75626-12-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride is used as a research chemical for the development of drugs targeting dopamine release. Its ability to inhibit dopamine release induced by methamphetamine makes it a potential candidate for the treatment of addiction and related disorders.
Used in Neurochemistry Research:
As a methamphetamine-induced dopamine release inhibitor, 4-Phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride is utilized in neurochemistry research to study the mechanisms of dopamine release and the effects of its modulation on the central nervous system. This research can contribute to the development of new therapeutic strategies for neurological and psychiatric conditions.

InChI:InChI=1/C15H15N.ClH/c1-2-6-12(7-3-1)15-11-16-10-13-8-4-5-9-14(13)15;/h1-9,15-16H,10-11H2;1H

Upstream product

• 19571-30-3 4-phenylisoquinoline 
• 6187-58-2 3,4-dihydro-4-phenylisoquinoline 
• 100-46-9 benzylamine 
• 133390-25-7 2-[(2-Amino-benzyl)-benzyl-amino]-1-phenyl-ethanol 
• 215391-96-1 rac-2-(N-tert-Butoxycarbonyl-N-benzylamino)-1-phenylethanol 
• 133406-89-0 2-(o-aminobenzyl)-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 133390-35-9 2-[Benzyl-(2-nitro-benzyl)-amino]-1-phenyl-ethanol 
• 133390-34-8 2-[Benzyl-(2-nitro-benzyl)-amino]-1-phenyl-ethanone 
• 911291-94-6 benzyl-(2-nitro-benzyliden)-amine 
• 95982-61-9 o-nitro-N-benzyl(benzylamine) 
• 3433-15-6 rac-5-phenyl-1,3-oxazolidine-2-thione 
• 81316-48-5 2-(methylthio)-5-phenyl-2-oxazoline 
• 96-09-3 styrene oxide 
• 73771-35-4 3-(methylsulfanyl)benzaldehyde 

Downstream Products

• 129384-38-9 ((S)-1-tert-Butoxymethyl-2-methyl-propyl)-[1-(4-phenyl-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-amine 
• 6187-58-2 3,4-dihydro-4-phenylisoquinoline 
• 6109-35-9 1,2,3,4-tetrahydro-4-phenylisoquinoline hydrochloride 
• 28102-51-4 1,2,3,4-tetrahydro-2-methyl-4-phenylisoquinoline 
• 1310370-73-0 2-butanoyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1310370-68-3 2-(3,3-dimethylbutanoyl)-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1057137-26-4 2-(4-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)acetonitrile 
• 28102-51-4 (4S*)-N-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 213842-75-2 (R)-N-methyl-4-(phenyldeuterio)-1,2,3,4-tetrahydroisoquinoline 1-d1 
• 153218-97-4 (4S)-(-)-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 89160-45-2 (4R)-(+)-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 133390-37-1 ethyl 4-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 129353-85-1 (1S,4R)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenyl-1,2,3,4-tetrahydro-isoquinoline 
• 129353-84-0 (1S,4S)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenyl-1,2,3,4-tetrahydro-isoquinoline 

Relevant academic research and scientific papers

Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines

An efficient zinc(II)-catalyzed alkyne oxidation/C￡H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.

Weinreb amide based synthetic equivalents for convenient access to 4-aryl-1,2,3,4-tetrahydroisoquinolines

New synthetic equivalents, N-methoxy-N-methyl-N′-phenylsulfonyl glycinamide and N-methoxy-N-methyl-N′-benzyl-N′-tert-butyloxy carbonyl glycinamide based on WA functionality were developed for the convenient synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinoline framework. Two simple reactions, N-benzylation and addition of arylmagnesium halide on the WA functionality of the former afforded the key intermediate for convenient synthesis of N-phenylsulfonyl protected 4-aryl-1,2,3,4-tetrahydroisoquinoline, through reduction and acid promoted cyclization. With the latter, the addition of arylmagnesium halide on the WA functionality followed by the same protocol afforded the direct synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines in good yields. The acid promoted cyclization step enabled concomitant removal of N-Boc protection.

Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-II receptor antagonists

The present invention relates to urotensin II receptor antagonists, pharmaceutical compositions containing them and their use.

Synthesis and enantioselectivity of optically active 1- and 3-substituted 4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ols and related compounds as norepinephrine potentiators

Optically active 1,2-dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4- ols (1R,4R-3a and 1S,4S-3b, 1S,4R-4a, and 1R,4S-4b) and 2-methyl-4-phenyl- 1,2,3,4-tetrahydroisoquinolines (4S-5a and 4R-5b) were prepared in order to examine the effects of the 1-, 3-, and 4-substituents of 2-methyl-4-phenyl- 1,2,3,4-tetrahydroisoquinolin-4-ol (PI-OH) (1) on the enantioselectivity for norepinephrine (NE) potentiating activity. The conformations and absolute configurations of 3-5 were determined from their 1H-NMR and circular dichroism (CD) spectra and by single-crystal X-ray diffractometric analysis. The NE potentiating activity of the optically active 3-5 and previously prepared 3-methyl derivatives (3R,4R-6a and 3S,4S-6b) of PI-OH were tested. The results show that compounds 3, 4, and 6 had high enantioselectivity for NE potentiation: the 4R series of the enantiomers exhibited activity but not the 4S-enantiomers. The activity of the 4-desoxy compound 5 also resided exclusively in the 4S-enantiomer. These findings suggest the presence of a specific receptor for NE uptake, and the enantiomers 3a, 4a, 5a, and 6a may be antagonistic at this NE uptake receptor.

Reduction of isoquinoline and pyridine-containing heterocycles with lithium triethylborohydride (Super-Hydride)

Isoquinolines, quinoline and pyridines are effectively reduced to 1,2,3,4-tetrahydroisoquinolines, 1,2,3,4-tetrahydroquinolines and piperidines respectively with lithium triethylborohydride (Super-Hydride). The mechanism of the reduction was explored by reduction of isoquinoline and pyridine with lithium triethylborodeuteride (Super-Deuteride).

CYCLIZATION OF N-(2-AMINOBENZYL) BENZYLAMINO-1-PHENYL-1-ETHANOLS AND DEBENZYLATION OF THE RESULTING TETRAHYDROISOQUINOLINE DERIVATIVES

Debenzylation reactions of 2-(o-aminobenzyl)-4-phenyl-1,2,3,4-tetrahydroisoquinolines (3a, b) and their N-acetyl derivatives (4a, b), obtained by the cyclization of N-(2-aminobenzyl)benzylamino-1-phenyl-1-ethanols (1), were studied.

A CONVENIENT PROCEDURE FOR THE REDUCTIVE DESULPHURISATION OF THIOETHERS WITH NICKEL BORIDE

Nickel boride, conveniently prepared in situ from nickel (II) chloride hexahydrate and sodium borohydride, cleanly desulphurises thioethers in excellent yields.

Methylthio Activating Groups in the Synthesis of Isoquinolines

Methylthio activating groups have been found to improve the yields in six different isoquinoline syntheses: in four cases the improvement was from zero, in the unactivated system, to between 54 and 94percent.

Oxazolines. 2. 2-Substituted 2-Oxazolines as Synthons for N-(β-Hydroxyethyl)arylalkylamines, Intermediates in a Synthesis of 1,2,3,4-Tetrahydroisoquinolines and 2,3,4,5-Tetrahydro-1H-3-Benzazepines

2-(Arylalkyl)-2-oxazolines 4 (n = 1) and 2-aryl-2-oxazolines 4 (n = 0), the latter prepared in a novel reaction by cross-coupling aryl Grignard reagents with 2-(methylthio)-5-phenyl-2-oxazoline (10) and using palladium(II) chloride (14) as a catalyst, were reduced in a previously unreported reaction by diborane in refluxing THF to yield N-(β- hyroxyethyl)arylalkylamines 5 (n = 1,2).Amino alcohols 5 were cyclized to their respective heterocyclic derivatives 6 (n = 1,2) by treatment with H2SO4/TFA in refluxing methylene chloride.This paper disscuses how 2-substituted 2-oxazolines may be used to prepare1,2,3,4-tetrahydroisoquinolines 6 (n = 1) and 2,3,4,5-tetrahydro-1H-3-benzazepines 6 (n = 2) via amino alcohols 5.