109250-11-5

Basic information

• Product Name: 1-(3-hydroxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 1-(3-hydroxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 109250-11-5
• Molecular Weight: 299.37
• Mol File: 109250-11-5.mol

Chemical Properties

• CAS DataBase Reference: 1-(3-hydroxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-hydroxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(109250-11-5)
• EPA Substance Registry System: 1-(3-hydroxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(109250-11-5)

Safety Data

• Hazardous Substances Data: 109250-11-5(Hazardous Substances Data)

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 142741-11-5 N-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-(3-hydroxy-phenyl)-acetamide 
• 59756-83-1 2-(3-(benzyloxy)phenyl)acetyl chloride 
• 2348-02-9 2-(3-benzyloxyphenyl)-N-(3,4-dimethoxyphenethyl)acetamide 
• 1860-58-8 3-benzyloxyphenylacetic acid 
• 621-37-4 m-hydroxyphenylacetic acid 
• 1834-15-7 1-(3-benzyloxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline; hydrochloride 
• 142741-12-6 1-(3-benzyloxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 109808-84-6 1-(3-methoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Effect of 1-Substitution on Tetrahydroisoquinolines as Selective Antagonists for the Orexin-1 Receptor

Selective blockade of the orexin-1 receptor (OX1) has been suggested as a potential approach to drug addiction therapy because of its role in modulating the brain's reward system. We have recently reported a series of tetrahydroisoquinoline-based OX1 selective antagonists. Aimed at elucidating structure-activity relationship requirements in other regions of the molecule and further enhancing OX1 potency and selectivity, we have designed and synthesized a series of analogues bearing a variety of substituents at the 1-position of the tetrahydroisoquinoline. The results show that an optimally substituted benzyl group is required for activity at the OX1 receptor. Several compounds with improved potency and/or selectivity have been identified. When combined with structural modifications that were previously found to improve selectivity, we have identified compound 73 (RTIOX-251) with an apparent dissociation constant (Ke) of 16.1 nM at the OX1 receptor and >620-fold selectivity over the OX2 receptor. In vivo, compound 73 was shown to block the development of locomotor sensitization to cocaine in rats. (Chemical Equation Presented).

Enantioselective Oxidative Aerobic Dealkylation of N-Ethyl Benzylisoquinolines by Employing the Berberine Bridge Enzyme

N-Dealkylation methods are well described for organic chemistry and the reaction is known in nature and drug metabolism; however, to our knowledge, enantioselective N-dealkylation has not been yet reported. In this study, exclusively the (S)-enantiomers o

Biocatalytic enantioselective oxidative C-C coupling by aerobic C-H activation

Bridging the gap: The berberine bridge enzyme (BBE) was employed for the first preparative oxidative biocatalytic C-C coupling that leads to a new intramolecular bond. This unique transformation requires O2 as sole stoichiometric oxidant and gives access to novel optically pure (S)-berbine 2 and (R)-1-benzyl-1,2,3,4-tetrahydroisoquinoline 1 alkaloid derivatives by kinetic resolution.