116234-45-8

Basic information

• Product Name: 8-hydroxy-3-methyl-1-(4'-azidophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
• Synonyms: 8-hydroxy-3-methyl-1-(4'-azidophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS NO: 116234-45-8
• Molecular Weight: 294.356
• Mol File: 116234-45-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 8-hydroxy-3-methyl-1-(4'-azidophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-hydroxy-3-methyl-1-(4'-azidophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine(116234-45-8)
• EPA Substance Registry System: 8-hydroxy-3-methyl-1-(4'-azidophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine(116234-45-8)

Safety Data

• Hazardous Substances Data: 116234-45-8(Hazardous Substances Data)

Upstream product

• 55-81-2 4-Methoxyphenethylamine 
• 116234-46-9 8-methoxy-1-(4'-nitrophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 116351-49-6 α-<methyl>-4-nitrobenzyl alcohol 
• 6388-74-5 p-Nitrophenyloxirane 
• 116234-47-0 8-methoxy-3-methyl-1-(4'-nitrophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 116234-48-1 8-hydroxy-3-methyl-1-(4'-aminophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine 

Downstream Products

• 116234-50-5 5-(4-Azido-phenyl)-8-iodo-3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol 

Relevant articles and documents

Development of a high affinity and stereoselective photoaffinity label for the D-1 dopamine receptor: Synthesis and resolution of 7-[125I]iodo-8-hydroxy-3-methyl-1-(4'-azidophenyl) -2,3,4,5-tetrahydro-1H-3-benzazepine

In an earlier paper, we reported the development of (±)-7-iodo-8-hydroxy-3-methyl-1-(4'-azidophenyl)-2,3,4,5-tetrahydro- 1H-3-benzazepine (I-MAB) and its 125I analogue ([125I]I-MAB) as selective, high affinity photoaffinity labels for the D-1 dopamine receptor. In this report, we now describe the complete synthesis and resolution of I-MAB and the pharmacological characterization of the stereoisomers in canine striatal membranes. R-(+)-I-MAB showed highly specific dopamine D-1 receptor binding (K(D) = 0.28 nM) and binds selectively and stereoselectively to the D-1 receptor. These results further confirm the previous suggestion that, in the benzazepine series of DA agonists and antagonists, the activity principally resides in the R-(+) enantiomer, the S-(-) enantiomer being considerably less potent or inactive. Moreover, R-(+)-[125I]I-MAB, upon photolysis, identifies the ligand-binding subunits of the neuronal D-1 receptor, with an apparent M(r) of 74,000, 62,000, and 51,000 as assessed by autoradiography following sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Photoincorporation of R-(+)-[125I]I-MAB into these polypeptides was stereoselectively blocked by D-1 dopaminergic ligands with an appropriate pharmacologic profile for the receptor. R-(+)-[125I]I-MAB should thus prove to be a useful stereoselective photoaffinity label for the further characterization of the D-1 receptors.