74115-01-8

Basic information

• Product Name: (+/-)-chloro-APB
• Synonyms: (+/-)-chloro-APB;1H-3-Benzazepine-7,8-diol,6-chloro-2,3,4,5-tetrahydro-1-phenyl-3-(2-propen-1-yl)-, hydrobromide (1:1)
• CAS NO: 74115-01-8
• Molecular Formula: BrH*C₁₉H₂₀ClNO₂
• Molecular Weight: 410.73254
• Mol File: 74115-01-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 203-204 °C(Solv: isopropanol (67-63-0); ethyl ether (60-29-7))
• Appearance: /
• CAS DataBase Reference: (+/-)-chloro-APB(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-chloro-APB(74115-01-8)
• EPA Substance Registry System: (+/-)-chloro-APB(74115-01-8)

Safety Data

• Hazardous Substances Data: 74115-01-8(Hazardous Substances Data)

Usage

Description

(+/-)-chloro-APB is a chemical compound that acts as a dopamine (D1) agonist and modulates GABAB inhibitory post-synaptic potentials (IPSPs) in the ventral tegmental area of brain slices.

Uses

Used in Pharmaceutical Industry:
(+/-)-chloro-APB is used as a research tool for studying the effects of dopamine (D1) agonism and GABAB inhibitory post-synaptic potentials (IPSPs) modulation on various neurological and psychiatric disorders. Its ability to modulate these pathways makes it a valuable compound for understanding the underlying mechanisms of these conditions and potentially developing novel therapeutic approaches.
Used in Neuroscience Research:
(+/-)-chloro-APB is used as a research compound in neuroscience to investigate the role of dopamine (D1) receptors and GABAB receptors in the brain's reward and motivation systems. This knowledge can contribute to the development of new treatments for addiction, depression, and other related disorders.

Hazard

A poison.

Upstream product

• 74115-02-9 3-allyl-6-chloro-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 
• 20569-49-7 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 67287-38-1 6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 67287-46-1 6-chloro-7,8-dimethoxy-3-cyano-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 
• 104113-80-6 6-bromo-7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 67287-40-5 6-bromo-7,8-dimethoxy-2,3,4,5-tetrahydro-1-phenyl-1H-3-benzazepine hydrobromide 
• 264-54-0 1H-benzo[b]azepine 
• 106-95-6 allyl bromide 

Downstream Products

• 80751-66-2 Acetic acid 8-acetoxy-3-allyl-9-chloro-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl ester 

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-3-LOWER ALKYL-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINES

6-Halo-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines whose structures have a lower alkyl substituted at the 3 or N-position have potent and often specific anti-Parkinsonism activity by means of their central dopaminergic effect. The lead compound of the series is 6-chloro-3-methyl-1-phenyl-7,8-dihydroxy-2,3,4,5-tetrahydro-1H-3-benzazepin e as the base or its salts such as the hydrochloride, hydrobromide or methane sulfonate.