55507-14-7

Usage

Class

Isoquinolines

Psychoactive Drug

Yes

Potential Properties

Antipsychotic and anxiolytic

Studied for Treatment

Schizophrenia, anxiety, and other psychiatric and neurological disorders

Mechanism of Action

Selective antagonist of the serotonin receptor subtype 5-HT2C

Involvement in Brain Functions

Mood regulation, anxiety, and other brain functions

Current Status

Subject of research for potential therapeutic effects

Further Studies Needed

To determine safety and efficacy for clinical use

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 110339-53-2 C₁₆H₁₇NO 
• 100-52-7 benzaldehyde 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 201416-62-8 C₁₇H₁₈FNO₂ 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 910108-65-5 2-(chloroacetyl)-6,7-dimethoxy-1(4-fluorophenyl)-1,2,3,4-terahydroisoquinoline 
• 1147279-97-7 N-cyclopentyl-6,7-dimethoxy-1-(4-fluorophenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1147280-05-4 N-cyclohexyl-6,7-dimethoxy-1-(4-fluorophenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1147279-74-0 1-(4-fluorophenyl)-N-isopropyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-carboxamide 
• 1161432-38-7 6,7-dimethoxy-1-(4'-fluorophenyl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide 
• 922427-36-9 ethyl 2-[1-(4-fluorophenyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]-2-oxoacetate 
• 904913-16-2 2-ethyl-1-(4-fluoro-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline 

Relevant academic research and scientific papers

Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides

On the basis of X-ray crystallographic studies of the complex of hCA II with 4-(3,4-dihydro-1H-isoquinoline-2-carbonyl)benzenesulfonamide (3) (PDB code 4Z1J), a novel series of 4-(1-aryl-3,4-dihydro-1H-isoquinolin-2-carbonyl)benzenesulfonamides (23-33) wa

Strategies and synthetic methods directed toward the preparation of libraries of substituted isoquinolines

Strategies for the production of substituted isoquinoline libraries were developed and explored. Routes involving microwave-assisted variants of the Bischler-Napieralski or Pictet-Spengler reaction allowed for cyclization of substituted β-arylethylamine derivatives. The dihydroisoquinolines and tetrahydroisoquinolines thus generated could then be oxidized to their corresponding isoquinoline analogues. An alternate strategy, however, involving the preparation and activation of isoquinolin-1(2H)-ones is demonstrated to be a more practical, rapid, and efficient route to C1- and C4-substituted isoquinoline libraries.

Synthesis and evaluation of pharmacological profile of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides

In previous studies we identified several 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives displaying potent anticonvulsant effects in different animal models of epilepsy. With the aim to deepen the structure-activity relationships (SAR) fo

Synthesis of benzoazocines from substituted tetrahydroisoquinolines and activated alkynes in a tetrahydropyridine ring expansion

Tetrahydroisoquinolines underwent tandem piperidine ring enlargement in the presence of activated alkynes in acetonitrile or methanol, producing tetrahydrobenzo[d]azocines in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis, antibacterial activity and QSAR studies of 1,2-disubstituted-6, 7-dimethoxy-1,2,3,4-tetrahydroisoquinolines

Some new substituted-tetrahydroisoquinoline derivatives were synthesized and evaluated for their in vitro antimicrobial activities against the standard Gram positive and Gram negative strains: Staphylococcus aureus (ATCC 25923), S.:epidermidis (WHO-6), Es

Synthesis of carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7- dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as new potential PET AMPA receptor ligands

New carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7-dimethoxy-1,2,3, 4-tetrahydroisoquinoline derivatives were designed and synthesized as potential positron emission tomography AMPA (2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid) recep

Tandem enlargement of the tetrahydropyridine ring in 1-aryl-tetrahydroisoquinolines using activated alkynes-a new and effective synthesis of benzoazocines

Tetrahydroisoquinolines 3a-e underwent piperidine ring enlargement under the action of activated alkynes, giving benzoazocines 4, 5 and 7-11 in high yields.

Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives

As a follow up of our previous structure-activity relationship and molecular modeling studies, we synthesized a novel series of 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as potential non-competitive AMPA receptor antagonists. When te

Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist

N-Acetyl-1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives were designed and synthesized as potential noncompetitive AMPA receptor antagonists on the basis of molecular modeling studies. Sound-induced seizure testing showed that this class o

1-Aryl-3,4-dihydro-2(1H)-isoquinoline carbonyl chlorides

1-Aryl-3,4-dihydro-2(1H)-isoquinolinecarbonyl chlorides, useful in the preparation of the corresponding carboxamides, are described herein. The subject compounds can be prepared by reacting an 1-aryl-3,4-dihydro-2(1H)-isoquinoline with phosgene.