5825-45-6

Basic information

• Product Name: 1-Amino-1,2,3,4-tetrahydroquinoline
• Synonyms: 1,2,3,4-tetrahydro-quinolin-1-amine;1-Amino-1,2,3,4-Tetrahydro Quinolinoe;3,4-dihydro-2H-quinolin-1-amine;N-Amino-1,2,3,4-tetrahydroquinoline;1-amino-1,2,3,4-tetrahydroQUINOLINE:3,4-dihydro-1(2h)-quinolinamine;1-Amino-1,2,3,4-tetrahydroquinoline;3,4-DIHYDRO-2H-QUINOLIN-1-YLAMINE;3,4-DIHYDRO-1(2H)-QUINOLINAMINE
• CAS NO: 5825-45-6
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.2
• Mol File: 5825-45-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: 55 °C
• Boiling Point: 274.3°C at 760 mmHg
• Flash Point: 148.3°C
• Appearance: /
• Density: 1.098g/cm³
• Vapor Pressure: 0.00543mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 5.24±0.20(Predicted)
• CAS DataBase Reference: 1-Amino-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Amino-1,2,3,4-tetrahydroquinoline(5825-45-6)
• EPA Substance Registry System: 1-Amino-1,2,3,4-tetrahydroquinoline(5825-45-6)

Safety Data

• Hazardous Substances Data: 5825-45-6(Hazardous Substances Data)

Usage

General Description

1-Amino-1,2,3,4-tetrahydroquinoline is an organic compound classified under the tetrahydroquinoline group, featuring an aromatic ring fused to a piperidine ring. This chemical, which has the molecular formula C9H12N2, holds relevance in the field of pharmaceuticals as it forms part of the structure of various bioactive molecules and medicinal drugs. Proposed use cases for this compound include Alzheimer's treatments and antidepressants, given its potential inhibitory effects on several types of brain receptors. However, as with many chemical substances, handling requires careful safety measures due to its potential hazardous characteristics.

InChI:InChI=1/C9H12N2/c10-11-7-3-5-8-4-1-2-6-9(8)11/h1-2,4,6H,3,5,7,10H2

Upstream product

• 5825-44-5 N-nitroso-1,2,3,4-tetrahydroquinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 2739-17-5 1,2,3,4-tetrahydroquinoline hydrochloride 

Downstream Products

• 87866-74-8 benzophenone 1,2,3,4-tetrahydroquinolin-1-ylhydrazone 
• 18502-95-9 4-chloro-N-(3,4-dihydro-2H-quinolin-1-yl)-3-sulfamoyl-benzamide 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 80545-12-6 N-(3,4-Dihydro-2H-quinolin-1-yl)-guanidine; compound with nitric acid 
• 4501-08-0 6-phenyl-1,2,3,4-tetrahydroquinoline 
• 60640-18-8 8-phenyl-1,2,3,4-tetrahydro-quinoline 
• 33131-92-9 1-(2-Aminoethyl)-5,6-dihydro-2-methyl-4H-pyrrolo<3.2.1-i,j>chinolin 
• 40619-71-4 2-(2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-6-yl)ethylamine 

Relevant articles and documents

Structure - Antitussive activity relationships of naltrindole derivatives. Identification of novel and potent antitussive agents

We have previously reported antitussive effects of naltrindole (NTI), a typical δ opioid receptor antagonist, in a rat model. The ED50 values of NTI by intraperitoneal and peroral injections were 104 μg/kg and 1840 μg/kg, respectively, comparable to those of codeine. Codeine, one of the most reliable centrally acting antitussive drugs, has μ agonist activity and thus the same side effects as morphine, e.g., constipation, dependency, and respiratory depression. Because NTI is a δ opioid antagonist, its derivatives have potential as highly potent antitussives, free from the μ opioid agonist side effects. We attempted to optimize the NTI derivatives to develop novel antitussive agents. On the basis of the studies of structure - antitussive activity relationships of alkyl substituted NTI derivatives, we designed NTI derivatives with extra ring fused structures. As a clinical candidate, we identified a highly potent new compound, (5R,9R,13S,14S)-17- cyclopropylmethyl-6,7-didehydro-4,5-epoxy-5′,6′-dihydro-3-methoxy- 4′H-pyrrolo[3,2,1-ij]quinolino[2′,1′:6,7]morphinan-14-ol (5b) methanesulfonate (TRK-850) which was effective even by oral administration (ED50 6.40 μg/kg).

Selective reduction of N-nitroso aza-aliphatic cyclic compounds to the corresponding N-amino products using zinc dust in CO2–H2O medium

[Figure not available: see fulltext.] A new method for reduction of N-nitroso aza-aliphatic cyclic compounds employing zinc in pressurized CO2–H2O medium has been developed. H2O and NH4Cl were used as hydrogen donors, and reduction was performed under environmentally benign conditions. The presented approach allowed to obtain the respective N-amino products selectively and in excellent yields (up to 97%).

A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles

A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.