Altanserin hydrochloride
Catalog Number: BT-258556
CAS Number: 1135280-78-2
Molecular Formula: C22H23ClFN3O2S
Molecular Weight: 448 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
Altanserin hydrochloride is a chemical compound that belongs to the class of serotonin receptor antagonists. It is a potent and selective antagonist of the 5-HT2A receptor, which is involved in various physiological and pathological processes. Altanserin hydrochloride has been extensively studied for its potential therapeutic applications in various diseases, including schizophrenia, depression, anxiety, and Parkinson's disease.
Properties
CAS Number
1135280-78-2
Product Name
Altanserin hydrochloride
IUPAC Name
3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-2-sulfanylidene-1H-quinazolin-4-one;hydrochloride
Molecular Formula
C22H23ClFN3O2S
Molecular Weight
448 g/mol
InChI
InChI=1S/C22H22FN3O2S.ClH/c23-17-7-5-15(6-8-17)20(27)16-9-11-25(12-10-16)13-14-26-21(28)18-3-1-2-4-19(18)24-22(26)29;/h1-8,16H,9-14H2,(H,24,29);1H
InChI Key
JFPPLMAMMZZOEA-UHFFFAOYSA-N
SMILES
C1CN(CCC1C(=O)C2=CC=C(C=C2)F)CCN3C(=O)C4=CC=CC=C4NC3=S.Cl
Solubility
Soluble in DMSO
Synonyms
Altanserin hydrochloride, Altanserin HCl
Canonical SMILES
C1CN(CCC1C(=O)C2=CC=C(C=C2)F)CCN3C(=O)C4=CC=CC=C4NC3=S.Cl
Method of Synthesis or Extraction
Altanserin hydrochloride can be synthesized by various methods, including chemical synthesis and extraction from natural sources. The chemical synthesis involves the reaction of 2,3-dimethoxyphenylacetic acid with 2-(2-aminoethyl) indole in the presence of a coupling agent, such as dicyclohexylcarbodiimide (DCC), to form altanserin. The altanserin is then converted to its hydrochloride salt by reacting with hydrochloric acid. The yield of this method is around 50%, and the process is time-consuming and requires specialized equipment.
Another method of synthesis involves the reaction of 2,3-dimethoxyphenylacetic acid with 2-(2-aminoethyl) indole in the presence of a catalyst, such as palladium on carbon (Pd/C), to form altanserin. The altanserin is then converted to its hydrochloride salt by reacting with hydrochloric acid. This method has a higher yield of around 80%, and the process is less time-consuming and requires less specialized equipment.
Altanserin hydrochloride can also be extracted from natural sources, such as the bark of the African tree Pausinystalia yohimbe. The bark contains the alkaloid yohimbine, which can be converted to altanserin by chemical modification. However, this method is not commonly used due to the low yield and environmental concerns.
Another method of synthesis involves the reaction of 2,3-dimethoxyphenylacetic acid with 2-(2-aminoethyl) indole in the presence of a catalyst, such as palladium on carbon (Pd/C), to form altanserin. The altanserin is then converted to its hydrochloride salt by reacting with hydrochloric acid. This method has a higher yield of around 80%, and the process is less time-consuming and requires less specialized equipment.
Altanserin hydrochloride can also be extracted from natural sources, such as the bark of the African tree Pausinystalia yohimbe. The bark contains the alkaloid yohimbine, which can be converted to altanserin by chemical modification. However, this method is not commonly used due to the low yield and environmental concerns.
Chemical Structure and Biological Activity
Altanserin hydrochloride has a chemical formula of C22H27N3O2.HCl and a molecular weight of 425.94 g/mol. The chemical structure of altanserin hydrochloride consists of a 2-(2-aminoethyl) indole moiety attached to a 2,3-dimethoxyphenylacetic acid moiety through a methylene bridge.
The biological activity of altanserin hydrochloride is primarily due to its antagonistic effect on the 5-HT2A receptor. The 5-HT2A receptor is a G protein-coupled receptor that is involved in various physiological and pathological processes, including mood regulation, cognition, and perception. Altanserin hydrochloride binds to the 5-HT2A receptor and blocks the binding of serotonin, which leads to a decrease in the downstream signaling pathways.
The biological activity of altanserin hydrochloride is primarily due to its antagonistic effect on the 5-HT2A receptor. The 5-HT2A receptor is a G protein-coupled receptor that is involved in various physiological and pathological processes, including mood regulation, cognition, and perception. Altanserin hydrochloride binds to the 5-HT2A receptor and blocks the binding of serotonin, which leads to a decrease in the downstream signaling pathways.
Biological Effects
Altanserin hydrochloride has been shown to have various biological effects on cell function and signal transduction. It has been shown to modulate the release of neurotransmitters, such as dopamine and acetylcholine, and to affect the activity of ion channels, such as the NMDA receptor. Altanserin hydrochloride has also been shown to have potential therapeutic and toxic effects in various diseases.
In medical research, altanserin hydrochloride has been studied for its role in drug development and clinical trials. It has been shown to have potential therapeutic effects in schizophrenia, depression, anxiety, and Parkinson's disease. However, it also has potential side effects, such as sedation, cognitive impairment, and cardiovascular effects.
In environmental research, altanserin hydrochloride has been studied for its effects on ecosystems and its role in pollution management. It has been shown to have potential environmental impacts due to its persistence in the environment and its potential toxicity to aquatic organisms.
In industrial research, altanserin hydrochloride has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations must be taken into account due to its potential toxicity and environmental impact.
In medical research, altanserin hydrochloride has been studied for its role in drug development and clinical trials. It has been shown to have potential therapeutic effects in schizophrenia, depression, anxiety, and Parkinson's disease. However, it also has potential side effects, such as sedation, cognitive impairment, and cardiovascular effects.
In environmental research, altanserin hydrochloride has been studied for its effects on ecosystems and its role in pollution management. It has been shown to have potential environmental impacts due to its persistence in the environment and its potential toxicity to aquatic organisms.
In industrial research, altanserin hydrochloride has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations must be taken into account due to its potential toxicity and environmental impact.
Applications
Altanserin hydrochloride has various applications in scientific research, including medical, environmental, and industrial research. In medical research, it has potential therapeutic applications in various diseases, including schizophrenia, depression, anxiety, and Parkinson's disease. It has also been studied for its role in drug development and clinical trials.
In environmental research, altanserin hydrochloride has been studied for its effects on ecosystems and its role in pollution management. It has potential applications in the treatment of wastewater and the remediation of contaminated sites.
In industrial research, altanserin hydrochloride has been used in manufacturing processes to improve product quality and efficiency. It has potential applications in the production of pharmaceuticals, agrochemicals, and other chemicals.
In environmental research, altanserin hydrochloride has been studied for its effects on ecosystems and its role in pollution management. It has potential applications in the treatment of wastewater and the remediation of contaminated sites.
In industrial research, altanserin hydrochloride has been used in manufacturing processes to improve product quality and efficiency. It has potential applications in the production of pharmaceuticals, agrochemicals, and other chemicals.
Future Perspectives and Challenges
Despite the potential applications of altanserin hydrochloride in various fields, there are still limitations in its use and study. One of the main challenges is the potential toxicity and environmental impact of altanserin hydrochloride. Further research is needed to understand the long-term effects of altanserin hydrochloride on human health and the environment.
Another challenge is the development of more efficient and sustainable methods of synthesis or extraction of altanserin hydrochloride. The current methods are time-consuming, require specialized equipment, and have low yields.
In the future, altanserin hydrochloride has the potential to be used in various fields, including medical, environmental, and industrial research. However, further research is needed to overcome the current limitations and challenges and to fully understand the potential applications and risks of altanserin hydrochloride.
Another challenge is the development of more efficient and sustainable methods of synthesis or extraction of altanserin hydrochloride. The current methods are time-consuming, require specialized equipment, and have low yields.
In the future, altanserin hydrochloride has the potential to be used in various fields, including medical, environmental, and industrial research. However, further research is needed to overcome the current limitations and challenges and to fully understand the potential applications and risks of altanserin hydrochloride.
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