6543-83-5

Basic information

• Product Name: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-1-carboxylic acid
• Synonyms: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-1-carboxylic acid;1,2,3,4-tetrahydro-1-methyl-beta-carboline-1-carboxylic acid
• CAS NO: 6543-83-5
• Molecular Formula: C₁₃H₁₄N₂O₂
• Molecular Weight: 230.26246
• EINECS: 229-459-7
• Mol File: 6543-83-5.mol

Chemical Properties

• Boiling Point: 474°C at 760 mmHg
• Flash Point: 240.5°C
• Appearance: /
• Density: 1.312g/cm³
• Vapor Pressure: 8.6E-10mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-1-carboxylic acid(6543-83-5)
• EPA Substance Registry System: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-1-carboxylic acid(6543-83-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 6543-83-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-1-carboxylic acid is used as a precursor or active ingredient in the development of drugs and medicines due to its alkaloid nature and potential bioactivity. Its specific role in therapeutic applications may vary, but the compound's structural features suggest it could be involved in the treatment of various conditions, pending further research and clinical validation.
Used in Research and Development:
In the field of scientific research, 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-1-carboxylic acid serves as a subject for exploration into its chemical properties, synthesis methods, and potential applications. Ongoing studies may focus on understanding its interactions with biological systems, mechanisms of action, and optimization for specific therapeutic uses.

InChI:InChI=1/C13H14N2O2/c1-13(12(16)17)11-9(6-7-14-13)8-4-2-3-5-10(8)15-11/h2-5,14-15H,6-7H2,1H3,(H,16,17)

Upstream product

• 343-94-2 tryptamine hydochloride 
• 127-17-3 2-oxo-propionic acid 
• 67-56-1 methanol 
• 76673-76-2 ethyl 1-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-carboxylate 
• 113-24-6 sodium pyruvate 

Downstream Products

• 2506-10-7 eleagnine 

Relevant articles and documents

Bromal-derived tetrahydro-β-carbolines as neurotoxic agents: Chemistry, impairment of the dopamine metabolism, and inhibitory effects on mitochondrial respiration

The mammalian alkaloids tryptoline (1) and eleagnine (2) as well as the highly halogenated (X=F, Cl, Br) tetrahydro-β-carbolines (THβCs) 3-5, structurally similar to the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP, 6), were found to have a common feature of inducing a severe impairment of the nigrostriatal dopamine metabolism and inhibiting complex I of the mitochondrial respiratory chain highly selectively. Within the series of compounds tested, 1-tribromomethyl-1,2,3,4-tetrahydro-β-carboline ('TaBro', 5), which was prepared in high yields from the biogenic amine tryptamine ('Ta', 7) and the unnatural aldehyde bromal ('Bro', 8) by a Pictet-Spengler cyclization reaction, turned out to be the most potent toxin in vitro and in vivo. As demonstrated by voltammetric measurements on rats, for all the THβCs 1-5 investigated, intranigral application of a single dose of 10μg resulted in a significant reduction of the dopaminergic activity in the striatum, with the strongest effect being observed for TaBro (5). Using rat brain homogenates, again 5 (IC50=200μM) as well as its dehydrohalogenation product 11 (IC50=150μM) exhibited the most pronounced inhibitory potential on mitochondrial respiration. The halogen-free THβCs 1 and 2 as well as the MPTP metabolite 1-methyl-4-phenylpyridinium ion (MPP+), by contrast, showed only a moderate inhibition at concentrations in the millimolar range (e.g. for MPP+: IC50=3.5mM). For an elucidation of the role of hydrophobic portion in the inhibitory action against complex I activity, several N-acyl derivatives (15-21) of 5 were synthesized and tested. An X-ray diffraction study on the 3-dimensional structure of trifluoroacetylated highly halogenated THβCs (12-14) revealed the tetrahydropyrido part to adopt a nearly planarized half-chair conformation. Because of the steric demand of the trihalogenmethyl moiety (CF333), the N-substituent is dramatically pushed out of that ring 'plane'. Copyright (C) 2000 Elsevier Science Ltd.

Electrochemistry of Natural Products. 7. Oxidative Decarboxylation of Some Tetrahydro-β-carbolinecarboxylic Acids

A series of 1,2,3,4-tetrahydro-β-carboline-1- and -3-carboxylic acids containing various substituents in positions 1, 2, and 3 were oxidized electrochemically.In general, the acids were decarboxylated, and unsaturation was introduced into the C ring.The oxidation appears to take place through the indole ring nitrogen, and possible mechanisms of the reactions are presented.Parallels between the observed reactions and early steps in indole alkaloid biosynthesis are discussed.The oxidative dimerization of tetrahydrocarbazole is reported.