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| Other Sizes |
| Targets |
DL-3-Phenylalanine does not have a single defined primary drug target. As a precursor to the neurotransmitters dopamine, norepinephrine, and epinephrine, its effects are mediated through the modulation of catecholaminergic signaling pathways. L-Phenylalanine is converted to L-tyrosine, which is then converted to L-DOPA and subsequently to dopamine, norepinephrine, and epinephrine. D-Phenylalanine may inhibit the enzyme enkephalinase, thereby increasing levels of endogenous enkephalins, which are involved in pain modulation. However, the racemic mixture's overall activity is complex and involves multiple pathways.
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| ln Vitro |
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro activity of DL-3-Phenylalanine is related to its role as a precursor for neurotransmitter synthesis and as a component of ergogenic supplements. Amino acid derivatives like DLPA have been commercially used to affect the release of anabolic hormones, the availability of fuel for activity, and the ability to think clearly under pressure. In cell-based assays, phenylalanine can be taken up by cells and metabolized to tyrosine, influencing cellular catecholamine levels. However, the specific in vitro activity of the racemic mixture has not been extensively characterized beyond its metabolic fate and its use as a nutritional supplement. |
| ln Vivo |
In vivo activity of DL-3-Phenylalanine has been studied for its potential effects on mood, pain, and cognitive function. As a precursor to catecholamines, it may influence neurotransmitter levels in the brain. D-Phenylalanine's inhibition of enkephalinase may contribute to analgesic effects. DLPA has been investigated in clinical studies for its potential benefits in depression, chronic pain, and Parkinson's disease. However, the evidence for its efficacy is mixed, and it is not approved as a drug for these indications. It is primarily used as a dietary supplement.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for DL-3-Phenylalanine could focus on its interactions with enzymes involved in neurotransmitter synthesis or degradation. For example, the activity of phenylalanine hydroxylase, which converts phenylalanine to tyrosine, could be measured in the presence of the compound. Additionally, the inhibition of enkephalinase by D-phenylalanine could be assessed using a fluorogenic substrate. These assays would help elucidate the compound's mechanism of action at the molecular level.
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| Cell Assay |
Cell-based assays for DL-3-Phenylalanine could involve measuring its effects on neurotransmitter synthesis in neuronal cell lines. For example, PC12 cells or other catecholaminergic cells could be treated with DLPA, and the levels of dopamine, norepinephrine, and their metabolites could be measured using HPLC or ELISA. This assay would directly assess the compound's ability to influence neurotransmitter production in a cellular context.
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| Animal Protocol |
In vivo animal experiments for DL-3-Phenylalanine have been conducted in various models. For example, in rodent models of depression, DLPA has been tested for its antidepressant-like effects using the forced swim test or tail suspension test. In pain models, such as the hot plate test or formalin test, its analgesic effects have been evaluated. These experiments help determine the compound's potential therapeutic applications in mood disorders and pain management.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of DL-3-Phenylalanine have been studied as it is a naturally occurring amino acid. It is absorbed from the gastrointestinal tract via amino acid transporters and distributed throughout the body. It crosses the blood-brain barrier via the large neutral amino acid transporter (LAT1). Phenylalanine is metabolized primarily in the liver by phenylalanine hydroxylase to tyrosine. The half-life of phenylalanine in plasma is approximately 1-2 hours. However, the pharmacokinetics of the racemic mixture may differ slightly from the individual enantiomers.
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| Toxicity/Toxicokinetics |
The toxicity profile of DL-3-Phenylalanine is generally considered to be low, as it is a naturally occurring amino acid. However, high doses can lead to elevated phenylalanine levels, which may be problematic for individuals with phenylketonuria (PKU), a genetic disorder that impairs phenylalanine metabolism. In healthy individuals, excessive intake may cause side effects such as nausea, heartburn, and headache. Chronic toxicity and carcinogenicity studies have not been extensively conducted for the racemic mixture.
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| References | |
| Additional Infomation |
Phenylalanine is an aromatic amino acid, formed by replacing one methyl hydrogen atom of alanine with a phenyl group. It is a metabolite of the large flea (Daphnia magna). It is an α-amino acid and also an aromatic amino acid. It contains a benzyl group. It is both the conjugate base and conjugate acid of phenylalanine. DL-phenylalanine has been reported to exist in Atractylodes japonica, soybean (Glycine max), and other organisms with relevant data. DL-phenylalanine is a racemic mixture of phenylalanine, an aromatic amino acid with antidepressant, analgesic, and appetite-suppressing effects. The antidepressant effect of DL-phenylalanine may be related to its precursor role in the synthesis of the neurotransmitters norepinephrine and dopamine. Elevated levels of norepinephrine and dopamine in the brain are thought to be associated with antidepressant effects. This medication also helps alleviate mood swings associated with premenstrual syndrome (PMS), improves energy and mental alertness, and enhances focus in patients with attention deficit hyperactivity disorder (ADHD).
See also: Phenylalanine (note moved to). DL-3-Phenylalanine (DLPA) is a racemic mixture of phenylalanine enantiomers used as a research chemical and dietary supplement. It is not a drug and has no approved therapeutic indications. It has been investigated for its potential benefits in mood disorders, pain management, and cognitive enhancement. The compound is commercially available from various suppliers for research purposes. Its primary applications are in nutritional science and pharmacology research. It is also known as 2-amino-3-phenylpropionic acid. |
| Molecular Formula |
C9H11NO2
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|---|---|
| Molecular Weight |
165.19
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| Exact Mass |
165.078
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| CAS # |
150-30-1
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| Related CAS # |
DL-3-Phenylalanine-d8;29909-00-0;DL-3-Phenylalanine-13C-1;64193-01-7;DL-3-Phenylalanine-15N;81387-53-3;DL-3-Phenylalanine-13C;286425-42-1;DL-3-Phenylalanine-d2;74228-83-4;DL-3-Phenylalanine-d;14246-24-3
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| PubChem CID |
994
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
307.5±30.0 °C at 760 mmHg
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| Melting Point |
266-267ºC
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| Flash Point |
139.8±24.6 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.576
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| LogP |
1.11
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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 |
12
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| Complexity |
153
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C(C([H])(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])N([H])[H])=O
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| InChi Key |
COLNVLDHVKWLRT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)
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| Chemical Name |
2-amino-3-phenylpropanoic 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) |
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 | 6.0536 mL | 30.2682 mL | 60.5364 mL | |
| 5 mM | 1.2107 mL | 6.0536 mL | 12.1073 mL | |
| 10 mM | 0.6054 mL | 3.0268 mL | 6.0536 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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