16620-96-5

Basic information

• Product Name: 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline; isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-
• CAS NO: 16620-96-5
• Molecular Formula: C₁₂H₁₇NO₂
• Molecular Weight: 207.2689
• Mol File: 16620-96-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 300.1°C at 760 mmHg
• Flash Point: 108.7°C
• Density: 1.061g/cm³
• Vapor Pressure: 0.00115mmHg at 25°C
• Refractive Index: 1.527
• CAS DataBase Reference: 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(16620-96-5)
• EPA Substance Registry System: 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(16620-96-5)

Safety Data

• Hazardous Substances Data: 16620-96-5(Hazardous Substances Data)

Usage

General Description

6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline is a chemical compound with the molecular formula C12H17NO2. It is a member of the isoquinoline family and contains two methoxy groups and a methyl group. 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline derivative, which means it is a cyclic structure with a nitrogen atom incorporated into the ring. It is a synthetic compound, and its exact biological or chemical properties are not well documented. However, isoquinoline derivatives have been studied for their potential biological activities, including as potential therapeutic agents for various medical conditions.

Upstream product

• 1699-51-0 laudanosine 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 100-97-0 hexamethylenetetramine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 88205-41-8 2-acetamido-6,7-dimethoxy-1-(3',4'-dimethoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolinium iodide 
• 88205-32-7 6,7-dimethoxy-1-(3',4'-dimethoxyphenyl)-2-nitroso-1,2,3,4-tetrahydroisoquinoline 
• 2246-26-6 1,2-dihydro-2-methylpapaverine 
• 5884-67-3 armepavine 

Downstream Products

• 37491-98-8 N-methyl-norsalsolinol 
• 57553-18-1 2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide salt 
• 4008-69-9 6,7-dimethoxy-2-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 22329-48-2 1-(3,4-dimethoxyphenyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 22324-83-0 6,7-dimethoxy-1-(3,4,5-trimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 32407-75-3 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 20012-08-2 1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydro-3H-benzazepine 
• 1356845-32-3 1-((4-chlorophenyl)ethynyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 490-53-9 (+/-)-carnegine 
• 5630-11-5 (+/-)-glaucine 
• 1699-51-0 laudanosine 
• 20412-85-5 2-benzyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 70319-15-2 (±)-6,7-dimethoxy-1-(4-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydroisoquinoline 
• 180003-15-0 metofoline 

Relevant articles and documents

Engineering Orthogonal Methyltransferases to Create Alternative Bioalkylation Pathways

S-adenosyl-l-methionine (SAM)-dependent methyltransferases (MTs) catalyse the methylation of a vast array of small metabolites and biomacromolecules. Recently, rare carboxymethylation pathways have been discovered, including carboxymethyltransferase enzymes that utilise a carboxy-SAM (cxSAM) cofactor generated from SAM by a cxSAM synthase (CmoA). We show how MT enzymes can utilise cxSAM to catalyse carboxymethylation of tetrahydroisoquinoline (THIQ) and catechol substrates. Site-directed mutagenesis was used to create orthogonal MTs possessing improved catalytic activity and selectivity for cxSAM, with subsequent coupling to CmoA resulting in more efficient and selective carboxymethylation. An enzymatic approach was also developed to generate a previously undescribed co-factor, carboxy-S-adenosyl-l-ethionine (cxSAE), thereby enabling the stereoselective transfer of a chiral 1-carboxyethyl group to the substrate.

Synthesis of phthalideisoquinoline and protoberberine alkaloids and indolo[2,1-α]isoquinolines in a divergent route involving palladium(0)- catalyzed carbonylation

6,7,3',4'-Alkoxy-substituted 1-(2'-bromobenzoyl)-3,4-dihydroisoquinoline methiodides 17 were treated with sodium borohydride in methanol or acetic acid to give erythro-1-(2'-bromo-α-hydroxybenzyl)-2-methyl-1,2,3,4- tetrahydroisoquinolines 19. Treatment of 17 with lithium aluminum hydride in tetrahydrofuran gave the threo-isomer 20 in preference to the erythro 19. On the basis of studies on palladium(0)-catalyzed carbonylation of 2-bromo-3,4- dimethoxybenzyl alcohol to 6,7-dimethoxyphthalide, amino alcohol 19 or 20 was treated with a catalytic amount of palladium(II) acetate and triphenylphosphine in an atmosphere of carbon monoxide in the presence of chlorotrimethylsilane and potassium carbonate in boiling toluene to give the corresponding erythro- or threo-types of phthalideisoquinoline alkaloids 1 or 2, respectively. One-pot cyclization of the erythro-amino alcohols 19 was achieved by heating in N,N-dimethylformamide containing potassium carbonate to give 2,3,8,9- or 2,3,9,10-alkoxy-substituted 5,6-dihydroindolo[2,1- α]isoquinolines 3, which have a unique tetracyclic skeleton characteristic of dibenzopyrrocoline alkaloids. Similarly, palladium-(0)-catalyzed carbonylation of 1-(2'-bromobenzyl)tetrahydroisoquinolines 21 in the presence of excess potassium carbonate was found to give 8-oxoberbines 22, which on reduction with lithium aluminum hydride can be converted to protoberberine alkaloids 4.

BIOMIMETIC OXIDATIONS OF BENZYLISOQUINOLINE ALKALOUDS. I. THE PEROXIDASE AND ASCORBIC OXIDASE-CATALYSED OXIDATION

The enzyme peroxidase behaves as a mixed-function oxidase toward the benzylisoquinoline alkaloid nucleus, giving rise to various phenoxy radicals depending on the substrate.These give either C(4) hydroxylation or C(5') hydroxylation and cyclisation to an aporphine, or cleavage of the C(1)-C(9) bond.