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| Targets |
4-Chloro-L-phenylalanine targets tryptophan hydroxylase (TPH), the rate-limiting enzyme in serotonin biosynthesis. It acts as a potent inhibitor of both TPH isoforms, TPH1 and TPH2. By inhibiting TPH, the compound reduces the conversion of tryptophan to 5-hydroxytryptophan, thereby decreasing serotonin synthesis. This mechanism makes it a valuable tool for studying the role of serotonin in various physiological and pathological processes.
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| ln Vitro |
In vitro, 4-Chloro-L-phenylalanine acts as a potent inhibitor of tryptophan hydroxylase. Its activity is typically assessed by measuring its ability to inhibit TPH enzyme activity in tissue homogenates or cell lysates. The compound inhibits both TPH1 and TPH2 isoforms. Standard in vitro assays include enzyme activity assays measuring the conversion of tryptophan to 5-hydroxytryptophan, as well as measurement of serotonin levels in cell cultures or tissue samples using HPLC or ELISA-based detection.
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| ln Vivo |
In vivo, 4-Chloro-L-phenylalanine has been used to block serotonin synthesis by inhibiting tryptophan hydroxylase. It has been used to study its behavioral and electrographic effects on epileptic Senegalese baboons (Papio papio). By reducing serotonin levels, the compound can be used to investigate the role of serotonin in various physiological and behavioral processes, including mood regulation, sleep, appetite, and seizure susceptibility. The compound is primarily used as a research tool.
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| Enzyme Assay |
For non-cell-based enzyme assays, 4-Chloro-L-phenylalanine can be evaluated using purified tryptophan hydroxylase enzyme or tissue homogenates containing TPH. Enzyme activity assays are performed by incubating the enzyme with tryptophan and a cofactor such as tetrahydrobiopterin (BH4) in the presence of increasing concentrations of the test compound. The production of 5-hydroxytryptophan is measured using HPLC with fluorescence or electrochemical detection. IC50 values are calculated from the inhibition curves.
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| Cell Assay |
For in vitro cellular assays, cells expressing tryptophan hydroxylase (e.g., serotonergic neurons or cell lines) are cultured in appropriate media. Cells are treated with various concentrations of 4-Chloro-L-phenylalanine, and serotonin and 5-hydroxytryptophan levels in the cell culture supernatant or cell lysates are measured using HPLC or ELISA-based detection. The reduction in serotonin levels compared to control indicates TPH inhibition. Cytotoxicity is assessed using MTT or LDH assays to ensure that observed effects are not due to cell death.
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| Animal Protocol |
For in vivo animal studies, 4-Chloro-L-phenylalanine can be administered to rodents via intraperitoneal injection. In models of serotonin depletion, brain serotonin levels are measured following compound administration. In models of epilepsy, seizure threshold and severity are assessed. In behavioral studies, the compound's effects on mood, anxiety, and locomotor activity are evaluated. Dosing regimens vary depending on the specific model and desired exposure levels. Blood and tissue samples may be collected for pharmacokinetic analysis.
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| ADME/Pharmacokinetics |
4-Chloro-L-phenylalanine has a molecular weight of 199.63 and a molecular formula of C9H10ClNO2. It is a non-proteinogenic L-alpha-amino acid. The compound should be stored at room temperature. It is soluble in appropriate solvents for research use. It is for research use only and is not intended for human consumption.
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| Toxicity/Toxicokinetics |
The toxicity profile of 4-Chloro-L-phenylalanine has not been extensively reported. As an inhibitor of serotonin synthesis, potential adverse effects may include depletion of serotonin, which could affect mood, sleep, appetite, and other serotonin-mediated functions. The compound is for research use only and is not intended for human consumption. Standard toxicological evaluation would include acute and repeated-dose toxicity studies.
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| References | |
| Additional Infomation |
4-Chloro-L-phenylalanine is a non-protein L-α-amino acid, a derivative of L-phenylalanine in which the hydrogen atom between the benzene rings is replaced by a chlorine atom. It is a chlorinated amino acid, belonging to the non-protein L-α-amino acid family, a monochlorobenzene compound, and a derivative of L-phenylalanine. Fenclonine is a selective and irreversible inhibitor of tryptophan hydroxylase, the rate-limiting enzyme in the biosynthesis of serotonin (5-hydroxytryptamine). The pharmacological action of fenclonine is to lower endogenous serotonin levels.
4-Chloro-L-phenylalanine (L-PCPA, CAS 14173-39-8) is a potent inhibitor of the enzyme tryptophan hydroxylase (TPH), which is involved in the biosynthesis of serotonin. It acts as a non-specific antagonist of both TPH1 and TPH2 isoforms. It is used to block serotonin synthesis in research studies. It is available for research purposes only. |
| Molecular Formula |
C9H10CLNO2
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| Molecular Weight |
199.63
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| Exact Mass |
199.04
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| CAS # |
14173-39-8
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| PubChem CID |
736190
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
339.5±32.0 °C at 760 mmHg
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| Melting Point |
235-238ºC
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| Flash Point |
159.1±25.1 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.590
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| LogP |
1.71
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
13
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| Complexity |
179
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=CC(=CC=C1C[C@@H](C(=O)O)N)Cl
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| InChi Key |
NIGWMJHCCYYCSF-QMMMGPOBSA-N
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| InChi Code |
InChI=1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1
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| Chemical Name |
(2S)-2-amino-3-(4-chlorophenyl)propanoic 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) |
H2O: 12.5 mg/mL (62.62 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 | 5.0093 mL | 25.0463 mL | 50.0927 mL | |
| 5 mM | 1.0019 mL | 5.0093 mL | 10.0185 mL | |
| 10 mM | 0.5009 mL | 2.5046 mL | 5.0093 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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