| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Human Endogenous Metabolite
D-Phenylalanine targets carboxypeptidase A, endorphinase, and enkephalinase enzymes. By inhibiting these enzymes, it prevents the breakdown of endogenous endorphins and enkephalins, thereby prolonging their analgesic effects. It may also interact with the neurokinin-1 (NK-1) receptor as part of substance P analogues. |
|---|---|
| ln Vitro |
In vitro, D-phenylalanine and its analogues have demonstrated antiproliferative actions against small-cell lung cancer (SCLC) and non-small-cell lung cancer (NSCLC) cell lines. The [D-Arg(1), D-Phe(5), D-Trp(7,9), Leu(11)] substance P analogue exerts antiproliferative effects on human H-69 SCLC and COR-L23 NSCLC cell lines through the NK-1 receptor. D-Phenylalanine-substituted bradykinin analogues also stimulate calcium efflux in human lung fibroblasts.
|
| ln Vivo |
In vivo, D-phenylalanine is used for its analgesic properties through the enhancement of endogenous endorphin and enkephalin activity. It is administered orally as a dietary supplement for chronic pain management and mood support. The compound is generally well-tolerated, though high doses may cause headaches or gastrointestinal discomfort.
|
| Enzyme Assay |
In vitro enzyme assays for D-phenylalanine typically measure the inhibition of carboxypeptidase A, endorphinase, and enkephalinase activities. The compound is incubated with the enzyme and a suitable substrate, and the product formation is monitored spectrophotometrically or by chromatographic methods. The IC50 values for enzyme inhibition are determined to assess the potency of D-phenylalanine.
|
| Cell Assay |
In vitro cell experiments with D-phenylalanine involve treating cancer cell lines such as H-69 SCLC and COR-L23 NSCLC to study its antiproliferative effects. Cells are cultured with varying concentrations of D-phenylalanine or its analogues, and cell viability, proliferation, and apoptosis are assessed using MTT assays, flow cytometry, or other methods. The involvement of the NK-1 receptor is confirmed using competition assays with substance P.
|
| Animal Protocol |
In vivo animal experiments with D-phenylalanine typically involve animal models of pain, such as the tail-flick or hot-plate tests. The compound is administered orally or intraperitoneally, and pain thresholds are measured to assess its analgesic effects. Animal models of cancer may also be used to study the antitumor activity of D-phenylalanine-containing substance P analogues.
|
| ADME/Pharmacokinetics |
D-Phenylalanine is administered orally as a dietary supplement. It is absorbed from the gastrointestinal tract and distributed throughout the body. As a D-amino acid, it is metabolized differently from L-phenylalanine and may have a longer half-life due to slower enzymatic degradation. The compound is soluble in methanol and water and has a melting point of 273-276°C.
|
| Toxicity/Toxicokinetics |
D-Phenylalanine is generally well-tolerated at recommended doses. High doses may cause headaches or gastrointestinal discomfort. No severe toxicity has been reported in humans. However, comprehensive toxicological studies are limited. The compound is not recommended for use in patients with phenylketonuria due to the potential for phenylalanine accumulation.
|
| References | |
| Additional Infomation |
D-Phenylalanine occurs as needle-like or prismatic crystals. (NTP, 1992)
D-Phenylalanine is the D-enantiomer of phenylalanine. It is a phenylalanine and also a D-α-amino acid. It is the conjugate base of D-phenylalanine. It is the conjugate acid of D-phenylalanine. It is the enantiomer of L-phenylalanine. It is the zwitterion tautomer of D-phenylalanine. D-Phenylalanine is found in or produced by Escherichia coli (K12 strain, MG1655 strain). D-Phenylalanine has also been reported in Cyperus rotundus, Daphnia frenulum, and other organisms with relevant data. D-Phenylalanine is the synthetic dextrorotatory isomer of phenylalanine, an essential amino acid with antidepressant and analgesic activities. D-phenylalanine can be converted into tyrosine, which in turn can be converted into levodopa, norepinephrine, and epinephrine—all important neurotransmitters. Therefore, this drug is associated with elevated levels of dopamine and norepinephrine in the brain, which may help alleviate depressive symptoms. Furthermore, as an inhibitor of endorphinase (an enzyme that metabolizes endorphins), D-phenylalanine can treat chronic pain by blocking the breakdown of endorphins (natural pain relievers). D-Phenylalanine is a research compound with applications in pain management, cancer research, and pharmaceutical synthesis. It has been studied for its antidepressant and analgesic activities. No FDA-approved therapeutic indications exist for D-phenylalanine as a drug, but it is available as a dietary supplement. Its mechanism of action involves the inhibition of enzymes that degrade endogenous opioids, thereby enhancing pain relief. |
| Molecular Formula |
C9H11NO2
|
|---|---|
| Molecular Weight |
165.19
|
| Exact Mass |
165.078
|
| CAS # |
673-06-3
|
| Related CAS # |
D-Phenylalanine-d5;362049-55-6;D-Phenylalanine-d8;1202064-02-5
|
| PubChem CID |
71567
|
| Appearance |
White to off-white solid powder
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
307.5±30.0 °C at 760 mmHg
|
| Melting Point |
541 to 543 °F (Decomposes) (NTP, 1992)
|
| Flash Point |
139.8±24.6 °C
|
| Vapour Pressure |
0.0±0.7 mmHg at 25°C
|
| Index of Refraction |
1.576
|
| LogP |
1.11
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
12
|
| Complexity |
153
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C1=CC=C(C=C1)C[C@H](C(=O)O)N
|
| InChi Key |
COLNVLDHVKWLRT-MRVPVSSYSA-N
|
| 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)/t8-/m1/s1
|
| Chemical Name |
(2R)-2-amino-3-phenylpropanoic acid
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
H2O: 4.17 mg/mL (25.24 mM)
DMSO: 1 mg/mL (6.05 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2 mg/mL (12.11 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).
(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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