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1-Hydroxymethylbenzotriazole reacts with phenylethylamines to give the respective N,N-bis(benzotriazol-1-ylmethyl)phenylethylamines, which are then subject to an intramolecular Friedel-Crafts cyclisation at room temperature to yield N-benzotriazol-1-ylmethyl-1,2,3,4-tetrahydroisoquinolines. These crystalline UV- and oxygen-stable products can be reduced at room temperature to the corresponding N-methyl-1,2,3,4-tetrahydroisoquinoIines using NaBH4. The method offers an elegant approach to a wide range of N-methylated 1,2,3,4-tetrahydroisoquinolines since it can be applied not only for the synthesis of 1,2,3,4-tetrahydroisoquinolines with electron-donating substituents on the aromatic moiety, but also for deactivated derivatives. All steps involved work under very mild conditions in high to excellent yields.

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

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New Advances in Chemical Research, May 2021.Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. category: tetrahydroisoquinoline, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 1612-65-3, name is 2-Methyl-1,2,3,4-tetrahydroisoquinoline. In an article,Which mentioned a new discovery about 1612-65-3

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) induces parkinsonism in humans after its oxidation into 1-methyl-4-phenylpyridinium ion (MPP+) by type B monoamine oxidase. The 1-amino analogues of MPTP and MPP+, 1-amino- 4-phenyl-1,2,3,6-tetrahydropyridine (APTP) and 1-amino-4-phenylpyridinium ion (APP+), were synthesized, and their cytotoxicity to clonal pheochromocytoma PC12 cells was examined using a tetrazolium formazan assay. After incubation for 48 and 72 h, both APP+ and APTP were found to be cytotoxic to PC12 cells, whereas with the N-methyl analogues, only MPP+, but not MPTP, was cytotoxic. The cytotoxicity of APTP increased with incubation time and equaled that of MPP+ after 72 h. It was found that APTP was oxidized to APP+ by type A monoamine oxidase in PC12 cells, suggesting that APP+ itself may damage the cells. In addition to APTP and APP+, N-amino analogues of N- methylisoquinolines and related derivatives were also synthesized and examined for their cytotoxicity to PC12 cells.

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

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Flavin-containing monooxygenase (FMO) was partially purified from rat brain microsomes through two successive chromatographies on columns of DEAE Sepharose and 2′,5′-ADP Sepharose. The specific activity, benzydamine N- oxidation of partially purified brain FMO, was 122-fold higher than that of microsomes. A single band of 60 kDa was recognized by Western blotting analysis with anti-rat liver FMO. The K(m) value of brain FMO for thiourea was 4-fold lower, but that for cysteamine was 10-fold higher than that of liver FMO. The enzymatic activity for n-octylamine was detected in neither brain nor liver FMO. Kinetic analysis for neurotoxins also revealed that K(m) values of brain FMO for 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), 1,2,3,4-tetrahydroisoquinoline (TIQ) and N-methyl TIQ (NMTIQ) were lower than those of liver FMO. These results indicate that rat brain FMO catalyzes several substrates of liver FMO involving neurotoxins, but it seems likely that the kinetic properties of brain FMO are somewhat different from those of liver FMO.

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

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A reliable enthalpic scale of hydrogen-bond acceptor strength (basicity) is built for aliphatic amines by means of a new infrared method, from the temperature variation of hydrogen-bond equilibrium constants. Enthalpies of hydrogen bonding to a reference hydrogen-bond acceptor, 4-fluorophenol, have been determined in CCl4 and/or C2C14 for ammonia and 68 primary, secondary, and tertiary amines. The scale spans from -23.8 kJ mol -1 for i-Pr2NCH(Et)2 to -39.4 kJ mol -1 for Et3N. This large variation is mainly explained by the basicity-enhancing electronic effects of alkyl groups, which can be overcompensated by dramatic basicity-decreasing steric effects. Relationships between DeltaH and the change in electronic energy or the infrared shift of the OH stretching upon hydrogen bonding are studied and found useful in the prediction of the hydrogen bond enthalpies of amines with several hydrogen-bond acceptor sites. A careful statistical analysis of the enthalpy-entropy relationship shows an isoentropic tendency. The entropies of 65% of hydrogen-bonding reactions between aliphatic amines and 4-fluorophenol have a mean value of -55.1 ± 4.2 J K-1 mol-1. Amines excluded from the isoentropic set are mainly severely hindered ones. The hydrogen-bond enthalpic scale can be useful in measuring the electrostatic character of Lewis bases.

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

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The present invention relates to a method for preparing alkylamines using carbon monoxide and the use of this method in the manufacturing of vitamins, pharmaceutical products, adhesives, acrylic fibres and synthetic leathers, pesticides, surfactants, detergents and fertilisers. It also relates to a method for manufacturing vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides, surfactants, detergents and fertilisers, comprising a step of preparing alkylamines by the method according to the invention. The present invention further relates to a method for preparing marked alkylamines and uses thereof.

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

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Chemical Research Letters, May 2021. Related Products of 1612-65-3, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.1612-65-3, Name is 2-Methyl-1,2,3,4-tetrahydroisoquinoline, molecular formula is C10H13N. In a Article,once mentioned of 1612-65-3

Structural modification of the tetrahydroisoquinoline (THIQ) framework is of significant interest to organic chemists due to its central role in heterocyclic and medicinal chemistry. Here we demonstrate an efficient metal-free method for the oxidative functionalization of THIQs at the C1 position, which is amenable to a diverse range of C-C coupling reactions. These reactions proceed through a hydride abstraction involving the tropylium ion followed by quenching the generated iminium intermediates with nucleophiles to afford THIQ derivatives with excellent efficiencies and interesting selectivities.

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

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The replacement of N-methyl of N-methylpiperidine (1), 4-methylmorpholine (4), 2-methyl-1,2,3,4-tetrahydroisoquinoline (7) and tropine (10) by n-propyl, n-butyl and isopropyl groups (3a-3c, 6c, 9a-9c and 12a-12c) has been achieved in high yields by quaternization of the respective tertiary amine with appropriate alkyl halide and demethylation of the resulting quaternary salt with thiophenoxide.It has been established that demethylation is strongly favoured over the removal of n-propyl and n-butyl groups, whereas deisopropylation occurs to some extent.Surprisingly, in the case of 11c, deisopropylation predominates.This method has been applied to morphine (13b), codeine (13d) and thebaine (14b) for similar replacements.The rapid quaternization of thebaine (14b) has been assigned to the absence of H-14 in this alkaloid.The fact that quaternary salts of thebaine, which are susceptible to aromatization of the nucleus by extrusion of the ethanamine chain, are smoothly demethylated to N-alkylnorthebaines (18a-18c) in good yields indicates that demethylation, a bimolecular nucleophilic displacement, competes very successfully with elimination reaction.

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

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Tropylium ion mediated alpha-cyanation of amines is described. Even in the presence of KCN, tropylium ion is capable of oxidizing various amine substrates, and the resulting iminium ions undergo salt metathesis with cyanide ion to produce aminonitriles. The byproducts of this transformation are simply cycloheptatriene, a volatile hydrocarbon, and water-soluble potassium tetrafluoroborate. Thirteen total substrates are shown for the alpha-cyanation procedure, including a gram scale synthesis of 17beta-cyanosparteine. In addition, a tropylium ion mediated oxidative aza-Cope rearrangement is demonstrated.

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

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L-Selectride(R) was shown to selectively cleave methyl carbamates in the presence of more sterically demanding carbamates, including the selective cleavage of a methyl carbamate in the presence of an N-Boc group.

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

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New Advances in Chemical Research, May 2021. The appropriate choice of redox mediator can avoid electrode passivation and overpotential, which strongly inhibit the efficient activation of substrates in electrolysis. Formula: C10H13N, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 1612-65-3, name is 2-Methyl-1,2,3,4-tetrahydroisoquinoline. In an article,Which mentioned a new discovery about 1612-65-3

Isoquinoline derivatives exert 1-methyl-4-phenylpyridinium (MPP+)-like inhibitors of complex 1 and alpha-ketoglutarate dehydrogenase activity in rat brain mitochondrial fragments. We now examine the ability of 19 isoquinoline derivatives and MPP+ to accumulate and inhibit respiration in intact rat liver mitochondria, assessed using polygraphic techniques. None of the compounds examined inhibited respiration supported by either succinate + rotenone or tertramethylparaphenylenediamne (TMPD) + ascorbate. However, with glutamate + malate as substrates, 15 isoquinoline derivatives and MPP+ inhibited states 3 and, to a lesser extent, state 4 respiration in a time- dependent manner. None of the isoquinoline derivatives were more potent than MPP+. 6,7-Dimethoxy-1-styryl-3,4-dihydroisoquinolein uncoupled mitochondrial respiration. Qualitative structure-activity relationship studies revealed that isoquinoliniumcations were more active than isoquinolines in inhibiting mitochondrial respiration; these, in turn, were more active than dihydroisoquinolines and 1,2,3,4-tertrahydroisoquinoline. Three-dimensional quantitative structure-activity relationship studies using Comparative Molecular Field Analysis showed that the inhibitor potence of isoquinoline derivatives was determined by stearic, rather than electrostatic, properties of the compounds. A hypothetical binding site was identified that may be related to a rate-limiting transport process, rather than to enzyme inhibition. In conclusion, isoquinoline derivatives are less potent in inhibiting respiration in intact mitochondria than impairing complex I activity in mitochondrial fragments. This suggests that isoquinoline derivatives are not accumulated by mitochondria as avidly as MPP+. The activity of charged and neutral isoquinoline derivatives implicates both active and passive processes by which these compounds enter mitochondria, although the quaternary nitrogen motety of the isoquinolinium cations favors mitochondrial accumulation and inhibition of respiration. These findings suggest that isoquinoline derivatives may exert mitochondrial toxicity in vivo similar to that of MPTP/MPP+.

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