4118-36-9

Basic information

• Product Name: 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 6,7-DIMETHOXY-1-PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE;1,2,3,4-tetrahydro-6,7-diMethoxy-1-phenylisoquinoline
• CAS NO: 4118-36-9
• Molecular Formula: C₁₇H₁₉NO₂
• Molecular Weight: 269.34
• EINECS: 258-913-7
• Mol File: 4118-36-9.mol

Chemical Properties

• Melting Point: 127-128℃
• Boiling Point: 400.9°Cat760mmHg
• Flash Point: 167.1°C
• Appearance: /
• Density: 1.101
• Vapor Pressure: 1.23E-06mmHg at 25°C
• Refractive Index: 1.564
• PKA: 8.26±0.40(Predicted)
• CAS DataBase Reference: 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline(4118-36-9)
• EPA Substance Registry System: 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline(4118-36-9)

Safety Data

• Hazardous Substances Data: 4118-36-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline is used as a neuroprotective agent for its potential to protect neurons from damage, which is crucial in the treatment of neurodegenerative diseases. Its neuroprotective properties are attributed to its ability to modulate cellular pathways and provide a supportive environment for neuronal health.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline is used as a lead compound for the development of new drugs targeting neurodegenerative conditions. Its structure and properties allow for the exploration of its potential in modulating dopamine receptor activity, which is significant in the treatment of diseases like Parkinson's.
Used in Pain Management Applications:
6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline is utilized as an analgesic agent due to its capacity to alleviate pain. Its effectiveness in pain management could be beneficial in the development of new pain relief medications, offering an alternative or adjunct to existing therapies.
Used in Dopamine Receptor Modulation:
As a dopamine receptor agonist, 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline is applied in the research and development of treatments for conditions affected by dopamine imbalances, such as Parkinson's disease. Its agonistic activity on dopamine receptors may help in managing motor symptoms and other related impairments.

InChI:InChI=1/C17H19NO2/c1-19-15-10-13-8-9-18-17(12-6-4-3-5-7-12)14(13)11-16(15)20-2/h3-7,10-11,17-18H,8-9H2,1-2H3

Upstream product

• 75767-96-3 N-benzylidene-β-(2-bromo-4,5-dimethoxyphenyl)ethylamin 
• 100-52-7 benzaldehyde 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 20515-61-1 2-phenyl-4,4-dimethyloxazolidine 
• 10133-74-1 N-benzylidene-2-(3',4'-dimethoxyphenyl)ethylamine 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 591-51-5 phenyllithium 
• 67616-16-4 N-[2-(3,4-dimethoxyphenyl)ethyl]benzamide 
• 98-88-4 benzoyl chloride 
• 63375-81-5 2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine 
• 10133-74-1 N-phenylmethylene-2-(3,4-dimethoxyphenyl)ethylamine 
• 618-31-5 benzylidene dibromide 
• 136905-00-5 (S)-(-)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 24456-59-5 6,7-dimethoxy-3,4-dihydroisoquinoline-1(2H)-thione 

Downstream Products

• 83407-60-7 1-Phenyl-2-(3-bromopropyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 4008-69-9 6,7-dimethoxy-2-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 10172-51-7 6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline 
• 66040-34-4 1-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone 
• 189277-01-8 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-oxide 
• 20412-85-5 2-benzyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 66040-35-5 2-chloroacetyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinoline 
• 853650-67-6 (+)-2-(hept-6-ynyl)-6,7-dimethoxy-1S-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 853650-66-5 (-)-2-(hept-6-ynyl)-6,7-dimethoxy-1R-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 853650-69-8 (+)-6,7-dimethoxy-2-(oct-7-ynyl)-1S-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 853650-68-7 (-)-6,7-dimethoxy-2-(oct-7-ynyl)-1R-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Enantioselective addition of organolithium reagents to 3,4-dihydroisoquinoline in the presence of (-)-sparteine as an external ligand. Application for the synthesis of isoquinoline alkaloids

Three isoquinoline alkaloids, (-)-salsolidine 2, (+)-carnegine 6 and (-)-1-phenyl-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 7, were obtained in high yield and with 17-46% e.e. by the enantioselective additions of organolithium reagents to dihydroisoquinolines 1 and 5, in the presence of (-)-sparteine as a chiral ligand.

Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues

A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.

Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.

Direct α-C-H bond functionalization of unprotected cyclic amines

Cyclic amines are ubiquitous core structures of bioactive natural products and pharmaceutical drugs. Although the site-selective abstraction of C-H bonds is an attractive strategy for preparing valuable functionalized amines from their readily available parent heterocycles, this approach has largely been limited to substrates that require protection of the amine nitrogen atom. In addition, most methods rely on transition metals and are incompatible with the presence of amine N-H bonds. Here we introduce a protecting-group-free approach for the α-functionalization of cyclic secondary amines. An operationally simple one-pot procedure generates products via a process that involves intermolecular hydride transfer to generate an imine intermediate that is subsequently captured by a nucleophile, such as an alkyl or aryl lithium compound. Reactions are regioselective and stereospecific and enable the rapid preparation of bioactive amines, as exemplified by the facile synthesis of anabasine and (-)-solenopsin A.

Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides

On the basis of X-ray crystallographic studies of the complex of hCA II with 4-(3,4-dihydro-1H-isoquinoline-2-carbonyl)benzenesulfonamide (3) (PDB code 4Z1J), a novel series of 4-(1-aryl-3,4-dihydro-1H-isoquinolin-2-carbonyl)benzenesulfonamides (23-33) wa

Conjugates of salicylaldoximes and peripheral site ligands: Novel efficient nonquaternary reactivators for nerve agent-inhibited acetylcholinesterase

A new family of nonquaternary reactivators for nerve agent-inhibited human acetylcholinesterase (hAChE) were designed, synthesized and tested in this paper. It was found that salicylaldoximes were able to quickly cleave the P–S bond of organophosphate and avoid the reinhibition phenomenon in the reactivation process, but they lacked reactivating ability due to poor affinity for AChE. Based on a dual site binding strategy, different peripheral site ligands of AChE were introduced to achieve extra affinity. The in vitro reactivation experiments demonstrated that some of the yielding conjugates exhibited similar or even superior ability to reactivate sarin-, VX- or tabun-inhibited hAChE in comparison with the mono- and bis-pyridinium aldoximes currently used. Moreover, due to greatly improved lipophilicity, these nonquaternary conjugates hold promise for the development of efficient centrally activating reactivators.

(η5-Pentamethylcyclopentadienyl)iridium Complex Catalyzed Imine Reductions Utilizing the Biomimetic 1,4-NAD(P)H Cofactor and N-Benzyl-1,4-dihydronicotinamide as the Hydride-Transfer Agent

The interaction between synthetic organometallic complexes and metabolic cofactors has proven to be a newly emerging topic in bioorganometallic chemistry. Thus, the first cationic Cp*Ir-catalyzed (Cp=η5-pentamethylcyclopentadienyl) imine reduction in neutral buffered aqueous medium was examined. The reaction was found to proceed through hydride transfer from NADH as the hydride source at room temperature in air. Cationic Cp*Ir complexes proved to be the most efficient catalysts for this transformation. We also highlighted that the choice of the proton source was essential. The method was subsequently applied to cyclic and noncyclic imines. Eventually, the concept was extended to the reductive alkylation of one amine.

In Vivo Evaluation of Selective Carbonic Anhydrase Inhibitors as Potential Anticonvulsant Agents

Epilepsy is a common neurological disorder caused by an imbalance between inhibitory and excitatory neurotransmission. It is well known that neuronal excitability is related to γ-aminobutyric acid (GABA)ergic depolarization. HCO3?-dependent depolarization can be suppressed by membrane-permeable inhibitors of carbonic anhydrase. We previously identified some isoquinoline sulfonamides as potent and selective inhibitors of the human carbonic anhydrase II and VII (hCA II and hCA VII) isoforms. Given that hCA II and hCA VII are specific isoforms involved in GABA-mediated neuronal excitation, we hypothesized that they could represent the biological target for the development of new anticonvulsant agents. Therefore, for selected isoquinoline sulfonamides, we preliminarily tested their ability to prevent audiogenic seizures in DBA/2 mice. All compounds were evaluated after intraperitoneal administration, and some of them proved to protect the mice against convulsions. Among this series of compounds, several derivatives showed combined in vivo efficacy with inhibitory effects toward the targeted carbonic anhydrases (i.e., hCA II and hCA VII). Specifically, the most interesting molecule was 1-(4-aminophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamide (6), which proved to be a more active and selective hCA VII inhibitor than the reference compound topiramate. Further studies to explore the in vivo pharmacokinetic profile of the most active compounds may help to provide insight into the future design of selective hCA VII inhibitors.

NOVEL CAPSAZEPINE ANALOGS FOR THE TREATMENT OF CANCER AND OTHER PROLIFERATIVE DISEASES

The present disclosure relates generally to derivatives of capsazepine and methods of use thereof In some aspects, the present disclosure relates to using capsazepine derivatives to treat cancer or other hyperproliferative diseases. In some aspects of the

O-Naphthoquinone-Catalyzed Aerobic Oxidation of Amines to (Ket)imines: A Modular Catalyst Approach

A modular aerobic oxidation of amines to imines has been achieved using an ortho-naphthoquinone (o-NQ) catalyst. The cooperative catalyst system of o-NQ and Cu(OAc)2 enabled the formation of homocoupled imines from benzylamines, while the presence of TFA helped the formation of cross-coupled imines in excellent yields. The current mild aerobic oxidation protocol could also be applied to the oxidation of secondary amines to imines or ketimines with the help of cocatalyst, Ag2CO3, with excellent yields.