10022-82-9

Basic information

• Product Name: 1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid
• Synonyms: 1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid
• CAS NO: 10022-82-9
• Molecular Formula: C₁₃H₁₂N₂O₂
• Molecular Weight: 0
• Mol File: 10022-82-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 522.5°Cat760mmHg
• Flash Point: 269.8°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.712
• CAS DataBase Reference: 1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid(10022-82-9)
• EPA Substance Registry System: 1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid(10022-82-9)

Safety Data

• Hazardous Substances Data: 10022-82-9(Hazardous Substances Data)

Usage

General Description

1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid is a chemical compound that belongs to the beta-carboline class of compounds. It is a derivative of the neurotransmitter serotonin and has been studied for its potential neuroprotective and antioxidant properties. 1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid has also been investigated for its potential to modulate the activity of the central nervous system and has shown potential in the treatment of neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease. Additionally, it has been studied for its potential as an anti-cancer agent and for its role in regulating the immune system. Further research is needed to fully understand the pharmacological properties and potential therapeutic uses of 1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid.

InChI:InChI=1/C13H12N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,11,15H,6H2,1H3,(H,16,17)

Upstream product

• 54-12-6 Trp 
• 5379-97-5 acetylamino-indol-3-ylmethyl-malonic acid diethyl ester 
• 1218-34-4 N-α-acetyltryptophan 
• 73-22-3 L-Tryptophan 
• 78-98-8 2-oxopropanal 
• 5470-37-1 1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid 
• 99437-65-7 4-indol-3-ylmethyl-2-methyl-4H-oxazol-5-one 
• 1218-34-4 N-acetyl-DL-tryptophan 
• 1218-34-4 N-AcTrp 
• 73198-02-4 optically inactive 1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid 
• 75-36-5 acetyl chloride 
• 102016-94-4 1-methyl-4,9-dihydro-β-carboline-3,3-dicarboxylic acid diethyl ester 

Downstream Products

• 22329-38-0 harman-3-carboxylic acid 
• 93712-59-5 1-methyl-4,9-dihydro-3H-β-carboline-3-carboxylic acid methyl ester 
• 119645-76-0 1-[2-Hydroxy-2-(2-sulfo-phenyl)-ethyl]-4,9-dihydro-3H-β-carboline-3-carboxylic acid 

Relevant articles and documents

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Degradation of tetrahydro-β-carbolines in the presence of nitrite: HPLC-MS analysis of the reaction products

Motivated by the identification of numerous novel tetrahydro-β-carboline-carboxylic acids in food samples, we studied the reactions of tetrahydro-β-carbolines in the presence of nitrosating agents. The anticipated formation of nitroso derivatives from unsubstituted tetrahydro-β-carbolines, and from tetrahydro-β-carboline-3-carboxylic acids was indicated by HPLC-MS/MS analysis and validated by the characteristic product ion spectra of the respective nitroso compounds. In addition, oxidative decarboxylation resulted in formation of the corresponding dihydro-β-carbolines, and in the generation of the β-carbolines harman or norharman. Subsequently, we studied the reactivity of tetrahydro-β-carboline-1-carboxylic acids derived from the Pictet-Spengler condensation of indole amines with α-oxo acids. Again, in the presence of nitrosating agents the rapid disappearance of the starting material was obvious, but no nitroso derivatives could be observed. Instead, further HPLC-MS/MS studies demonstrated that dihydro-β-carbolines were the major products of tetrahydro-β-carboline-1-carboxylic acids. Finally, we demonstrated that freshly isolated nitroso-precursors spontaneously decomposed to yield harman alkaloids. In conclusion, we revealed that nitroso-tetrahydro-β-carbolines can represent intermediates involved in the generation of β-carbolines, and we established a novel pathway for the formation of harman alkaloids from nutritional tetrahydro-β-carbolines.

Aromatization and chemoselective alkylation of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid and its derivatives

Unprecedented aromatization was observed during N-alkylation reactions of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid methyl ester, giving rise to 9-alkyl-1-methyl-β-carboline-3-carboxylic acid methyl esters. Inverse addition of base during a simil