801167-08-8

Basic information

• Product Name: [2-(quinolin-8-yloxy)ethyl]amine dihydrochloride
• Synonyms: 2-(quinolin-8-yloxy)ethanamine;2-(8-Quinolinyloxy)ethanamine dihydrochloride;2-(8-Quinolinyloxy)-1-ethanamine;[2-(quinolin-8-yloxy)ethyl]amine dihydrochloride
• CAS NO: 801167-08-8
• Molecular Formula: C11H14Cl2N2O
• Molecular Weight: 261.14766
• Mol File: 801167-08-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [2-(quinolin-8-yloxy)ethyl]amine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: [2-(quinolin-8-yloxy)ethyl]amine dihydrochloride(801167-08-8)
• EPA Substance Registry System: [2-(quinolin-8-yloxy)ethyl]amine dihydrochloride(801167-08-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 801167-08-8(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
[2-(quinolin-8-yloxy)ethyl]amine dihydrochloride is used as a ligand in coordination chemistry for its ability to form stable complexes with metal ions. This application is significant due to the compound's potential role in enhancing the properties of metal complexes, such as stability, reactivity, and selectivity.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, [2-(quinolin-8-yloxy)ethyl]amine dihydrochloride is used as a precursor in the synthesis of other organic compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, making it a crucial component in the advancement of pharmaceutical research and drug discovery.
Used in Research and Development:
[2-(quinolin-8-yloxy)ethyl]amine dihydrochloride is also employed in research and development settings, where its properties are explored for potential applications in various fields. [2-(quinolin-8-yloxy)ethyl]amine dihydrochloride's versatility and unique structure make it an attractive candidate for further study and the creation of novel materials and compounds with diverse applications.

Upstream product

• 148-24-3 8-quinolinol 

Relevant articles and documents

Discovery of Novel pERK1/2- or β-Arrestin-Preferring 5-HT1AReceptor-Biased Agonists: Diversified Therapeutic-like versus Side Effect Profile

Novel 1-(1-benzoylpiperidin-4-yl)methanamine derivatives with high affinity and selectivity for serotonin 5-HT1A receptors were obtained and tested in four functional assays: ERK1/2 phosphorylation, adenylyl cyclase inhibition, calcium mobilization, and β-arrestin recruitment. Compounds 44 and 56 (2-methylaminophenoxyethyl and 2-(1H-indol-4-yloxy)ethyl derivatives, respectively) were selected as biased agonists with highly differential "signaling fingerprints"that translated into distinct in vivo profiles. In vitro, 44 showed biased agonism for ERK1/2 phosphorylation and, in vivo, it preferentially exerted an antidepressant-like effect in the Porsolt forced swimming test in rats. In contrast, compound 56 exhibited a first-in-class profile: it preferentially and potently activated β-arrestin recruitment in vitro and potently elicited lower lip retraction in vivo, a component of "serotonergic syndrome". Both compounds showed promising developability properties. The presented 5-HT1A receptor-biased agonists, preferentially targeting various signaling pathways, have the potential to become drug candidates for distinct central nervous system pathologies and possessing accentuated therapeutic activity and reduced side effects.

Novel hits for acetylcholinesterase inhibition derived by docking-based screening on ZINC database

The inhibition of the enzyme acetylcholinesterase (AChE) increases the levels of the neurotransmitter acetylcholine and symptomatically improves the affected cognitive function. In the present study, we searched for novel AChE inhibitors by docking-based virtual screening of the standard lead-like set of ZINC database containing more than 6 million small molecules using GOLD software. The top 10 best-scored hits were tested in vitro for AChE affinity, neurotoxicity, GIT and BBB permeability. The main pharmacokinetic parameters like volume of distribution, free fraction in plasma, total clearance, and half-life were predicted by previously derived models. Nine of the compounds bind to the enzyme with affinities from 0.517 to 0.735 μM, eight of them are non-toxic. All hits permeate GIT and BBB and bind extensively to plasma proteins. Most of them are low-clearance compounds. In total, seven of the 10 hits are promising for further lead optimisation. These are structures with ZINC IDs: 00220177, 44455618, 66142300, 71804814, 72065926, 96007907, and 97159977.

New serotonin 5-HT1A receptor agonists endowed with antinociceptive activity in vivo

We report the synthesis of new compounds 4-35 based on two different openings (A and B) of the chromane ring present in the previously identified 5-HT1A receptor (5-HT1AR) ligand 3. The synthesized compounds were assessed for binding affinity, selectivity, and functional activity at the 5-HT1AR. Selected candidates resulting from B opening were also evaluated for their potential antinociceptive effect in vivo and pharmacokinetic properties in vitro. Analogue 19 [2-(4-{[2-(2-ethoxyphenoxy) ethyl]amino}butyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione] has been characterized as a high-affinity and potent 5-HT1AR agonist (K i = 2.3 nM; EC50 = 19 nM). Pharmacokinetic studies indicated that compound 19 displays a good metabolic stability in human liver microsomes (t1/2 ～ 3 h and CLint = 3.5 mL/min/kg, at 5 μM), and a low level of protein binding (25%, at 5 μM). Interestingly, 19 (3 mg/kg, ip, and 30 mg/kg, po) caused significant attenuation of formalin-induced behavior in early and late phases of the mouse intradermal formalin test of pain, and this in vivo effect was reversed by the selective 5-HT1AR antagonist WAY-100635. Thus, the new 5-HT1AR agonist identified in this work, 19, exhibits oral analgesic activity, and the results herein represent a step toward identifying new therapeutics for the control of pain.