115514-80-2

Basic information

• Product Name: 7-chloro-6-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 7-chloro-6-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 115514-80-2
• Molecular Weight: 259.735
• Mol File: 115514-80-2.mol

Chemical Properties

• CAS DataBase Reference: 7-chloro-6-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-6-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinoline(115514-80-2)
• EPA Substance Registry System: 7-chloro-6-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinoline(115514-80-2)

Safety Data

• Hazardous Substances Data: 115514-80-2(Hazardous Substances Data)

Upstream product

• 96-09-3 styrene oxide 
• 115514-78-8 N-(3-chloro-4-methoxybenzyl)-2-hydroxyphenethylamine 
• 2393-23-9 4-methoxy-benzylamine 
• 115514-77-7 (3-chloro-4-methoxyphenyl)methanamine 
• 115514-79-9 7-chloro-6-methoxy-4-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Synthesis and pharmacological characterization of 1-phenyl-, 4-phenyl-, and 1-benzyl-1,2,3,4-tetrahydroisoquinolines as dopamine receptor ligands

A series of 1-phenyl-, 4-phenyl-, and 1-benzyl-1,2,3,4-tetrahydroisoquinolines have been prepared as ring-contracted analogues of the prototypical D1 dopamine receptor antagonist SCH23390 [(R)-(+)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3 benzazepine]. The affinity and selectivity of these isoquinolines for D1 receptors was determined by three biochemical endpoints in membrane homogenates prepared from rat corpus striatum: the potency to compete for [3H]SCH23390 binding sites; the potency to compete for [3H]spiperone (a D2 receptor ligand) binding sites; and effects on dopamine-stimulated adenylate cyclase. Competitive binding measurements at D1 sites showed SCH23390 to possess the highest affinity, followed by 1-phenyl > 1-benzyl > 4-phenyl for the isoquinolines. These results were highly correlated with the ability of the test compounds to antagonize dopamine-stimulated adenylate cyclase (r = 0.98). None of the compounds alone stimulated cAMP formation at concentrations of 10 nM to 100 μM. D2 competition binding showed the 1-benzyl derivative to possess the highest affinity, followed by 4-phenyl > SCH23390 > 1-phenyl. The tertiary 1-phenyl derivative was more potent than the secondary 1-phenyl analogue in all assays. Interestingly, resolution and single-crystal X-ray analysis of the tertiary N-methyl-1-phenyltetrahydroisoquinoline showed the most active enantiomer to possess the S absolute configuration, in contrast to the benzazepine (R)-SCH23390.