide
Philostigmin bromide
Prostigmin
Neoproserine
Bromure de neostigmine
Bromuro de neostigmina
Neostigmine methyl bromide
Neostigmine (Bromide)
3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium bromide
Vagostigmin (TN)
(m-Hydroxyphenyl)trimethylammonium bromide dimethylcarbamate
NSC-757233
DTXSID9041075
CHEBI:179557
005SYP50G5
MFCD00011795
3-Dimethylcarbamoxyphenyl trimethyl ammonium bromide
NEO PROSERINE [JAN]
114-80-7 (bromide)
MLS000028387
[3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium;bromide
DTXCID7021075
NEOSTIGMINE BROMIDE [MI]
3-Hydroxyphenyltrimethylammonium bromide dimethylcarbamic ester
NEOSTIGMINE BROMIDE [INN]
NEOSTIGMINE BROMIDE [JAN]
NEOSTIGMINE BROMIDE [VANDF]
NEOSTIGMINE BROMIDE [MART.]
NEOSTIGMINE BROMIDE [USP-RS]
NEOSTIGMINE BROMIDE [WHO-DD]
NEOSTIGMINE BROMIDE [WHO-IP]
Neo proserine (JAN)
SMR000058591
NEOSTIGMINE BROMIDE [EP MONOGRAPH]
NEOSTIGMINE BROMIDE [USP MONOGRAPH]
NEOSTIGMINI BROMIDUM [WHO-IP LATIN]
Stigmosan bromide
Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-, bromide
Prostigmin bromide
Prostigmine bromide
Synstigmini bromidum
Vagostigmine bromide
Syntostigmine bromide
3-(Dimethylcarbamoyloxy)trimethylanilinium ion Bromatum
Synthostigmine bromide
Syntostigmin (tablet)
Synstigminbromid
NEOSTIGMINE BROMIDE (MART.)
NEOSTIGMINE BROMIDE (USP-RS)
Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-, bromide
Neostigmina bromuro
Neostigmina bromuro [DCIT]
NEOSTIGMINE BROMIDE (EP MONOGRAPH)
NEOSTIGMINE BROMIDE (USP MONOGRAPH)
Neostigmini bromidum [INN-Latin]
NEOSTIGMINEBROMIDE
SR-01000000073
NCGC00163240-01
CAS-114-80-7
EINECS 204-054-8
Bromure de neostigmine [INN-French]
Bromuro de neostigmina [INN-Spanish]
(3-(dimethylcarbamoyloxy)phenyl)-trimethylazanium;bromide
3-((dimethylcarbamoyl)oxy)-N,N,N-trimethylanilinium bromide
UNII-005SYP50G5
Eustigmin bromide;Neoserine bromide
Prestwick_352
Neostigmine bromide [USP:INN:BAN:JAN]
Opera_ID_1504
Carbamic acid, dimethyl-, ester with (m-hydroxyphenyl)trimethylammonium bromide
SCHEMBL41128
MLS001146913
CHEMBL54126
SPECTRUM1500428
LCZC2572
Neostigmine bromide (Prostigmin)
HMS500I07
HY-B0423R
Juvastigmin;Neoesserin;Neostigmin
LULNWZDBKTWDGK-UHFFFAOYSA-M
Neostigmine (Bromide) (Standard)
HMS1569M18
HMS1920P15
HMS2091H18
HMS2096M18
HMS2235J11
HMS3262D13
HMS3372E02
HMS3713M18
Pharmakon1600-01500428
HY-B0423
Neostigmine bromide (JAN/USP/INN)
Tox21_112037
Tox21_500816
CCG-39110
NSC757233
s2490
AKOS015895725
AMMONIUM, (m-HYDROXYPHENYL)TRIMETHYL-, BROMIDE, DIMETHYLCARBAMATE
Tox21_112037_1
FN26183
LP00816
NSC 757233
NCGC00015730-11
NCGC00094149-01
NCGC00094149-02
NCGC00094149-03
NCGC00094149-04
NCGC00261501-01
BS-14646
DA-66031
MLS-0002855.P042
EU-0100816
N0358
NS00079222
C08197
C71473
D00995
N 2001
A803245
EN300-12576352
SR-01000000073-3
SR-01000000073-5
SR-01000000073-7
(3-Dimethylcarbamoyloxyphenyl)trimethylammonium Bromide
Q27105147
Neostigmine bromide, >=98% (HPLC and titration), powder
(3-Hydroxyphenyl)trimethylammonium Bromide Dimethyl Carbamate
[3-[dimethylamino(oxo)methoxy]phenyl]-trimethylammonium bromide
3-(N,N-Dimethylcarbamoyloxy)-N,N,N,-trimethylanilinium bromide
Neostigmine bromide, European Pharmacopoeia (EP) Reference Standard
Neostigmine bromide, United States Pharmacopeia (USP) Reference Standard
204-054-8