Arecoline hydrobromide appears as a white crystalline powder or solid, and its pure white color makes it easy to identify in the laboratory and pharmaceutical fields. This powdered substance is odorless under normal circumstances, but has a bitter taste and certain toxicity. It deteriorates when exposed to light. Melting point 170-171 ° C. Has excellent solubility in water and ethanol. This good solubility allows for easy mixing with solvents when preparing drugs and conducting chemical research, which is beneficial for its use in various application scenarios. Anti intestinal worm drugs are mostly used for veterinary treatment. It has a strong paralyzing effect on the muscles of tapeworms and can also enhance the host's intestinal peristalsis, thus producing a expelling effect on tapeworms. Mainly used to treat common tapeworm diseases in dogs and poultry.
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Chemical Formula |
C8H13NO2 |
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Exact Mass |
155 |
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Molecular Weight |
155 |
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m/z |
155 (100.0%), 156 (8.7%) |
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Elemental Analysis |
C, 61.91; H, 8.44; N, 9.03; O, 20.62 |
As a common chemical substance, there are various methods for synthesizing arecoline hydrobromide. Once again, I will list the following three for reference only.
Method 1:
The synthesis of product usually involves the reaction between arecoline and hydrobromic acid. As a derivative of arecoline, bromoaarecoline contains bromine atoms in its structure. In theory, bromoaarecoline can react with sodium hydroxide (NaOH) to form a sodium salt of arecoline, which then reacts with hydrobromic acid (HBr) to ultimately form hydrobromoaarecoline. But this process needs to be carried out in two steps, because bromoaarecoline reacts directly with sodium hydroxide and does not directly generate hydrobromoaarecoline.
Detailed steps and chemical equations
In this step, bromoaarecoline (assumed to have a structural formula of C9H10NO2Br, but for simplicity, we neglected the specific substitution positions and quantities) reacts with sodium hydroxide to generate sodium salts and water of arecoline.
Chemical equation:
C9H10NO2Br+NaOH → C9H10NO2Na+H2O+Br ⁻
In this step, the bromine atom of bromoaarecoline is replaced by a hydroxide ion (OH ⁻), forming the sodium salt (C9H10NO2Na) and bromine ion (Br ⁻) of arecoline.
In the second step, the sodium salt of arecoline reacts with hydrobromic acid to produce hydrobromic arecoline (C9H13NO2 · HBr) and water.
Chemical equation:
C9H10NO2Na+HBr → C9H13NO2 · HBr+NaBr
In this step, the sodium salt of arecoline undergoes acid-base neutralization reaction with hydrobromic acid, producing and sodium bromide (NaBr).
Method 2:
Arecoline is an alkaloid found in betel nut, which contains a nitrogen atom in its chemical structure and can accept hydrogen ions (H+), exhibiting alkalinity. Hydrobromic acid (HBr) is a strong acid that can release hydrogen ions. When arecoline meets hydrobromic acid, the nitrogen atom in arecoline will combine with the hydrogen ion in hydrobromic acid to form the hydrobromate of arecoline, which is it.
Arecoline+HBr → C8H14BrNO2
Detailed steps
1. Preparation of raw materials:
Firstly, a certain amount of arecoline and hydrobromic acid needs to be prepared. Both substances need to be mixed in a certain proportion to ensure complete reaction.
2. Mixing ingredients:
Mix arecoline and hydrobromic acid in an appropriate container. To ensure a uniform reaction, stirring or shaking the container can be used.
3. Observation reaction:
During the mixing process, it can be observed that arecoline gradually dissolves in hydrobromic acid, forming a homogeneous reaction system. Meanwhile, due to the strong acidity of hydrobromic acid, a certain amount of heat may be generated during the reaction process.
4. Separation of products:
After the reaction is completed, the products need to be separated. Due to its high solubility in water, it can be separated from the reaction system through methods such as filtration or evaporative crystallization.
5. Purified product:
The separated it may contain some impurities, such as unreacted arecoline, hydrobromic acid, etc. In order to obtain high purity product, purification methods such as recrystallization and washing can be used.
Method 3:
The reaction between arecoline and phosphorus tribromide to generate hydrobromate arecoline is not a direct or conventional reaction pathway. Usually, arecoline hydrobromide is obtained by directly reacting arecoline with hydrobromic acid. However, if phosphorus tribromide (PBr3) is used to prepare product, it may involve a series of chemical reactions, including bromination and subsequent acidification steps.
Detailed steps and chemical equations
The reaction between arecoline and phosphorus tribromide (PBr3) may generate brominated arecoline. This step is an electrophilic substitution reaction, where the bromine atom in phosphorus tribromide replaces a hydrogen atom in the betel nut alkaloid molecule.
Arecoline+PBr3 → Brominated Arecoline+PH3
This reaction needs to be carried out under anhydrous conditions, as phosphorus tribromide reacts violently with water. The control of reaction temperature and time is crucial for the selectivity and yield of the product.
Brominated arecoline may then undergo a hydrolysis step, replacing the bromine atom with a hydroxyl group (OH), and then undergo an acidification step to generate hydrobromate arecoline.
Brominated Arecoline+H2O → Hydroxylated Arecoline+HBr
The acidification step involves reacting the generated hydroxyarecoline with hydrobromic acid to produce hydrobromic arecoline:
Hydrolated Arecoline+HBr → C8H14BrNO2+H2O
These two steps may need to be carried out under different reaction conditions, for example, hydrolysis may need to be carried out in an alkaline environment, while acidification needs to be carried out in an acidic environment.
In summary, although the pathway for preparing hydrobromic acid arecoline by reacting arecoline with phosphorus tribromide is theoretically feasible, careful handling of various chemical reaction conditions is necessary in practical operation to ensure safety and product purity. In addition, this method is not a conventional method for preparing product, so it is not recommended to use it in the laboratory or industrial production without sufficient experimental verification.
Classification of arecoline hydrobromide:
1. National biological reference standards refer to biological reagents, biomaterials, or specific antiserum calibrated with international reference standards or independently developed by China (without international reference standards) for qualitative identification or disease diagnosis of microorganisms (or their products); Or refers to a reference substance used for quantitative detection of the biological potency of certain products, such as a reference substance used for the determination of measles live vaccine titers or toxoid flocculent units, whose potency is expressed in specific active units and not in (IU).
2. National biological standards refer to standard substances calibrated with international standards or independently developed by China (where there is no international biological standard) for quantitative determination of the potency or toxicity of a product. Their biological activity is expressed in International Units (IU) or Units (U).
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