| Size | Price | Stock | Qty |
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| 50mg |
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| 500mg |
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| Targets |
1,2,3,4-Tetrahydro-beta-carboline-1-carboxylic acid is a heterocyclic compound that serves as a scaffold for the development of various pharmacologically active molecules. Structurally, it resembles the neurotransmitter serotonin and can interact with receptors of the central nervous system (CNS). Derivatives of this beta-carboline core have been studied for their affinity for benzodiazepine receptors, monoamine oxidase (MAO) enzymes, and other CNS targets. It is also a precursor to harmalan, tetrahydroharman, and harman in rats.
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| ln Vitro |
In vitro, 1,2,3,4-Tetrahydro-beta-carboline-1-carboxylic acid and its derivatives have been studied for their neuroactive properties. It can be converted to harmalan, tetrahydroharman, and harman in rats, which are known to affect the CNS. The compound itself can be used as a starting material in organic synthesis to produce more complex beta-carboline derivatives with potential biological activity. The compound is primarily used in chemical biology research.
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| ln Vivo |
In vivo, 1,2,3,4-Tetrahydro-beta-carboline-1-carboxylic acid has been detected as an endogenous component in the brain and other tissues in some animal species. It is also a metabolite of tryptophan in the presence of ethanol. beta-Carboline derivatives have been shown to exert effects on the CNS, including sedation, anxiety modulation, and tremor induction. The compound is metabolized in rats to harmalan, tetrahydroharman, and harman, which are known to have biological activities. It is used in research on neurodegenerative diseases.
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| Enzyme Assay |
There is no standard cell-free binding assay for this specific compound. However, a generic biochemical assay for beta-carbolines is the monoamine oxidase (MAO) inhibition assay. Recombinant human MAO-A or MAO-B is incubated with a fluorogenic substrate (e.g., kynuramine) and varying concentrations of the test compound. The product (4-hydroxyquinoline) is measured fluorometrically (excitation 315 nm, emission 380 nm). The half-maximal inhibitory concentration (IC50) is calculated from the inhibition curve. This compound is used as a reference standard.
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| Cell Assay |
An in vitro cellular assay for beta-carboline derivatives is a neuronal cell viability assay using SH-SY5Y human neuroblastoma cells. Cells are seeded in 96-well plates and treated with varying concentrations of the test compound (e.g., 0-500 microM) for 24-48 hours. Cell viability is measured using an MTT or CCK-8 assay. Additionally, the generation of reactive oxygen species (ROS) can be measured using a fluorescent dye such as DCFH-DA. These assays help assess the potential neurotoxic or neuroprotective effects.
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| Animal Protocol |
In vivo studies with beta-carboline derivatives are often conducted in rodents to study their effects on the CNS. For example, rats are administered the test compound (e.g., 5-50 mg/kg) via intraperitoneal (IP) injection or oral gavage. Behavioral tests such as the open field test (locomotor activity), elevated plus maze (anxiety), and rotarod (motor coordination) are performed. Additionally, brain tissue can be collected for analysis of monoamine levels (serotonin, dopamine, norepinephrine) using HPLC-ECD. The conversion of the compound to harmalan, tetrahydroharman, and harman can be measured by LC-MS/MS.
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| ADME/Pharmacokinetics |
1,2,3,4-Tetrahydro-beta-carboline-1-carboxylic acid has a molecular weight of 216.24 and a molecular formula of C12H12N2O2. It is a small, lipophilic molecule with a calculated LogP around 1-2. It is likely to have good cell permeability and moderate oral bioavailability. For in vivo studies, it can be formulated in vehicles such as 0.5% CMC-Na (carboxymethylcellulose sodium) or a mixture of DMSO, PEG300, Tween 80, and saline. Its metabolic half-life in rats is expected to be short (1-4 hours) due to rapid metabolism and conjugation. The compound is stable as a powder at -20degC.
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| Toxicity/Toxicokinetics |
Specific toxicity data for 1,2,3,4-Tetrahydro-beta-carboline-1-carboxylic acid is not available. beta-Carbolines, in general, can exhibit neurotoxic effects at high doses. Some beta-carbolines, such as harmane and norharmane, are found in tobacco smoke and have been associated with tremor, anxiety, and other neurological effects. However, this tetrahydro derivative is generally considered less toxic. It should be handled with standard laboratory safety precautions, including the use of gloves, goggles, and a lab coat. Inhalation and ingestion should be avoided.
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| References |
[1]. J Gynther,et al. Decarboxylation of 1,2,3,4-tetrahydro-beta-carboline-1-carboxylic acids in brain homogenate and catalysis by pyridoxal-5'-phosphate. Biochem Pharmacol.1986 Aug 15;35(16):2671-5.
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| Additional Infomation |
1,2,3,4-Tetrahydro-beta-carboline-1-carboxylic acid (CAS 6649-91-8) is a naturally occurring beta-carboline alkaloid that serves as a chemical building block for the synthesis of pharmacologically active compounds. It is related to the class of beta-carbolines, which include compounds with neuroactive, antineoplastic, and antimicrobial properties. This compound is used in the study of neurodegenerative diseases and as an analytical standard. It is not a drug and has no approved therapeutic indications. The compound is for research and development use only.
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| Molecular Formula |
C12H12N2O2
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| Molecular Weight |
216.24
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| Exact Mass |
216.09
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| CAS # |
6649-91-8
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| PubChem CID |
145879
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| Appearance |
Light brown to brown solid powder
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| Density |
1.377g/cm3
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| Boiling Point |
498.3ºC at 760 mmHg
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| Melting Point |
210-212ºC
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| Flash Point |
255.1ºC
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| Index of Refraction |
1.692
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| LogP |
1.768
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
16
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| Complexity |
295
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C2C(=C1)C3=C(C(C(=O)O)NCC3)N2
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| InChi Key |
XGCIVVYTCDKDLC-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H12N2O2/c15-12(16)11-10-8(5-6-13-11)7-3-1-2-4-9(7)14-10/h1-4,11,13-14H,5-6H2,(H,15,16)
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| Chemical Name |
2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-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 |
| 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) |
DMSO: 5 mg/mL (23.12 mM)
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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 | 4.6245 mL | 23.1225 mL | 46.2449 mL | |
| 5 mM | 0.9249 mL | 4.6245 mL | 9.2490 mL | |
| 10 mM | 0.4624 mL | 2.3122 mL | 4.6245 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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