Heterocyclic Building Blocks-Tetrahydroisoquinoline

Synthesis and biological evaluation of 3-alkyl-dihydrotetrabenazine derivatives as vesicular monoamine transporter-2 (VMAT2) ligands was written by Zheng, Pinguan;Lieberman, Brian P.;Choi, Seok Rye;Ploeessl, Karl;Kung, Hank F.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Reference of 2328-12-3 This article mentions the following:

In the search of new probes for in vivo brain imaging of vesicular monoamine transporter type 2 (VMAT2), an efficient synthesis of a novel series of 3-alkyldihydrotetrabenazine (DTBZ) derivatives was developed. The affinity of VMAT2 was evaluated by an in vitro inhibitory binding assay using [¹²⁵I]-iodovinyl-TBZ or [¹⁸F](+)-FP-DTBZ as radioligands in rat striatal tissue homogenates. New DTBZ derivatives exhibited moderate to good binding affinity to VMAT2. Among these new ligands, 9,10-dimethoxy-3-(2-methylallyl)-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol showed the best affinity for VMAT2 (K _i = 5.98 nM) and may be a useful lead compound for future structure-activity studies. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Reference of 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. Arene/Ru/TsDPEN complexes bearing a heterocyclic group catalyze the asymmetric transfer hydrogenation (ATH) of 1-aryl dihydroisoquinolines (DHIQs) to provide tetrahydroisoquinolines of high enantiomeric excess.Reference of 2328-12-3

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

De-novo design, synthesis and evaluation of novel 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as HIV-1 reverse transcriptase inhibitors was written by Chander, Subhash;Ashok, Penta;Singh, Anupam;Murugesan, Sankaranarayanan. And the article was included in Chemistry Central Journal in 2015.Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

Background: Acquired Immune Deficiency Syndrome (AIDS) is the advanced stage of infection caused by Human Immunodeficiency Virus (HIV). HIV/AIDS had a great impact on society, both as an illness and as a source of discrimination. Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs) are structurally diverse group of compounds which binds to Reverse Transcriptase (RT) enzyme of HIV. Like other anti-HIV drugs, long-term clin. effectiveness of approved NNRTIs has been hampered due to the rapid development of drug resistance. So, there is an urgent need to discover the NNRTIs, which can be effective against the drug sensitive as well as drug resistant strains of HIV-1 RT. Results: Two series of novel thirty, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline analogs (5a-o) and (8a-o) were designed and synthesized as inhibitor of HIV-1 reverse transcriptase. All the synthesized compounds were characterized by IR spectroscopy, proton NMR spectroscopy, mass spectroscopy and evaluated for in-vitro RT inhibitory activity. Among the tested compounds, eighteen compounds exhibited more than 50 % inhibition at tested 100 μM concentration, in which two compounds 8h and 8l showed promising inhibition (74.82 and 72.58 %) resp. The preliminary structure-activity relationship (SAR) of the test compounds and docking studies of the two significantly active compounds 8h and 8l were performed to examine their putative binding with HIV-RT. Predicted physiochem. parameters of the synthesized compounds were within the acceptable range of drugable properties. Conclusion: The results obtained from this investigation revealed that, the synthesized compounds (5a-o) and (8a-o) showed moderate to promising HIV-1 RT inhibition activity. The overall SAR studies can help in identification of further lead as well as in designing of newer potential inhibitor of HIV-1 RT. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. An efficient CuCl2-catalyzed coupling of nonfunctionalized tetrahydroisoquinolines with organozinc reagents under aerobic conditions proceeds in high yields under mild reaction conditions and is broadly applicable to a wide range of substrates. The reaction involves an iminium ion intermediate that is formed via a SET process.Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Topological pattern for the search of new active drugs against methicillin resistant Staphylococcus aureus was written by Bueso-Bordils, Jose I.;Perez-Gracia, Maria T.;Suay-Garcia, Beatriz;Duart, Maria J.;Martin Algarra, Rafael V.;Lahuerta Zamora, Luis;Anton-Fos, Gerardo M.;Aleman Lopez, Pedro A.. And the article was included in European Journal of Medicinal Chemistry in 2017.SDS of cas: 2328-12-3 This article mentions the following:

Mol. topol. was used to develop a math. model capable of classifying compounds according to antimicrobial activity against methicillin resistant Staphylococcus aureus (MRSA). Topol. indexes were used as structural descriptors and their relation to antimicrobial activity was determined by using linear discriminant anal. This topol. model establishes new structure activity relationships which show that the presence of cyclopropyl, chlorine and ramification pairs at a distance of two bonds favor this activity, while the presence of tertiary amines decreases it. This model was applied to a combinatorial library of a thousand and one 6-fluoroquinolones, from which 117 theor. active mols. were obtained. The compound 10 and five new quinolones were tested against MRSA. They all showed some activity against MRSA, although compounds 6, 8 and 9 showed anti-MRSA activity similar to ciprofloxacin. This model was also applied to 263 theor. antibacterial agents described by the authors in a previous work, from which 34 were predicted as theor. active. Anti-MRSA activity was found bibliog. in 9 of them (ensuring at least 26% of success), and from the rest, 3 compounds were randomly chosen and tested, finding mitomycin C to be more active than ciprofloxacin. The results demonstrate the utility of the mol. topol. approaches for identifying new drugs active against MRSA. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3SDS of cas: 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This is no longer generally accepted by the scientific community.SDS of cas: 2328-12-3

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Discovery of aromatic amides with triazole-core as potent reversal agents against P-glycoprotein-mediated multidrug resistance was written by Qiu, Qianqian;Zhu, Jilan;Chen, Qiutong;Jiang, Ziqian;Xu, Jiting;Jiang, Xueting;Huang, Wenlong;Liu, Zhongquan;Ye, Jing;Xu, Xiaojuan. And the article was included in Bioorganic Chemistry in 2019.Quality Control of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a major impediment for clin. cancer therapy. 19 novel aromatic amides with triazole-core as MDR reversal agents were designed and synthesized via click chem. to reverse MDR. Among them, compound 42 was identified as the most promising candidate with high potency (EC₅₀ = 78.1 ± 5.4 nM), low cytotoxity (SI > 1282) and persistent duration in reversing doxorubicin (DOX) resistance in K562/A02 cells. 42 also enhanced the potency of other P-gp associated cytotoxic agents with different structures. In further study, remarkably increased intracellular accumulation of Rh123 and DOX in K562/A02 cells was achieved by compound 42, while CYP3A4 activity had no change by compound 42. These results indicate that compound 42 as a relatively safe modulator of P-gp-mediated MDR has good potential for further development. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Quality Control of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.Quality Control of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Evaluation of (4-Arylpiperidin-1-yl)cyclopentanecarboxamides as high-affinity and long-residence-time antagonists for the CCR2 receptor was written by Vilums, Maris;Zweemer, Annelien J. M.;Dilanchian, Arian;van Veldhoven, Jacobus P. D.;de Vries, Henk;Brussee, Johannes;Saunders, John;Stamos, Dean;Heitman, Laura H.;IJzerman, Adriaan P.. And the article was included in ChemMedChem in 2015.Computed Properties of C10H11ClF3N This article mentions the following:

Animal models suggest that the chemokine ligand 2/CC-chemokine receptor 2 (CCL2/CCR2) axis plays an important role in the development of inflammatory diseases. However, CCR2 antagonists have failed in clin. trials because of a lack of efficacy. We previously described a new approach for the design of CCR2 antagonists by the use of structure-kinetics relationships (SKRs). Herein we report new findings on the structure-affinity relationships (SARs) and SKRs of the reference compound MK-0483, its diastereomers, and its structural analogs as CCR2 antagonists. The SARs of the 4-arylpiperidine group suggest that lipophilic hydrogen-bond-accepting substituents at the 3-position are favorable. However, the SKRs suggest that a lipophilic group with a certain size is desired [e.g., 3-Br: K_i=2.8 nΜ, residence time (t_res)=243 min; 3-iPr: K_i=3.6 nΜ, t_res=266 min]. Alternatively, addnl. substituents and further optimization of the mol., while keeping a carboxylic acid at the 3-position, can also prolong t_res; this was most prominently observed in MK-0483 (K_i=1.2 nΜ, t_res=724 min) and a close analog (K_i=7.8 nΜ) with a short residence time. In the experiment, the researchers used many compounds, for example, 7-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 220247-87-0Computed Properties of C10H11ClF3N).

7-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 220247-87-0) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. Among them, 1-substituted tetrahydroisoquinolines are privileged scaffolds in drugs and pharmaceuticals. Arene/Ru/TsDPEN complexes bearing a heterocyclic group catalyze the asymmetric transfer hydrogenation (ATH) of 1-aryl dihydroisoquinolines (DHIQs) to provide tetrahydroisoquinolines of high enantiomeric excess.Computed Properties of C10H11ClF3N

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters was written by Orjales, Aurelio;Mosquera, Ramon;Toledo, Antonio;Pumar, M. Carmen;Garcia, Neftali;Cortizo, Lourdes;Labeaga, Luis;Innerarity, Ana. And the article was included in Journal of Medicinal Chemistry in 2003.Recommanded Product: 2328-12-3 This article mentions the following:

In a wide search program toward new, efficient, and fast-acting antidepressant drugs, series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane) were prepared These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT_1A and 5-HT_2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidines I (R¹ = H, Me, MeCO; R² = H, 3-F, 4-F, 4-Cl, 4-Me; R³ = H, 2-CN, 4-O₂N, 4-MeO, 2-Ph, etc.) showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT_1A and 5-HT_2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α₂ receptor. Several of these enantiomers, (-)-I (R¹ = R² = H; R³ = 2-F), (-)-I (R¹ = R² = H; R³ = 3-F), (-)-I (R¹ = H; R² = 3-F; R³ = 2-F), (+)-I (R¹ = H; R² = R³ = 3-F), displayed a dual binding profile with affinities for SERT and NET with K_i < 25 nM and a NET/SERT ratio <10. (-)-I (R¹ = R² = H; R³ = 3-F) (coded as F-98214-TA for development studies) showed a dual binding profile with very high affinity values for SERT and NET (K_i = 1.9 and 13.5 nM, resp.), and further pharmacol. characterization is in progress for its evaluation as a antidepressant. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Recommanded Product: 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. An efficient CuCl2-catalyzed coupling of nonfunctionalized tetrahydroisoquinolines with organozinc reagents under aerobic conditions proceeds in high yields under mild reaction conditions and is broadly applicable to a wide range of substrates. The reaction involves an iminium ion intermediate that is formed via a SET process.Recommanded Product: 2328-12-3

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Ring-opening reactions of halogenated N-aryl-1,2,3,4-tetrahydroisoquinoline and 2,3,4,5-tetrahydro-1H-2-benzazepine derivatives was written by Stanley, Alan L.;Stanforth, Stephen P.. And the article was included in Journal of Heterocyclic Chemistry in 1995.Recommanded Product: 2328-12-3 This article mentions the following:

Title compounds I [n = 1, 2; R = H, OMe; R¹ = C₆F₅, tetrafluoropyrid-4-yl, C₆Cl₅] were prepared and their ring-opening reactions with N-bromosuccinimide investigated. I [n = 1, R = H, OMe, R¹ = C₆F₅] gave a mixture of products which did not contain any significant quantity of the aldehydes II whereas the other I gave II exclusively. Compound 10 similarly gave the aldehyde 11 when treated with NBS. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Recommanded Product: 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is present in a number of drugs, such as tubocurarine, one of the quaternary ammonium muscle relaxants. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.Recommanded Product: 2328-12-3

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Synthesis and in vitro evaluation of tetrahydroisoquinolinyl benzamides as ligands for σ receptors was written by Xu, Rong;Lever, John R.;Lever, Susan Z.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Category: tetrahydroisoquinoline This article mentions the following:

5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2,3-dimethoxy-benzamide (I) is one of the most potent and selective σ ₂ receptor ligands reported to date. Previous structure-activity relationship studies of such tetrahydroisoquinolinyl benzamides have focused on the linker that connects the ring systems and the effects of benzamide ring substituents. The present study explores the effects of fusing methylene-, ethylene-, and propylenedioxy rings onto the tetrahydroisoquinoline in place of the two methoxy groups. These modifications decreased σ₂ affinity by 8- to 12-fold, with no major differences noted with ring size. By contrast, the methylenedioxy analog showed a 10-fold greater σ₁ affinity than I, and progressively lower σ₁ affinities were then noted with increasing ring size. The tetrahydroisoquinoline ring of I was opened to study the effects of greater conformational fluidity on σ receptor binding. The σ₂ affinity of the open-ring compound decreased by 1700-fold, while σ₁ affinity was not changed. Thus, a constrained tetrahydroisoquinoline ring system is key to the exceptional σ₂ receptor binding affinity and selectivity of this active series. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Category: tetrahydroisoquinoline).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. Because of the high biological relevance of compounds possessing the 1,2,3,4-tetrahydroisoquinoline framework, a large number of synthetic approaches towards the creation of an isoquinoline or 1,2,3,4-tetrahydroisoquinoline core are presently known. However, synthetic routes to tetrahydroisoquinoline derivatives containing fluorine atom(s) in their structure are not particularly abundant.Category: tetrahydroisoquinoline

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Design, synthesis and evaluation of novel triazole core based P-glycoprotein-mediated multidrug resistance reversal agents was written by Jiao, Lei;Qiu, Qianqian;Liu, Baomin;Zhao, Tianxiao;Huang, Wenlong;Qian, Hai. And the article was included in Bioorganic & Medicinal Chemistry in 2014.Recommanded Product: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

A novel series of triazol-N-ethyl-tetrahydroisoquinoline based compounds were designed and synthesized via click chem. Most of the synthesized compounds showed P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) reversal activities. Among them, compound 7 with little cytotoxicity towards GES-1 cells (IC₅₀ >80 μM) and K562/A02 cells (IC₅₀ >80 μM) exhibited more potency than verapamil (VRP) on increasing anticancer drug accumulation in K562/A02 cells. Moreover, compound 7 could significantly reverse MDR in a dose-dependent manner and also persist longer chemo-sensitizing effect than VRP with reversibility. Further mechanism studies revealed that compound 7 in reversing MDR revealed that it could remarkably increase the intracellular accumulation of both rhodamine-123 (Rh123) and adriamycin (ADM) in K562/A02 cells as well as inhibit their efflux from the cells. These results suggested that compound 7 showed more potency than the classical P-gp inhibitor VRP under the same conditions, which may be a promising P-gp-mediated MDR modulator for further development. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Recommanded Product: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. An oxidative C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents is mediated by diethyl azodicarboxylate (DEAD). This C-H activation under metal-free conditions delivers target compounds, including some naturally occurring alkaloids, in good yields.Recommanded Product: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Design, synthesis and biological evaluation of a series of novel GPR40 agonists containing nitrogen heterocyclic rings was written by Sun, Zhaozhu;Zhou, Tian;Pan, Xuan;Yang, Ying;Huan, Yi;Xiao, Zhiyan;Shen, Zhufang;Liu, Zhanzhu. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2018.COA of Formula: C14H18BrNO2 This article mentions the following:

A novel series of GPR40 agonists is designed by introducing nitrogen-containing heterocyclic ring at the terminal Ph ring of TAK-875 (I) with the aim of decreasing its lipophilicity. Three different β-substituted phenylpropionic acids were investigated as the acidic components. A total of 34 compounds have been synthesized, among which, compound II exhibited comparable GPR40 agonistic activity in vitro with TAK-875 and relatively lower lipophilicity through calculation (II: EC₅₀ = 1.2 μM, cLogP = 1.3; TAK-875: EC₅₀ = 5.1 μM, cLogP = 3.4). Moreover, compound II was able to enhance the insulin secretion of primary islets isolated from normal ICR mice and showed no obvious inhibition against cytochromes P 450 in vitro. In vivo, compound II exhibited efficacy in oral glucose tolerance test (oGTT) in normal ICR mice. In the experiment, the researchers used many compounds, for example, tert-Butyl 5-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (cas: 215184-78-4COA of Formula: C14H18BrNO2).

tert-Butyl 5-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (cas: 215184-78-4) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.COA of Formula: C14H18BrNO2

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem