67287-39-2

Basic information

• Product Name: R(+)-6-CHLORO-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROBROMIDE
• Synonyms: R(+)-6-CHLORO-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROBROMIDE;R(+)-SKF-81297 HYDROBROMIDE;(R)-6-Chloro-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol hydrobromide;9-chloro-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol:hydrobromide
• CAS NO: 67287-39-2
• Molecular Formula: BrH*C₁₆H₁₆ClNO₂
• Molecular Weight: 370.67
• Mol File: 67287-39-2.mol
• Article Data: 5

Chemical Properties

• Appearance: white to off-white/solid
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: H2O: 6 mg/mL
• CAS DataBase Reference: R(+)-6-CHLORO-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROBROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: R(+)-6-CHLORO-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROBROMIDE(67287-39-2)
• EPA Substance Registry System: R(+)-6-CHLORO-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROBROMIDE(67287-39-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 67287-39-2(Hazardous Substances Data)

Usage

Uses

SKF 81297C is a dopamine D1 agonist (1).

Hazard

A poison.

Biological Activity

skf 81297 hydrobromide is a selective agonist of the dopamine d1-like receptor, with a ki value of 1.9 nm. the dopamine d1-like receptors, consisting of d1 and d5 subtypes, are a subfamily of dopamine receptors that mediate excitatory neurotransmission after binding the endogenous neurotransmitter dopamine. the dopamine d1-like receptors have been implicated in dopaminergic regulation of a variety of fundamental neurophysiologic processes including mood, motivation, cognitive function, as well as motor activity.1. neumeyer jl, kula ns, bergman j, baldessarini rj. receptor affinities of dopamine d1 receptor-selective novel phenylbenzazepines. european journal of pharmacology, 2003, 474(2-3): 137-140.2. undieh as. pharmacology of signaling induced by dopamine d(1)-like receptor activation. pharmacology & therapeutics, 2010, 128(1): 37-60.3. vermeulen rj, drukarch b, sahadat mc, et al. the dopamine d1 agonist skf 81297 and the dopamine d2 agonist ly 171555 act synergistically to stimulate motor behavior of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-lesioned parkinsonian rhesus monkeys. movement disorders, 1994, 9(6): 664-672.

Upstream product

• 67287-46-1 6-chloro-7,8-dimethoxy-3-cyano-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 20569-49-7 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 20011-97-6 N-[2-(3,4-dimethoxyphenyl)ethyl]-2-phenyl-2-hydroxyethylamine 
• 93983-13-2 2-chloro-3,4-dimethoxybenzyl alcohol 
• 7537-07-7 2-(2-chloro-3,4-dimethoxyphenyl)acetonitrile 
• 67287-36-9 2-(2-chloro-3,4-dimethoxyphenyl)ethylamine 
• 37687-57-3 2-chloro-3-hydroxy-4-methoxybenzaldehyde 
• 5417-17-4 2-chloro-3,4-dimethoxybenzaldehyde 
• 93983-14-3 2-chloro-3,4-dimethoxybenzyl chloride 
• 67287-37-0 N-(2-Hydroxy-2-phenethyl)-N-<2-(2'-chlor-3',4'-dimethoxyphenyl)-ethyl>-amin 
• 621-59-0 isovanillin 
• 67287-38-1 6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 104113-80-6 6-bromo-7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 67287-58-5 6-chloro-7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 

Downstream Products

• 80751-70-8 6-Chloro-1-phenyl-3-(4-trifluoromethyl-benzyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol 
• 80751-69-5 6-chloro-7,8-dihydroxy-3-(4-methoxybenzyl)-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 67287-70-1 6-chloro-7,8-dihydroxy-3-(4-methoxybenzoyl)-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 67287-68-7 6-chloro-7,8-dihydroxy-1-phenyl-3-(p-trifluoromethylbenzoyl)-2,3,4,5-tetrahydro-1H-3-benzazepine 

Relevant articles and documents

(+/-)-3-Allyl-6-bromo-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin, a New High-Affinity D1 Dopamine Receptor Ligand: Synthesis and Structure-Activity Relationship

The 7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines form a series of compounds having a high affinity at the D1 dopamine receptor.The 6-chloro derivative has been previously shown to have enhanced affinity, selectivity, and agonist activity.In an attempt to study the effect of substitution of a 6-bromo group in place of the 6-chloro, we hawe synthesized a series of compounds and evaluaed them for their affinity for the D1 receptor.The results show that the 6-bromo derivatives have virtually identical affinities to their 6-chloro counterparts, a findingsimilar to that found in the D1 antagonist 7-halo-8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine series.From the present work, 3-allyl-6-bromo-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (6-Br-APB) has been identified as a suitable candidate for further in vivo studies and resolution into its active and inactive enantiomers.

6-HALO-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINES

7,8-Dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines having a halo substituent at the 6-position have potent dopaminergic activity. The 6-chloro congeners are most active.

2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE-7,8-DIONES

Novel benzazepine derivatives having central and peripheral dopaminergic activity useful in treating Parkinson's and cardiovascular diseases. The compounds have additional use as intermediates for the synthesis of other benzazepines with similar useful properties. The 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-dione derivatives are particularly useful.