Malcolm Rivera
Methocarbamol is a drug used to treat muscle spasms and pain caused by muscle injuries. It is also known as a muscle relaxant. The methocarbamol beta isomer is one of the drug's critical impurities and is essential for its commercial production. The isomer is prepared through a five-step reaction using 2-((methoxyphenoxy)methyl)ethylene oxide as a starting raw material. This isomer is highly characterised and complies with stringent regulatory standards, making it suitable for various analytical applications.
| Characteristics | Values |
|---|---|
| Synonyms | Methocarbamol B-Isomer, 1-Descarbamoyl-2-carbamoyl Methocarbamol, 3-(2-Methoxyphenoxy)-1, 2-propanediol 2-Carbamate |
| Chemical Name | (±) -3- [o- methoxy phenoxy] -1,3-PD -1- carbamate |
| Raw Material | 2-((Methoxyphenoxy)methyl)ethylene oxide compound 1 |
| Raw Material | 2-((Methoxy phenoxy) methyl) oxirane |
| Purity | 99.6% to 99.7% |
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What You'll Learn
- Methocarbamol B-Isomer is a highly characterised reference material
- It is essential for use in commercial production of Methocarbamol
- The Methocarbamol beta isomer is a medicinal chemistry art
- It is used for impurity quantification during methocarbamol production
- The beta isomer has a chemical name of (±) -3- [o- methoxy phenoxy] -1,3-PD -1- carbamate
Methocarbamol B-Isomer is a highly characterised reference material
Methocarbamol B-Isomer, also known as 1-Descarbamoyl-2-carbamoyl Methocarbamol or 3-(2-Methoxyphenoxy)-1, 2-propanediol 2-Carbamate, is a highly characterised reference material. It is a muscle relaxant medication used in the short term with physical therapy and other treatments to alleviate painful symptoms caused by muscle strains and spasms. It is also used to control the neuromuscular spasms of tetanus.
Methocarbamol was developed in the early 1950s and approved for medical use in the United States in 1957. It is available as a generic medication and is often prescribed, with more than 5 million prescriptions in 2022. The medication is available in tablet and intramuscular injection form. In the US, it is a prescription medicine, while in Canada, it is sold over the counter at a lower dose.
The mechanism of action of methocarbamol is thought to be dependent on its central nervous system depressant activity. It may mediate through blocking spinal polysynaptic reflexes, decreasing nerve transmission in spinal and supraspinal polysynaptic pathways, and prolonging the refractory period of muscle cells. It has no effect on the contraction of muscle fibres, motor end plates, or nerve fibres.
Methocarbamol has significant potential adverse effects, especially on the central nervous system. These may include drowsiness, blurred vision, headache, nausea, skin rash, upset stomach, flushing, mood changes, trouble urinating, itchiness, fever, and changes in heart rate. It may also cause respiratory depression when combined with certain other medications.
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It is essential for use in commercial production of Methocarbamol
The β-isomer of methocarbamol is a highly characterised reference material that is essential for use in the commercial production of methocarbamol. It is a central nervous system (CNS) depressant used in the treatment of skeletal muscle spasms. During the synthesis of methocarbamol from guaifenesin, an unknown impurity was observed. This unknown impurity was later designated as the β-isomer of methocarbamol. The presence of impurities in active pharmaceutical ingredients (APIs) and formulations can degrade therapeutic efficacy, cause unwanted side effects, and affect stability. Therefore, it is crucial to identify, isolate, and purify these impurities to ensure the safety and quality of the final product.
The β-isomer of methocarbamol, also known as Methocarbamol B-Isomer or 1-Descarbamoyl-2-carbamoyl Methocarbamol, is one such impurity that has been identified and characterised. It is produced as a potential process-related impurity during the amination of guaifenesin using phosgene in ethanol. The β-isomer has been consistently observed in high-performance liquid chromatography (HPLC) analysis, along with the final product and starting materials.
To ensure the safety and efficacy of methocarbamol, it is essential to address the presence of the β-isomer impurity. This involves understanding its formation, identification, isolation, and characterisation. The β-isomer of methocarbamol has been the subject of studies that aim to purify the impurity and characterise it using nuclear magnetic resonance (NMR) and mass spectrometry. These characterisation techniques provide valuable insights into the structure and properties of the impurity.
Additionally, the β-isomer of methocarbamol complies with stringent regulatory standards set by organisations such as the United States Pharmacopoeia (USP), European Medicines Agency (EMA), Japanese Pharmacopoeia (JP), and British Pharmacopoeia (BP). This compliance ensures its accuracy and reliability for a wide range of analytical applications. The detailed Structure Elucidation Report (SER) provided with the β-isomer further enhances its reliability and makes it a crucial reference material for commercial methocarbamol production.
The Methocarbamol beta isomer is a medicinal chemistry art
Methocarbamol is a muscle relaxant used to treat acute, painful musculoskeletal spasms. It is a guaiacol glyceryl ether and a CNS depressant indicated for use alongside rest, physical therapy, and other treatments to control the discomfort associated with various acute musculoskeletal conditions. It was developed in the early 1950s and approved for medical use in the United States in 1957.
The Methocarbamol beta isomer is a well-characterized reference material that complies with stringent regulatory standards set by organizations such as USP, EMA, JP, and BP. It is used in the correlational study of Methocarbamol impurities, providing valuable insights into the quantification and analysis of impurities during the production of Methocarbamol. This helps to ensure the safety and effectiveness of the medication for patients.
The preparation of the Methocarbamol beta isomer involves specific chemical processes. In one method, the raw material undergoes chlorination, esterification, amidation, acetylation, and acid digestion degreasing reactions to obtain the target product. Another preparation method involves mixing compound 5, methanol, and p-methyl benzenesulfonic acid, followed by stirring, concentrating, and adding water and toluene at specific temperatures. These processes allow for the efficient preparation of the highly purified Methocarbamol beta isomer, contributing to the advancement of medicinal chemistry and the development of safer and more effective treatments.
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It is used for impurity quantification during methocarbamol production
Methocarbamol is a medication used for short-term musculoskeletal pain. It is a centrally acting skeletal muscle relaxant with adverse effects, especially on the central nervous system. It is also known by its brand name Robaxin. It was developed in the 1950s and approved for medical use in the United States in 1957.
The methocarbamol isomer, also known as the Methocarbamol B-Isomer, is a highly characterised reference material. It is essential for use in commercial methocarbamol production. The isomer is used for impurity quantification during methocarbamol production to ensure the accuracy and reliability of the product.
Impurities in drugs can be identified and quantified through various methods, such as NMR, MS data analysis, and EPR spectroscopy. Impurities can also be identified through X-ray fluorescence (XRF), which can detect heavy metal impurities such as As, Hg, Co, and Ni. These techniques help ensure the safety and efficacy of the drug product.
The methocarbamol isomer, or B-Isomer, plays a crucial role in ensuring the quality and purity of the final methocarbamol product. By using these analytical techniques, any impurities can be identified, quantified, and monitored during the production process, ensuring that the methocarbamol medication meets regulatory standards and is safe for patient use.
Overall, the methocarbamol isomer is an important tool in the commercial production of methocarbamol, helping to maintain the accuracy, reliability, and safety of the medication.
The beta isomer has a chemical name of (±) -3- [o- methoxy phenoxy] -1,3-PD -1- carbamate
Methocarbamol is a drug used to treat muscle spasms and pain. It is a white, odourless crystalline powder that is slightly soluble in water and has a molecular weight of about 215.23 g/mol. The chemical formula for methocarbamol is C11H15NO5, and it has a chemical name of 3-(2-methoxyphenoxy)-1,2-propanediol 2-carbamate.
The beta isomer of methocarbamol has the chemical name (±) -3- [o-methoxy phenoxy] -1,3-PD -1- carbamate. This isomer is also known as Methocarbamol B-Isomer, 1-Descarbamoyl-2-carbamoyl Methocarbamol, or 3-(2-Methoxyphenoxy)-1, 2-propanediol 2-Carbamate. It is a highly characterised reference material that complies with regulatory standards set by USP, EMA, JP, and BP. This isomer is essential for use in Abbreviated New Drug Applications (ANDA), New Drug Applications (NDA), and the commercial production of Methocarbamol.
The structure of methocarbamol and its isomers can be complex, and it is important to have accurate knowledge about its composition for various applications. The beta isomer, in particular, is a well-studied reference material with a detailed Structure Elucidation Report (SER) that ensures its accuracy and reliability for a wide range of analytical uses.
The applications of methocarbamol isomers, including the beta isomer, are diverse and important in the field of medicine and chemistry. The beta isomer's regulatory compliance and characterisation make it a valuable substance for drug development and commercial production. Its unique structural and chemical properties contribute to its utility in various analytical procedures and synthetic processes.
In conclusion, the beta isomer of methocarbamol, with the chemical name (±) -3- [o-methoxy phenoxy] -1,3-PD -1- carbamate, is a significant variant of the drug methocarbamol. Its characterisation, regulatory compliance, and utility in drug applications and commercial production highlight its importance in the field of medicine and chemistry.
Frequently asked questions
1-Hydroxy-3-(2-methoxyphenoxy)propan-2-yl carbamate, also known as the β-isomer, is a degradation product of methocarbamol.
An isomer is a compound with the same chemical formula as another compound but with a different structural arrangement of atoms.
The β-isomer impurity is generated during the compounding process due to the addition of methocarbamol before the buffer.
The β-isomer impurity can be reduced by adding methocarbamol to a buffered solution after pH adjustment instead of before.
A stable composition of methocarbamol can be a solution containing about 0.3% w/w or less of the β-isomer after storage at ambient temperature for at least 3 months.
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