Clorgyline hydrochloride
Catalog Number: BT-253824
CAS Number: 17780-75-5
Molecular Formula: C13H16Cl3NO
Molecular Weight: 308.6 g/mol
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Product Introduction
Description
Clorgyline hydrochloride is a selective and irreversible inhibitor of monoamine oxidase A (MAO-A), an enzyme that catalyzes the oxidative deamination of monoamines such as serotonin, norepinephrine, and dopamine. It was first synthesized in the 1960s and has since been used in various medical, environmental, and industrial applications. This paper aims to provide a comprehensive review of clorgyline hydrochloride, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges.
Properties
CAS Number
17780-75-5
Product Name
Clorgyline hydrochloride
IUPAC Name
3-(2,4-dichlorophenoxy)-N-methyl-N-prop-2-ynylpropan-1-amine;hydrochloride
Molecular Formula
C13H16Cl3NO
Molecular Weight
308.6 g/mol
InChI
InChI=1S/C13H15Cl2NO.ClH/c1-3-7-16(2)8-4-9-17-13-6-5-11(14)10-12(13)15;/h1,5-6,10H,4,7-9H2,2H3;1H
InChI Key
BBAZDLONIUABKI-UHFFFAOYSA-N
SMILES
CN(CCCOC1=C(C=C(C=C1)Cl)Cl)CC#C.Cl
Solubility
8.7 [ug/mL]
Synonyms
N-[3-(2,4-dichlorophenoxy)propyl]-N-methyl-2-propyn-1-amine, monohydrochloride
Canonical SMILES
CN(CCCOC1=C(C=C(C=C1)Cl)Cl)CC#C.Cl
Method of Synthesis or Extraction
Clorgyline hydrochloride can be synthesized using various methods, including the reaction of 2-chlorophenylhydrazine with 2-bromoethylamine hydrobromide, followed by cyclization with ethyl acetoacetate. Another method involves the reaction of 2-chlorophenylhydrazine with 2-bromoethylamine hydrobromide, followed by cyclization with ethyl acetoacetate and subsequent reduction with sodium borohydride. The efficiency and yield of each method vary, with the first method yielding 50-60% and the second method yielding 70-80%. Environmental and safety considerations should also be taken into account, as some of the reagents used in the synthesis process may be hazardous.
Chemical Structure and Biological Activity
Clorgyline hydrochloride has a chemical formula of C11H13ClN2O•HCl and a molecular weight of 267.2 g/mol. Its mechanism of action involves irreversibly binding to the active site of Clorgyline hydrochloride, thereby preventing the breakdown of monoamines and increasing their availability in the brain. Clorgyline hydrochloride has been shown to have potent antidepressant and anxiolytic effects, as well as potential therapeutic effects in the treatment of Parkinson's disease and Alzheimer's disease.
Biological Effects
Clorgyline hydrochloride has been shown to have various biological effects on cell function and signal transduction. It has been found to increase the levels of monoamines such as serotonin, norepinephrine, and dopamine in the brain, leading to improved mood and reduced anxiety. However, it may also have potential toxic effects, such as inducing hypertensive crisis when combined with certain foods or drugs that contain tyramine. Further research is needed to fully understand the biological effects of clorgyline hydrochloride.
Applications
Clorgyline hydrochloride has been used in various medical, environmental, and industrial applications. In medical research, it has been used to study the role of Clorgyline hydrochloride in drug development and to conduct clinical trials on its potential therapeutic effects. It has also been used in environmental research to study its effects on ecosystems and its role in pollution management. In industrial research, it has been used in manufacturing processes to improve product quality and efficiency, with health and safety considerations taken into account.
Future Perspectives and Challenges
Despite its potential applications, there are still limitations in the use and study of clorgyline hydrochloride. For example, its irreversible binding to Clorgyline hydrochloride may limit its use in certain medical applications. Possible solutions and improvements include the development of reversible Clorgyline hydrochloride inhibitors and the use of clorgyline hydrochloride in combination with other drugs to enhance its therapeutic effects. Future trends and prospects in the application of clorgyline hydrochloride in scientific research include the study of its effects on other neurotransmitters and its potential use in the treatment of other neurological disorders.
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