73075-43-1

Usage

Uses

Used in Pharmaceutical Research:
5-Chloro-1,2,3,4-tetrahydroisoquinoline is used as a research compound for its potential pharmacological properties. It has been found to exhibit activity as a dopamine D2 receptor agonist, making it a promising candidate for the treatment of neurological disorders such as Parkinson's disease.
Used in Organic Synthesis:
In the field of organic synthesis, 5-Chloro-1,2,3,4-tetrahydroisoquinoline is utilized as a key intermediate in the synthesis of various organic compounds and pharmaceuticals. Its unique structure and reactivity make it a valuable building block for the development of new molecules with potential therapeutic applications.
Used in Neurodegenerative Disease Research:
5-Chloro-1,2,3,4-tetrahydroisoquinoline has also been investigated for its potential role in the formation of neurotoxic metabolites, which may contribute to the development of neurodegenerative diseases. Its study in this context helps researchers understand the underlying mechanisms of these diseases and explore potential therapeutic interventions.
Overall, 5-Chloro-1,2,3,4-tetrahydroisoquinoline has garnered significant interest in the scientific community for its potential therapeutic and toxicological implications, making it a valuable compound in various applications across the pharmaceutical and chemical industries.

InChI:InChI=1/C9H10ClN/c10-9-3-1-2-7-6-11-5-4-8(7)9/h1-3,11H,4-6H2

Upstream product

• 5430-45-5 5-chloro-isoquinoline 
• 129075-59-8 5-chloro-3,4-dihydro-2H-isoquinolin-1-one 
• 1365759-61-0 [2-(2-chloro-phenyl)-ethyl]-carbamic acid ethyl ester 
• 105871-20-3 N-acetyl-2-(2-chlorophenyl)ethylamine 
• 89-98-5 2-chloro-benzaldehyde 
• 13078-80-3 2-(2-chlorophenyl)ethanamine 
• 937591-81-6 2-acetyl-5-chloro-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 1394241-48-5 C₁₆H₁₄ClNO₄S 

Relevant academic research and scientific papers

Easy Access to 2,4-Disubstituted Cyclopentenones by a Gold(III)-Catalyzed A3-Coupling/Cyclization Cascade

An efficient and convenient synthesis of 2,4-disubstituted cyclopentenones has been achieved through a Au(III)-catalyzed isomerization-A3-coupling/cyclization cascade. A possible mechanism involving an initial Au(III)-catalyzed isomerization, A3-type coupling, and cyclization via an enol intermediate is postulated.

Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine

An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between commercially available anthranils and cyclic amines is described. The developed transformation proceeds with the merits of high step- and atom-efficiency, a broad substrate scope, and good to excellent yields, without additional catalysts, and offers a practical way for the preparation of rutaecarpine and its derivatives with structural diversity.

The influence of substitution at aromatic part of 1,2,3,4-tetrahydroisoquinoline on in vitro and in vivo 5-HT1A/5-HT2A receptor activities of its 1-adamantoyloaminoalkyl derivatives

Further structure-activity relationship (SAR) studies with the 1,2,3,4-tetrahydroisoquinoline (THIQ) class of 5-HT1A ligands led to the synthesis of new 1-adamantoyloaminoalkyl derivatives. The impact of substituent variations in the aromatic part of THIQ moiety on 5-HT1A and 5-HT2A receptor affinities, as well as in vivo functional properties of the investigated compounds were discussed. It was found that modification reduced the binding affinity for 5-HT1A receptors (in comparison with unsubstituted THIQ derivatives); however, the majority of new compounds still remained potent 5-HT1A ligands (Ki = 4.9-46 nM) and most of them showed features of partial agonists of postsynaptic 5-HT1A receptors. At the same time, their 5-HT2A receptor affinity was slightly increased (Ki = 40-1475 nM), which resulted in a loss of 5-HT2A/5-HT1A selectivity. 5-Br,8-OCH3 derivative - the most potent, mixed 5-HT1A/5-HT2A ligand - produced activation of presynaptic 5-HT1A receptors and showed properties of a 5-HT2A receptor antagonist. Copyright

Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis: I. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines

In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2>6,7,8-Cl3>7-Cl~8-Cl>5,6,7,8-Cl4>5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.