73075-43-1

Basic information

• Product Name: 5-Chloro-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 5-Chloro-1,2,3,4-tetrahydroisoquinoline;C90102;Isoquinoline, 5-chloro-1,2,3,4-tetrahydro-;5-chloro-1,2,3,4-tetrahydroisoquinoline(SALTDATA: HCl)
• CAS NO: 73075-43-1
• Molecular Formula: C₉H₁₀ClN
• Molecular Weight: 167.64
• EINECS: -0
• Mol File: 73075-43-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 276 ºC
• Flash Point: 121 ºC
• Appearance: /
• Density: 1.162
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.94±0.20(Predicted)
• CAS DataBase Reference: 5-Chloro-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-1,2,3,4-tetrahydroisoquinoline(73075-43-1)
• EPA Substance Registry System: 5-Chloro-1,2,3,4-tetrahydroisoquinoline(73075-43-1)

Safety Data

• Hazardous Substances Data: 73075-43-1(Hazardous Substances Data)

Usage

General Description

5-Chloro-1,2,3,4-tetrahydroisoquinoline is a chemical compound with the molecular formula C9H10ClN. It is a chlorinated tetrahydroisoquinoline derivative and is commonly used in organic synthesis and pharmaceutical research. The compound has been studied for its potential pharmacological properties and has been found to exhibit activity as a dopamine D2 receptor agonist, making it a potential candidate for the treatment of neurological disorders such as Parkinson's disease. Additionally, 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. Overall, this compound has garnered significant interest in the scientific community for its potential therapeutic and toxicological implications.

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

Upstream product

• 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 
• 5430-45-5 5-chloro-isoquinoline 

Downstream Products

• 1394241-48-5 C₁₆H₁₄ClNO₄S 

Relevant articles and documents

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.

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