145554-63-8

Basic information

• Product Name: 3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)
• Synonyms: 3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)
• CAS NO: 145554-63-8
• Molecular Formula: C9H12N2
• Molecular Weight: 148.21
• Product Categories: AMINEPRIMARY
• Mol File: 145554-63-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)(145554-63-8)
• EPA Substance Registry System: 3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)(145554-63-8)

Safety Data

• Hazardous Substances Data: 145554-63-8(Hazardous Substances Data)

Upstream product

• 580-17-6 3-aminoquinoline 
• 673-06-3 D-(R)-phenylalanine 
• 2448-45-5 Cbz-D-Phe 
• 121989-61-5 (R)-3-amino-1-methoxy-3,4-dihydroquinolin-2(1H)-one 
• 169383-17-9 (2R)-2-amino-3-(2-nitrophenyl)propanoic acid 
• 40615-17-6 (3S)-3-amino-3,4-dihydro-1H-quinolin-2-one 
• 1991-82-8 (2S)-2-amino-3-(2-nitrophenyl)propanoic acid 

Downstream Products

• 1609340-85-3 rac-8-[(2,6-difluorobenzyl)oxy]-2-methyl-N-(1,2,3,4-tetrahydroquinolin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide 
• 132875-37-7 (5R)-5-amino-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-1(2H)-one 
• 152886-85-6 U 91356 

Relevant articles and documents

2,3-Dihydro and Carbocyclic Analogues of Tryptamines: Interaction with Serotonin Receptors

Several dihydro and carbocyclic analogues of tryptamine were evaluated in order to determine the role of the heterocyclic portion of the indole nucleus on the interaction of indolealkylamines with the serotonin receptors of the rat fundus.Reduction of the C2-C3 double bond or replacement of the indole nitrogen with sp3-hybridized carbon atom results in a 50percent decrease in receptor affinity.Complete removal of the five-membered ring of N,N-dimethyltryptamine reduces affinity by an order of magnitude.It appears that an intact indole nucleus, though not entirely necessary, results in an optimal receptor interaction for the indolealkylamines examined.

INDOLE AHR INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

Novel Analogues of (R)-5-(Methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (Sumanirole) Provide Clues to Dopamine D2/D3 Receptor Agonist Selectivity

Novel 1-, 5-, and 8-substituted analogues of sumanirole (1), a dopamine D2/D3 receptor (D2R/D3R) agonist, were synthesized. Binding affinities at both D2R and D3R were higher when determined in competition with the agonist radioligand [3H]7-hydroxy-N,N-dipropyl-2-aminotetralin (7-OH-DPAT) than with the antagonist radioligand [3H]N-methylspiperone. Although 1 was confirmed as a D2R-preferential agonist, its selectivity in binding and functional studies was lower than previously reported. All analogues were determined to be D2R/D3R agonists in both GoBRET and mitogenesis functional assays. Loss of efficacy was detected for the N-1-substituted analogues at D3R. In contrast, the N-5-alkyl-substituted analogues, and notably the n-butyl-arylamides (22b and 22c), all showed improved affinity at D2R over 1 with neither a loss of efficacy nor an increase in selectivity. Computational modeling provided a structural basis for the D2R selectivity of 1, illustrating how subtle differences in the highly homologous orthosteric binding site (OBS) differentially affect D2R/D3R affinity and functional efficacy.