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Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride
Catalog Number: BT-253743
CAS Number: 6197-39-3
Molecular Formula: C7H12ClNO2
Molecular Weight: 177.63 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride (MPTP-HCl) is a chemical compound that was first synthesized in the 1970s as a byproduct of an attempt to create a synthetic opioid. However, it was later discovered that MPTP-HCl has neurotoxic effects and can cause Parkinson's disease-like symptoms in humans and animals. Since then, MPTP-HCl has been extensively studied for its biological activity and potential therapeutic applications.
Properties
CAS Number
6197-39-3
Product Name
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride
IUPAC Name
methyl 1,2,3,6-tetrahydropyridine-5-carboxylate;hydrochloride
Molecular Formula
C7H12ClNO2
Molecular Weight
177.63 g/mol
InChI
InChI=1S/C7H11NO2.ClH/c1-10-7(9)6-3-2-4-8-5-6;/h3,8H,2,4-5H2,1H3;1H
InChI Key
ZWALOEQHJRUTKM-UHFFFAOYSA-N
SMILES
COC(=O)C1=CCCNC1.Cl
Synonyms
Guvacine HCl; Guvacoline hydrochloride; Norarecoline HCl; Norarecoline hydrochloride.;1,2,5,6-Tetrahydro-3-pyridinecarboxylic acid methyl ester hydrochloride
Canonical SMILES
COC(=O)C1=CCCNC1.Cl
Method of Synthesis or Extraction
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride can be synthesized using various methods, including the Leuckart-Wallach reaction, the Mannich reaction, and the Pictet-Spengler reaction. The Leuckart-Wallach reaction involves the reaction of methylamine with 2-acetylpyridine, followed by reduction with sodium borohydride and acidification with hydrochloric acid to yield Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride. The Mannich reaction involves the reaction of 2-acetylpyridine with formaldehyde and methylamine, followed by reduction and acidification to yield Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride. The Pictet-Spengler reaction involves the reaction of tryptamine with 2-acetylpyridine, followed by reduction and acidification to yield Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride.
The efficiency and yield of each method vary depending on the reaction conditions and the purity of the starting materials. The Leuckart-Wallach reaction is the most commonly used method and yields the highest purity of Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride. However, it also produces a significant amount of waste and requires careful handling due to the use of toxic reagents. The Mannich reaction and the Pictet-Spengler reaction are less commonly used but can be more environmentally friendly and produce higher yields of Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride.
The efficiency and yield of each method vary depending on the reaction conditions and the purity of the starting materials. The Leuckart-Wallach reaction is the most commonly used method and yields the highest purity of Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride. However, it also produces a significant amount of waste and requires careful handling due to the use of toxic reagents. The Mannich reaction and the Pictet-Spengler reaction are less commonly used but can be more environmentally friendly and produce higher yields of Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride.
Chemical Structure and Biological Activity
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride has a chemical structure that consists of a pyridine ring and a tetrahydropyridine ring connected by a carboxylate group. It is a prodrug that is metabolized in the body to form MPP+, a neurotoxin that selectively damages dopaminergic neurons in the substantia nigra of the brain. This mechanism of action is similar to that of Parkinson's disease, which is characterized by the loss of dopaminergic neurons in the brain.
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride has been extensively studied for its biological activity and potential therapeutic applications. It has been shown to induce Parkinson's disease-like symptoms in humans and animals, making it a valuable tool for studying the disease and developing new treatments. It has also been studied for its potential use in cancer therapy, as it has been shown to inhibit the growth of certain cancer cells.
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride has been extensively studied for its biological activity and potential therapeutic applications. It has been shown to induce Parkinson's disease-like symptoms in humans and animals, making it a valuable tool for studying the disease and developing new treatments. It has also been studied for its potential use in cancer therapy, as it has been shown to inhibit the growth of certain cancer cells.
Biological Effects
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride has a range of biological effects on cell function and signal transduction. It selectively damages dopaminergic neurons in the brain, leading to a decrease in dopamine levels and the development of Parkinson's disease-like symptoms. It has also been shown to inhibit the growth of certain cancer cells by inducing apoptosis and inhibiting cell proliferation.
However, Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride also has potential toxic effects, as it can cause irreversible damage to dopaminergic neurons and lead to permanent neurological deficits. It is also highly toxic and can be fatal if ingested or inhaled.
However, Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride also has potential toxic effects, as it can cause irreversible damage to dopaminergic neurons and lead to permanent neurological deficits. It is also highly toxic and can be fatal if ingested or inhaled.
Applications
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride has a range of potential applications in medical, environmental, and industrial research. In medical research, it is used as a tool for studying Parkinson's disease and developing new treatments. It has also been studied for its potential use in cancer therapy.
In environmental research, Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride is used to study the effects of neurotoxins on ecosystems and to develop strategies for pollution management. It has also been studied for its potential impact on sustainability and the environment.
In industrial research, Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride is used in manufacturing processes to improve product quality and efficiency. However, its use in industrial settings requires careful handling and consideration of health and safety considerations.
In environmental research, Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride is used to study the effects of neurotoxins on ecosystems and to develop strategies for pollution management. It has also been studied for its potential impact on sustainability and the environment.
In industrial research, Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride is used in manufacturing processes to improve product quality and efficiency. However, its use in industrial settings requires careful handling and consideration of health and safety considerations.
Future Perspectives and Challenges
Despite its potential applications, the use of Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride in research is limited by its toxicity and potential for harm. Future research will need to focus on developing safer and more effective methods for studying Parkinson's disease and other neurological disorders. This may involve the development of new compounds that mimic the effects of Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride without its toxic effects.
In addition, there is a need for more research on the environmental and industrial impacts of Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride. This will require a better understanding of its potential effects on ecosystems and the environment, as well as the development of safer and more sustainable manufacturing processes.
Conclusion:
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride (Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride) is a chemical compound that has been extensively studied for its biological activity and potential therapeutic applications. It has a range of potential applications in medical, environmental, and industrial research, but its use is limited by its toxicity and potential for harm. Future research will need to focus on developing safer and more effective methods for studying Parkinson's disease and other neurological disorders, as well as understanding its potential impact on the environment and industry.
In addition, there is a need for more research on the environmental and industrial impacts of Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride. This will require a better understanding of its potential effects on ecosystems and the environment, as well as the development of safer and more sustainable manufacturing processes.
Conclusion:
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride (Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride) is a chemical compound that has been extensively studied for its biological activity and potential therapeutic applications. It has a range of potential applications in medical, environmental, and industrial research, but its use is limited by its toxicity and potential for harm. Future research will need to focus on developing safer and more effective methods for studying Parkinson's disease and other neurological disorders, as well as understanding its potential impact on the environment and industry.
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