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

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

Uses

Used in Pharmaceutical Industry:
1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid is used as a neuroprotective agent for its potential to protect neurons from damage and degeneration, particularly in neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease.
1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid is used as an antioxidant agent for its potential to neutralize harmful free radicals and protect cells from oxidative stress, which may contribute to the development of various diseases.
Used in Neurodegenerative Disease Treatment:
1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid is used as a therapeutic agent for its potential to modulate the activity of the central nervous system and treat neurodegenerative diseases by protecting neurons and reducing oxidative stress.
Used in Cancer Research:
1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid is used as an anti-cancer agent for its potential to inhibit the growth and proliferation of cancer cells, with further research needed to fully understand its pharmacological properties and therapeutic uses in cancer treatment.
Used in Immune System Regulation:
1-methyl-3,4-dihydro-beta-carboline-3-carboxylic acid is used as an immunomodulatory agent for its potential role in regulating the immune system, with further research needed to explore its specific applications and mechanisms of action in immune-related conditions.

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

• 73198-02-4 optically inactive 1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid 
• 1218-34-4 N-AcTrp 
• 1218-34-4 N-acetyl-DL-tryptophan 
• 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 
• 75-36-5 acetyl chloride 
• 102016-94-4 1-methyl-4,9-dihydro-β-carboline-3,3-dicarboxylic acid diethyl ester 

Downstream Products

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

Relevant articles and documents

Isolation of mutagenic β-carboline derivatives after nitrite treatment of maillard reaction mixtures and analysis of these compounds from foodstuffs and human urine

Mixtures of carbohydrate decomposition products and L-tryptophan were incubated at pH 7.0 and 37°C for 4 weeks. These mixtures exhibited mutagenic activity toward S. typhimurium TA 100 without metabolic activation after a nitrite treatment at pH 4.0. Four β-carboline derivatives were isolated as premutagens from mixtures of methylglyoxal and furfural. These premutagens were also found to be contained in daily foodstuffs and human urine samples.

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.

Synthesis and evaluation of β-carboline derivatives as inhibitors of human immunodeficiency virus

A series of β-carboline derivatives were synthesized by utilizing aromatization and chemoselective alkylation method recently reported from our laboratory. Synthesized derivatives were evaluated for anti-HIV activity in human CD4+ T cell line (CEM-GFP) infected with HIV-1 NL4.3 virus. 1-Formyl-β-carboline-3-carbxylic acid methyl ester (15) showed inhibition of human immunodeficiency virus at IC50 = 2.9 μM.

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

Derivatives of 3,4-dihydro-β-carboline-3-carboxylic acid from C-terminal tryptophan-containing peptides. Synthesis and properties

C-terminal tryptophan containing peptides have been converted into 1-peptidyl-3,4-dihydro-β-carboline-3-carboxylic acids by acid catalyzed isomerization of their azlactone derivatives. The main properties of these abnormal peptides are a strong absorption around 360 nm an intense fluoroscence and ability to generate reactive carbanions when dissolved in basic media. This tryptophan conversion takes place with high yield and is of general applicability.