19716-56-4

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzyl-1,2,3,4-tetrahydroisoquinoline is used as a potential therapeutic agent for the treatment of neurological disorders such as Parkinson's disease and depression. Its agonistic effect on dopamine D1 receptors and its inhibitory action on monoamine oxidase contribute to its potential in managing these conditions by modulating neurotransmitter levels and improving neuronal function.
Used in Oncology Research:
In the field of oncology, 1-benzyl-1,2,3,4-tetrahydroisoquinoline is being studied for its ability to inhibit the growth of cancer cells. Its potential as an anticancer agent is attributed to its capacity to interfere with cellular processes that promote tumor growth and proliferation, offering a novel approach to cancer treatment.
Used in Neuroprotective Research:
1-Benzyl-1,2,3,4-tetrahydroisoquinoline is also being investigated for its neuroprotective effects. Its potential to shield neurons from damage or degeneration makes it a candidate for research into neurodegenerative diseases and conditions where neuronal protection is crucial for therapeutic intervention.
While the provided materials do not specify different applications in various industries, the above uses are inferred from the compound's pharmacological properties and areas of research interest. Further studies may reveal additional applications in other fields such as drug delivery systems or as a component in the development of new pharmaceutical formulations.

InChI:InChI=1/C16H17N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-9,16-17H,10-12H2

Upstream product

• 24853-83-6 1-benzyl-3,4-dihydro-isoquinoline 
• 3230-65-7 3,4-dihydroisoquinoline 
• 766-04-1 benzyllithium 
• 6907-59-1 1-benzylisoquinoline 
• 81763-78-2 [1-(1-Benzyl-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-cyclohexyl-amine 
• 78702-61-1 2-bis(dimethylamino)phosphinoyl-1-benzyl-1,2,3,4-tetrahydroisoquinoline 
• 161521-64-8 (E)-2-(2-styrylphenyl)ethanamine 
• 13605-95-3 N-benzyl-1,2,3,4-tetrahydroisoquinoline 
• 6921-34-2 benzylmagnesium chloride 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 314265-06-0 1-benzyl-2-pivaloyl-1,2,3,4-tetrahydroisoquinoline 
• 64-04-0 phenethylamine 

Downstream Products

• 10225-29-3 1-benzyl-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 96550-45-7 1-Benzyl-3,4-dihydro-1H-isoquinoline-2-carbonyl chloride 
• 1394957-84-6 (1S)-1-benzyl-2-(3-mesitylpropanoyl)-1,2,3,4-tetrahydroisoquinoline 
• 57680-86-1 (1S)-1-benzyl-1,2,3,4-tetrahydroisoquinoline 
• 57680-87-2 (1R)-1-benzyl-1,2,3,4-tetrahydroisoquinoline 
• 138967-33-6 1-phenylmethy-3,4-dihydro-1H-isoquinoline-2-carboxaldehyde 
• 131-10-2 (-)-berbine 
• 4831-01-0 1-benzyl-2,3-dihydro-1H-indene 
• 138949-61-8 5,6-dihydrodibenzoquinolizinium chloride 

Related news

Short communicationDeprenyl decreases an endogenous parkinsonism-inducing compound, 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINE (cas 19716-56-4) in mice: in vivo and in vitro studies09/08/2019

We examined the effect of deprenyl, a promising drug for the therapy of Parkinson's disease on the formation of a parkinsonism-inducing compound, 1-benzyl-1,2,3,4-tetrahydroisoquinoline (1BnTIQ). The 1BnTIQ content was significantly decreased in the brain of deprenyl-treated mouse in vivo, ...detailed

NeuropharmacologyResearch PaperSingle administration of 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINE (cas 19716-56-4) increases the extracellular concentration of dopamine in rat striatum09/05/2019

We performed a combined neurochemical and behavioral study to determine the effects of 1-benzyl-1,2,3,4-tetrahydroisoquinoline (1-BnTIQ) on the extracellular dopamine concentrations in the striatum. Single dose administration of 1-BnTIQ (20, 40, and 80 mg/kg i.p.) increased striatal dopamine ext...detailed

1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINE (cas 19716-56-4) (1BnTIQ), An Endogenous Neurotoxin, Induces Dopaminergic Cell Death Through Apoptosis09/04/2019

Endogenous MPTP-like neurotoxins such as 1-benzyl-1,2,3,4-tetrahydroisoquinoline (1BnTIQ) have been suspected in the etiology of Parkinson’s disease (PD). 1BnTIQ was found in a concentration three times higher in cerebrospinal fluid of PD brains than control subjects [J. Neurochem. 65 (6) (1995...detailed

1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINE (cas 19716-56-4) passes through the blood–brain barrier of rat brain: An in vivo microdialysis study08/31/2019

Previous work has established that 1-benzyl-1,2,3,4-tetrahydroisoquinoline (1-BnTIQ) causes a parkinsonian syndrome in rats. The present study reports the blood–brain barrier (BBB) permeability of 1-BnTIQ in freely moving rats with the aid of in vivo microdialysis-based measurements. The microd...detailed

Relevant academic research and scientific papers

Anionic Rearrangement of BF3-complexed N-Allyl and Aryl Tetrahydroisoquinolines.

BF3-complexed N-Allyl and N-benzyl tetrahydroisoquinolines react, at -20 deg C to 0 deg C in THF, with sec-BuLi to give 1-substituted tetrahydroisoquinolines.

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.

Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts

A ruthenium-catalyzed photoredox coupling of substituted N-aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. Furthermore, secondary alkyl and allyl groups were also successfully introduced via the same method. Additionally, the typically applied N-phenyl group in the THIQ substrate could be replaced by the cleavable p-methoxyphenyl (PMP) group and successful N-deprotection was demonstrated.

Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells

Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a,7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine- and benzylisoquinoline-type alkaloids. In addition, 3-30 μM nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 μM N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 μM nuciferine inhibited the expression of TRP-2 mRNA.

4,5-Dihydrothiazoline - A new protecting and activating group for generation of α-aminocarbanions of secondary amines

4,5-Dihydrothiazoline has been successfully used as a protecting and activating group for synthesis of various 1-substituted 1,2,3,4- tetrahydroisoquinolines via a lithiation-electrophillic substitution reaction sequence. Copyright Taylor & Francis Group, LLC.

Steps towards a practical synthesis of macrocyclic bisbenzylisoquinolines

There are more than 400-reported bisbenzylisoquinoline alkaloids, many with interesting biological activity, but the reported syntheses are long and low yielding. As a result, there have been no systematic attempts at exploitation of the potential therapeutic applications. The concept of a sulfur 'stitch', restricting the conformational freedom of intermediates in the synthesis, will potentially allow analogues of the natural products to be prepared using relatively efficient routes. The synthesis of intermediate sulfur heterocycles is reported, based on 2,8-dimethylphenoxathiin, leading via 2,8-bis(bromomethyl) phenoxathiin-10,10-dioxide to a synthesis of 3,4,8,9-tetrahydro-13-oxa-6-thia-2, 10-diazapentacene, a key potential intermediate on the route to a variety of macrocyclic bisbenzylisoquinolines.

The Cp2TiMe2-catalyzed intramolecular hydroamination/cyclization of aminoalkynes

Cp2TiMe2 has been found to be a competent catalyst for the intramolecular hydroamination/cyclization of aminoalkynes. In the presence of 5.0 mol% Cp2TiMe2, the hydroamination reactions proceed smoothly at 100-110°C to give five- and six-membered cyclic imines within 4-6 h. After subsequent reduction performed with zinc-modified NaBH3CN at room temperature cyclic amines can be isolated in good yields.

Inhibition of dopamine receptors by endogenous amines: Binding to striatal receptors and pharmacological effects on locomotor activity

Endogenous amine 1-benzyl-1,2,3,4-tetrahydroisoquinoline (1BnTIQ) derivatives are synthesized, and their activity for dopaminergic systems are evaluated in vitro and in vivo by receptor binding assay and pharmacological tests. It is proposed that 1BnTIQ d

A highly efficient synthesis of 1-methyl-, 1-benzyl-, and 1-phenyl-1,2,3,4-tetrahydroisoquinolines by a modified pummerer reaction

(±)-1-Methyl- (13b), (±)-1-benzyl- (13c), and (±)-1-phenyl- (13d)-1,2,3,4-tetrahydroisoquinolines, which are supposed to participate in the pathogenesis of Parkinson's disease, were prepared by using a modified Pummerer reaction as a key step in excellent overall yields from the commercially available ketones (4b-c).

Photophysics and photochemistry of intramolecular stilbene-amine exciplexes

The photophysical and photochemical behavior of a series of trans- (aminoalkyl)stilbenes in which a primary, secondary, or tertiary amine is appended to the stilbene ortho position with a methyl, ethyl, or propyl linker has been investigated. The tertiary