A new application about 2-Methyl-1,2,3,4-tetrahydroisoquinoline

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N-methylation of nitrogen-containing organic substrates: A comprehensive overview

The present account surveys the results of the plethora of works on N-methylation of nitrogen-containing substrates, mainly amines. The countless reports in the literature on this issue reveal the emergence of a set of methylating agents, which include: methanol, dimethyl carbonate, formaldehyde/formic acid, carbon dioxide/reductant, methyl iodide, dimethylsulfate, peroxides, dimethylsulfoxide, tetramethylammonium salts, and other unusual ones. Types of the methylating agents including, catalyst, solvent, base, ligand, reducing agent and other reaction conditions such as temperature and time would greatly affect the extent of selectivity of N-monomethylation vis-a-vis N,N-dimethylation. The degree of acidity or alkalinity of catalysts such as the solid catalysts (i.e. zeolites) showed a substantial impact on the selectivity and the course of methylation, leading to design adequate catalysts or to bring suitable modifications to the existing ones. Although this account takes into consideration all types of methylating agents, it is worthwhile to mention that the relatively recent works have been focused on the utilization of eco-friendly methylating agents, including carbon dioxide/reductant, methanol, and dimethylcarbonate. N-Methyl-containing drugs were successfully synthesized with some methylating agents under specified conditions. In some instances, unexpected products and events from the planned N-methylation of some nitrogen-containing molecules occurred. N-Formylation occurred as an intermediate or concomitant reaction when amines were subjected to catalyze methylation with methanol, formaldehyde/formic acid, and carbon dioxide/reductant. The occasionally depicted mechanisms would elucidate the carbon and hydrogen sources of the affixing methyl group on the nitrogen site. Peculiarly, methylation involving methanol as a methylating agent and transition metal catalysis called for borrowing hydrogen process as a new mechanistic approach.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Brief introduction of 2-Methyl-1,2,3,4-tetrahydroisoquinoline

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Inhibition of Complex I by Isoquinoline Derivatives Structurally Related to 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine (MPTP)

Mitochondrial respiratory failure secondary to complex I inhibition may contribute to the neurodegenerative process underlying nigral cell death in Parkinson’s disease (PD). Isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) or 1-methyl-4-phenylpyridinium (MPP+) may be inhibitors of complex I, and have been implicated in the cause of PD as endogenous neurotoxins. To determine the potency and structural requirements of isoquinoline derivatives to inhibit mitochondrial function, we examined the effects of 22 neutral and quaternary compounds from three classes of isoquinoline derivatives (11 isoquinolines, 2 dihydroisoquinolines, and 9 1,2,3,4-tetrahydroisoquinolines) and MPP+ on the enzymes of the respiratory chain in mitochondrial fragments from rat forebrain. With the exception of norsalsolinol and N,n-propylisoquinolinium, all compounds inhibited complex I in a time-independent, but concentration-dependent manner, with IC50s ranging from 0.36-22 mM. Several isoquinoline derivatives were more potent inhibitors of complex I than 1-methyl-4-phenylpyridinium ion (MPP+) (IC50 = 4.1 mM), the most active being N-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline (IC50 = 0.36 mM) and 6-methoxy-1,2,3,4-tetrahydroisoquinoline (IC50 = 0.38 mM). 1,2,3,4-Tetrahydroisoquinoline was the least potent complex I inhibitor (IC50 ca. 22 mM). At 10 mM, only isoquinoline (23.1 percent), 6,7-dimethoxyisoquinoline (89.6 percent), and N-methylsalsolinol (34.8 percent) inhibited (P < 0.05) complex II-III, but none of the isoquinoline derivatives inhibited complex IV. There were no clear structure-activity relationships among the three classes of isoquinoline derivatives studied, but lipophilicity appears to be important for complex I inhibition. The effects of isoquinoline derivatives on mitochondrial function are similar to those of MPTP/MPP+, so respiratory inhibition may underlie their reported neurotoxicity. If you are interested in 1612-65-3, you can contact me at any time and look forward to more communication. SDS of cas: 1612-65-3

Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Discovery of 1612-65-3

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A novel linker strategy for solid-phase synthesis

The REM resin for solid phase synthesis is described. Its use is illustrated by preparing a small array of tertiary amines using a Hoffman elimination reaction. No functional group is required for linking these compounds onto the resin other than the amine constructed during the synthesis.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

New explortion of 2-Methyl-1,2,3,4-tetrahydroisoquinoline

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1612-65-3, Name is 2-Methyl-1,2,3,4-tetrahydroisoquinoline, belongs to tetrahydroisoquinoline compound, is a common compound. Product Details of 1612-65-3In an article, once mentioned the new application about 1612-65-3.

Pd-catalyzed ortho-arylation of 3,4-dihydroisoquinolones via C-H bond activation: synthesis of 8-aryl-1,2,3,4-tetrahydroisoquinolines

An efficient route to synthesize biologically interesting 8-aryl-1,2,3,4-tetrahydroisoquinoline has been developed. It involves the Pd-catalyzed direct arylation of 3,4-dihydroisoquinolones via C-H bond activation with aryl iodides to afford a variety of 8-arylated cross-coupling products, which are subsequently reduced to 8-aryl-1,2,3,4-tetrahydroisoquinolines in good to excellent yields.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Brief introduction of 2-Methyl-1,2,3,4-tetrahydroisoquinoline

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Total Synthesis of Tetrahydroisoquinoline-Based Bioactive Natural Products Laudanosine, Romneine, Glaucine, Dicentrine, and Their Unnatural Analogues Isolaudanosine and Isoromneine

Starting from suitably substituted homophthalic acids, total synthesis of titled alkaloids have been demonstrated in very good yields. The obtained natural products laudanosine and romneine were utilized to accomplish synthesis of two isoquinoline-based alkaloids glaucine and dicentrine. Base-induced selective generation of two different types of benzylic carbanions, their coupling reactions with 3,4-dimethoxybenzyl mesylate, and the regioselective iodination followed by intramolecular aryl-aryl coupling reactions to form the fused biaryl systems were the strategic steps.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

The important role of 2-Methyl-1,2,3,4-tetrahydroisoquinoline

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Cholinergic effects of molecular segments of apomorphine and dopaminergic effects of N,N dialkylated dopamines

The hydrochlorides of molecular segments of apomorphine [2 (3′,4′ dihydroxybenzyl) 1,2,3,4 tetrahydroisoquinoline, 2 (3′,4′ dihydroxybenzyl) piperidine, and 1,2,3,4 tetrahydroisoquinoline with their respective N methyl and N n propyl homologs] and N,N dialkylated dopamine compounds were synthesized and studied for LD50 in intact mice; stereotypy in intact mice; curving of the body in unilaterally caudectomized mice; rotation in 6 hydroxydopamine lesioned rats, and activation of adenylate cyclase in homogenates of mouse caudate nuclei. Instead of dopaminergic effects 1 (3′,4′ dihydroxybenzyl) 2 methyl 1,2,3,4, tetrahydroisoquinoline and 2 methyl 1,2,3,4, tetrahydroisoquinoline showed cholinergic ones. These effects were blocked in atropine pretreated animals. Of the N,N dialkylated dopamine compounds synthesized, the N n propyl N n butyldopamine ranked in all tests as the strongest dopamine receptor agonist and N methyl N n propyldopamine as the weakest. In contrast, N,N dimethyldopamine and 1 (3,4 dihydroxyphenylethyl) piperidine showed no dopaminergic effects. The effectiveness of the dopaminergic agonists depended on the length of the N alkyl substituents suggesting interactions with hydrophobic regions of the receptor site.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Awesome and Easy Science Experiments about 1612-65-3

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Oxidation of Trialkylamines by BrCCl3: Scope, Applications and Mechanistic Aspects

The catalyst-free photochemical reaction of trialkylamines and BrCCl3 induced by visible light was investigated. The outcome of the reaction was found to depend strongly on the nature of the amine substrates. N-Methyl-1,2,3,4-tetrahydroisoquinolines give 3,4-dihydroisoquinolinium salts, whereas aliphatic trialkylamines produce hydrohalide salts and streptocyanines as the major products. The addition of KCN inhibits streptocyanine formation, and results in the clean formation of alpha-aminonitriles instead. The light-absorbing species and the underlying reaction mechanism were studied by DFT calculations and experimental observations.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A new application about 1612-65-3

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SELECTIVE REDUCTION OF IMONIUM SALTS BY SODIUM HYDROGEN TELLURIDE

Sodium hydrogen telluride reduces imonium salts efficiently at room temperature in ethanol.The products of the reaction depend upon the pH.Under alkaline pH only dihydro-derivatives are formed.Under acid pH (6-7) the products depend on the structure of the salt.The tellurium can be recovered quantitatively.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Some scientific research about 2-Methyl-1,2,3,4-tetrahydroisoquinoline

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Basicity pK(HB) scale of hydrogen bounding of aliphatic tertiary amines

The hydrogen bond acceptor strength of 40 tertiary amines has been measured by Fourier transform – infrared (FTIR) spectrometry from their 1:1 complexation constant towards 4-fluorophenol in CCl4 at 25C (the pKHB scale). Also measured was the frequency shift, Deltanu(OH), of the nu(OH) band of methanol hydrogen-bonded to these amines. The comparison of the thermodynamic hydrogen bond basicity scale, pKHB, with the spectroscopic one, Deltanu(OH), and with the Bronsted pKa scale, points to the great sensitivity of pKHB to steric effects. The pKHB scale of tertiary amines extends from 2.71 for quinuclidine to -0.34 for N,N-diisopropyl-3-pentylamine. The main factors governing this important variation (17 kJ¡¤mol-1 on the Gibbs energy scale) are the electron-withdrawing inductive effect and various kinds of steric effects (e.g., opening of the CNC angles and hindrance to OH fixation on the nitrogen lone pair). Infrared (IR) spectra show the attachment of 4-fluorophenol to the nitrile nitrogen of Me2NCH2C?N and Me2NCH2CH2C?N, to the oxygen of N-methylmorpholine, and to the pi electrons of (HC?CCH2)3N and (PhCH2)3N, in addition to the attachment to the amino nitrogen. In (PhCH2)3N, the electron-withdrawing effect of the three benzyl substituents and, mainly, the very important congestion of the nitrogen lone pair reduce the nitrogen hydrogen-bond basicity almost to nothing, so that tribenzylamine, a nitrogen Bronsted base, turns to a pi base in hydrogen bonding. From this example, the large differences between the pKHB and pKa scales of organic bases are emphasized.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

More research is needed about 1612-65-3

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Inhibition of monoamine oxidase by isoquinoline derivatives. Qualitative and 3D-quantitative structure-activity relationships

A series of isoquinolines, N-methyl-1,2-dihydroisoquinolines, N-methyl-1,2,3,4-tetrahydroisoquinolines, 1,2,3,4-tetrahydroisoquinolines, and N-methylisoquinolinium ions were tested as inhibitors of monoamine oxidases A and B. All compounds were found to act as reversible and time-independent MAO inhibitors, often with a distinct selectivity towards MAO-A. As a class, the N-methylisoquinolinium ions were found to be the most active MAO-A inhibitors, with N-methyl-6-methoxyisoquinolinium ion emerging as a potent (IC50 = 0.81 muM) and competitive MAO-A inhibitor. Comparative molecular field analysis (CoMFA, a 3D-QSAR method) of MAO-A inhibition was performed using the data reported here and in the literature. Using the steric and lipophilic fields of the inhibitors, quantitative models with reasonable predictive power were obtained that point to the importance of steric, lipophilic, and polar interactions in modulating MAO-A inhibitory activity.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem