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L-Phenylalanine-13C9,15N ((S)-2-Amino-3-phenylpropionic acid-13C9,15N)

L-Phenylalanine-13C9,15N is L-Phenylalanine with a 13C label and a 15N label.
L-Phenylalanine-13C9,15N ((S)-2-Amino-3-phenylpropionic acid-13C9,15N)
L-Phenylalanine-13C9,15N ((S)-2-Amino-3-phenylpropionic acid-13C9,15N) Chemical Structure CAS No.: 878339-23-2
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
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10mg
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Other Forms of L-Phenylalanine-13C9,15N ((S)-2-Amino-3-phenylpropionic acid-13C9,15N):

  • L-Phenylalanine
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
L-Phenylalanine-13C9,15N is L-Phenylalanine with a 13C label and a 15N label. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid (AA) extracted from Escherichia coli. L-Phenylalanine is a voltage-dependent α2δ subunit Ca2+ channel antagonist (inhibitor) with a Ki of 980 nM. L-Phenylalanine is a competitive antagonist of the glycine and glutamate binding sites of NMDARs (KB 573 μM) and non-NMDARs. L-Phenylalanine is extensively used in the production of food flavors and pharmaceuticals.
L-Phenylalanine-13C9,15N is a fully stable isotope-labeled form of the essential amino acid L-phenylalanine, where all nine carbon atoms are replaced with the 13C isotope and the nitrogen atom is replaced with the 15N isotope (99 atom % enrichment for both). L-Phenylalanine is an aromatic, nonpolar amino acid that is one of the three amino acids capable of absorbing ultraviolet radiation above 250 nm. It is biologically converted into L-tyrosine, which in turn is converted to L-DOPA and further into the neurotransmitters dopamine, norepinephrine, and epinephrine. As a fully labeled compound, L-Phenylalanine-13C9,15N is chemically and biologically identical to natural L-phenylalanine but contains heavy isotopes that can be detected by mass spectrometry or NMR spectroscopy. This makes it a valuable tool for metabolic tracing studies, where it is used to track the metabolic fate of phenylalanine-derived carbon and nitrogen atoms in various biological systems. It is a top-tier tracer and quantitative standard for studying aromatic amino acid metabolism and related diseases. The compound is not a drug and has no approved clinical indications.
Biological Activity I Assay Protocols (From Reference)
Targets
NMDA Receptor
L-Phenylalanine-13C9,15N does not have a distinct pharmacological target separate from natural L-phenylalanine. L-Phenylalanine is an essential amino acid that serves as a precursor for the biosynthesis of L-tyrosine, which is further metabolized to L-DOPA, dopamine, norepinephrine, and epinephrine. L-Phenylalanine also acts as a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM) and non-NMDARs, respectively. In the context of L-Phenylalanine-13C9,15N as a stable isotope tracer, the compound targets the same metabolic and receptor pathways as unlabeled L-phenylalanine but is used primarily to study carbon and nitrogen metabolism rather than receptor pharmacology.
ln Vitro
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
As a stable isotope-labeled compound, L-Phenylalanine-13C9,15N does not exhibit pharmacological activity distinct from that of natural L-phenylalanine. L-Phenylalanine itself is an essential amino acid that is incorporated into proteins and serves as a precursor for the biosynthesis of L-tyrosine, which is further metabolized to L-DOPA, dopamine, norepinephrine, and epinephrine. The 13C and 15N labeling does not alter the biological activity of L-phenylalanine, as the isotopic substitution does not affect the compound's chemical reactivity or metabolic properties. Therefore, the in vitro activity of L-Phenylalanine-13C9,15N is identical to that of unlabeled L-phenylalanine. In cell culture studies, the labeled compound is used as a metabolic tracer to track the incorporation of carbon and nitrogen into cellular metabolites.
ln Vivo
In vivo, L-Phenylalanine-13C9,15N is used primarily as a metabolic tracer rather than a pharmacologically active compound. When administered to animals or human subjects, the 13C and 15N labels allow researchers to trace the metabolic fate of phenylalanine-derived carbon and nitrogen in various tissues and biological fluids. L-Phenylalanine is an essential amino acid that plays critical roles in protein synthesis and the biosynthesis of neurotransmitters. The compound has been used as a supplement in liquid growth culture of Nostoc species to study the involvement of the noc operon in NoA (nocuolin A) synthesis.
Enzyme Assay
In vitro enzyme/receptor binding assays for L-Phenylalanine-13C9,15N are typically not performed to evaluate receptor binding or enzyme inhibition, as the compound is used as a metabolic tracer rather than a pharmacological modulator. However, for reference, L-phenylalanine binding to NMDA receptors can be studied using radioligand binding assays. L-Phenylalanine-13C9,15N itself is not typically used in such assays due to its isotopic labeling being better suited for mass spectrometry-based detection.
Cell Assay
In vitro cell-based assays using L-Phenylalanine-13C9,15N typically involve the incubation of cultured cells with the labeled compound to study carbon and nitrogen metabolism. Cells are cultured in media containing the labeled phenylalanine, and after a designated incubation period, metabolites are extracted and analyzed by mass spectrometry to determine the incorporation of the 13C and 15N labels into various metabolites. This approach is used in stable isotope-resolved metabolomics to map metabolic pathways and quantify metabolic fluxes.
Animal Protocol
In vivo animal studies with L-Phenylalanine-13C9,15N typically involve the administration of the labeled compound to rodents or other model organisms via oral gavage or intravenous injection. Following administration, blood, tissues, and urine are collected at various time points, and the samples are analyzed by mass spectrometry to trace the metabolic fate of the labeled carbon and nitrogen. This approach is used to study whole-body amino acid metabolism, neurotransmitter biosynthesis, and the metabolic consequences of various diseases.
ADME/Pharmacokinetics
L-Phenylalanine-13C9,15N is not a drug and does not have pharmacokinetic properties distinct from those of natural L-phenylalanine. L-Phenylalanine is an essential amino acid that is absorbed from the gastrointestinal tract and distributed throughout the body. It is metabolized primarily in the liver, where it is hydroxylated to L-tyrosine by phenylalanine hydroxylase. The pharmacokinetic behavior of the labeled compound is identical to that of unlabeled L-phenylalanine.
Toxicity/Toxicokinetics
No specific toxicity data are publicly available for L-Phenylalanine-13C9,15N. As a stable isotope-labeled form of the essential amino acid L-phenylalanine, the compound is expected to have a low toxicity profile similar to that of natural L-phenylalanine. L-Phenylalanine is generally well-tolerated at physiological concentrations. However, individuals with phenylketonuria (PKU) cannot metabolize phenylalanine properly, and high levels can be toxic. The 13C and 15N labeling does not introduce any additional toxicity.
References

[1]. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-216.

Additional Infomation
L-Phenylalanine-13C9,15N is a fully stable isotope-labeled form of the essential amino acid L-phenylalanine, where all nine carbon atoms are replaced with 13C and the nitrogen atom is replaced with 15N. It is used as a metabolic tracer in stable isotope-resolved metabolomics and flux analysis experiments to study carbon and nitrogen metabolism. The compound is a top-tier tracer and quantitative standard for studying aromatic amino acid metabolism and related diseases. It is not a drug and has no approved clinical indications. The compound is strictly for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
13C9H1115NO2
Molecular Weight
175.12
Exact Mass
175.106
CAS #
878339-23-2
Related CAS #
L-Phenylalanine;63-91-2
PubChem CID
16217565
Appearance
White to off-white solid powder
Melting Point
270-275 °C(dec.)(lit.)
LogP
1.341
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
[13CH]1=[13CH][13CH]=[13C]([13CH]=[13CH]1)[13CH2][13C@@H]([13C](=O)O)[15NH2]
InChi Key
COLNVLDHVKWLRT-CMLFETTRSA-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-/m0/s1/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1,9+1,10+1
Chemical Name
(2S)-2-(15N)azanyl-3-((1,2,3,4,5,6-13C6)cyclohexatrienyl)(1,2,3-13C3)propanoic 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 Data
Solubility (In Vitro)
H2O: 20.83 mg/mL (118.95 mM)
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.7104 mL 28.5519 mL 57.1037 mL
5 mM 1.1421 mL 5.7104 mL 11.4207 mL
10 mM 0.5710 mL 2.8552 mL 5.7104 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.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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