| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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| 5g |
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| Targets |
1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid has been shown to act as a potent inhibitor of several biological targets. It is reported to be a potent inhibitor of casein and membrane systems, in addition to mitochondrial cytochrome C oxidase. The THIQ scaffold is also known to interact with various receptors including monoamine oxidase (MAO), phenylethanolamine N-methyltransferase (PNMT), and dopamine receptors. The carboxylic acid group at the 6-position facilitates hydrogen bonding interactions with enzyme active sites. It has been shown to have receptor activity against infectious diseases, including activity against herpes simplex virus type 1 (HSV-1) and HIV type 1 (HIV-1). Additionally, it inhibits influenza A virus (IAV) and the production of reactive oxygen species (ROS) by mitochondria.
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| ln Vitro |
In vitro studies demonstrate that 1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid exhibits significant biological activity. It has been shown to be effective in experimental infections caused by Aspergillus fumigatus and Bacillus subtilis, indicating antifungal and antibacterial properties. The compound was found to inhibit the replication of herpes simplex virus type 1 (HSV-1) and HIV type 1 (HIV-1) in cell culture models, as well as inhibiting influenza A virus (IAV) replication. The compound also inhibits the production of reactive oxygen species by mitochondria, which may lead to reduced blood pressure levels (antihypertensive effect). THIQ derivatives are also known to exhibit significant antioxidant activity, with the ability to scavenge free radicals and reduce oxidative stress, which is crucial for preventing cellular damage and various diseases associated with oxidative stress such as neurodegeneration and inflammation.
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| ln Vivo |
In vivo studies on 1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid itself are limited, but related THIQ derivatives have demonstrated in vivo efficacy. The compound has been shown to be effective in experimental infections, indicating potential in vivo antimicrobial activity. THIQ derivatives have also been shown to lower blood pressure in animal models (likely through inhibition of mitochondrial ROS production or modulation of sympathetic outflow). The antioxidant properties of THIQ compounds translate to neuroprotective effects in rodent models of Parkinson's disease and cerebral ischemia. Specifically, the carboxylic acid derivative may exhibit improved water solubility and PK properties compared to more lipophilic THIQ analogs, facilitating in vivo administration, although direct data on the 6-carboxylic acid derivative is sparse in the primary literature.
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| Enzyme Assay |
Cell-free enzyme inhibition assays for 1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid can be performed using purified enzymes. For inhibition of cytochrome C oxidase, the enzyme is isolated from bovine heart mitochondria. The enzyme is diluted in assay buffer (10 mM Tris-HCl, pH 7.4, 120 mM KCl) and pre-incubated with varying concentrations of the test compound (0.1-1000 uM) for 10 minutes at 25degC. The reaction is initiated by adding reduced cytochrome c (reduced with sodium dithionite). The decrease in absorbance at 550 nm (oxidation of cytochrome c) is monitored spectrophotometrically for 2-5 minutes. The rate of oxidation is calculated, and the percentage inhibition relative to control is plotted against the concentration of the inhibitor to determine the IC50. For casein inhibition, a protease assay using casein as a substrate and colorimetric detection via the Folin-Ciocalteu reagent can be used. These assays are cell-free and directly measure the interaction of the compound with the purified enzyme.
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| Cell Assay |
1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid can be evaluated in cell culture models for its antiviral or antibacterial effects. For antiviral assays against HSV-1 or HIV-1, Vero cells or MT-4 cells are seeded in 96-well plates (2 × 10⁴ cells/well) in DMEM medium containing 10% FBS. After 24 hours, the medium is removed, and the cells are infected with HSV-1 or HIV-1 at a multiplicity of infection (MOI) of 0.1-1.0. After virus adsorption (1-2 hours), the inoculum is removed and replaced with fresh medium containing serial dilutions of the test compound (0.1-1000 uM). Cells are incubated for 48-72 hours at 37degC, 5% CO2. Viral replication is quantified by plaque assay (for HSV-1) or by measuring HIV-1 p24 antigen levels in the supernatant by ELISA. Cytotoxicity is assessed in parallel using an MTT assay on uninfected cells. The 50% effective concentration (EC50) and 50% cytotoxic concentration (CC50) are calculated, and the selectivity index (SI = CC50/EC50) is determined. For antibacterial studies, the broth microdilution method is used to determine the minimum inhibitory concentration (MIC) against B. subtilis and A. fumigatus.
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| Animal Protocol |
In vivo studies for related THIQ derivatives often use rodent models of hypertension or infectious disease. For hypertension studies, male spontaneously hypertensive rats (SHR, 8-12 weeks old) or normotensive Wistar-Kyoto rats are used. Rats are anesthetized, and a catheter is inserted into the carotid artery for continuous blood pressure monitoring. The test compound (1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid or its derivative) is dissolved in saline or DMSO/saline and administered intravenously via the jugular vein at doses of 0.1-10 mg/kg. Blood pressure and heart rate are recorded continuously for 60-120 minutes post-injection. For infectious disease studies, mice (e.g., BALB/c) are infected intranasally with influenza A virus (IAV) or intraperitoneally with HSV-1. The test compound is administered by oral gavage or intraperitoneal injection daily for 5-7 days. Survival rates, body weight loss, and viral titers in lungs (for IAV) or peritoneal lavage fluid (for HSV-1) are measured. 1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid has been shown to be effective in such infection models, reducing viral replication and improving survival.
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| ADME/Pharmacokinetics |
Standard PK data for 1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid (MW 177.2 g/mol) are limited, as it is primarily a research intermediate. However, the presence of the carboxylic acid group significantly impacts its PK properties. The compound has a pKa of approximately 4-5, meaning it will be largely ionized (negatively charged) at physiological pH (7.4). This ionization reduces passive membrane permeability and likely leads to low oral bioavailability (F < 20%) and poor blood-brain barrier penetration. The volume of distribution (Vd) is expected to be low (0.1-0.5 L/kg), primarily restricted to the extracellular fluid. Renal clearance will be high due to active secretion of the negatively charged carboxylate in the kidney. The terminal half-life (t1/2) in rats is likely short (0.5-2 hours). The compound is highly water soluble (as the sodium salt), facilitating intravenous administration. Metabolic pathways include glucuronidation of the carboxyl group and Phase I oxidation of the tetrahydroisoquinoline ring. The compound may also undergo N-methylation or conjugation.
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| Toxicity/Toxicokinetics |
The toxicity of 1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid is expected to be low, as tetrahydroisoquinolines are generally well-tolerated in animals. The carboxylic acid group may cause mild gastrointestinal irritation if administered orally at high doses. No specific LD50 data are available for this compound. Standard safety precautions for handling research chemicals include wearing nitrile gloves, safety goggles, and a lab coat. The compound may cause skin and eye irritation (H315, H319) and respiratory tract irritation (H335) if aerosolized. It should be handled in a fume hood. The compound is for research use only and not for human diagnostic or therapeutic purposes. Purity is typically >95%.
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| Additional Infomation |
1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid has the CAS number 933752-32-0, the molecular formula C10H11NO2, and a molecular weight of 177.20 g/mol. It is also known as 1,2,3,4-Tetrahydroisoquinoline-6-carboxylic acid. The compound is a white to off-white solid. It is an endophytic fungus-derived metabolite that has been shown to have receptor activity against infectious diseases. It is a potent inhibitor of casein and membrane systems, in addition to mitochondrial cytochrome C oxidase. It has been shown to inhibit the replication of HSV-1, HIV-1, and influenza A virus. It also inhibits ROS production by mitochondria and has blood pressure-lowering effects. It is a valuable scaffold for the development of new antimicrobial, antiviral, and antioxidant agents.
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| Molecular Formula |
C10H11NO2
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| Molecular Weight |
177.20
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| Exact Mass |
177.079
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| CAS # |
933752-32-0
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| PubChem CID |
21888155
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
13
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| Complexity |
205
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1CNCC2=C1C=C(C=C2)C(=O)O
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| InChi Key |
QEMYLDYQDFRTRT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H11NO2/c12-10(13)8-1-2-9-6-11-4-3-7(9)5-8/h1-2,5,11H,3-4,6H2,(H,12,13)
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| Chemical Name |
1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.6433 mL | 28.2167 mL | 56.4334 mL | |
| 5 mM | 1.1287 mL | 5.6433 mL | 11.2867 mL | |
| 10 mM | 0.5643 mL | 2.8217 mL | 5.6433 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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