PHENYLALANINE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H11NO2
Molecular Weight	165.1891
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CC1=CC=CC=C1)C(O)=O

InChI

InChIKey=COLNVLDHVKWLRT-QMMMGPOBSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.anaturalhealingcenter.com/documents/Thorne/monos/DLPA%20mono.pdf | http://www.cpmedical.net/pdf/Phenylalanine.pdf

Phenylalanine is a biologically essential amino acid that acts as a precursor to tyrosine and the catecholamines (epinephrine, norepinephrine, dopamine, and tyramine), and is a constituent of many central nervous system neuropeptides. Normal dietary levels of phenylalanine are approximately 1-2 grams daily. Phenylalanine appears in two forms which are identical mirror images of each other: L-phenylalanine, a nutritional supplement, and D-phenylalanine, an effective painkiller and antidepressant due to its ability to inhibit the breakdown of enkephalins, the brain’s natural pain killers.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phenylalanine-4-hydroxylase 9 Target ID: CHEMBL3076 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23457044 \| https://www.ncbi.nlm.nih.gov/pubmed/12056888	Substrate 656
Glutamate NMDA receptor 47 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12645085 \| https://www.ncbi.nlm.nih.gov/pubmed/11986979	Modulator 822		1.71 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Burns 17 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=016822	Primary	Approved 8360	FREAMINE III 10% Approved Use Parenteral nutrition with 8.5% FreAmine® III (Amino Acid Injection) with Electrolytes is indicated to prevent nitrogen loss or treat negative nitrogen balance in adults and pediatric patients, where (1) the alimentary tract, by the oral, gastrostomy, or jejunostomy route, cannot or should not be used, or adequate protein intake is not feasible by these routes; (2) gastrointestinal absorption of protein is impaired; or (3) protein requirements are substantially increased as with extensive burns. Dosage, route of administration, and concomitant infusion of non-protein calories are dependent on various factors, such as nutritional metabolic status of the patient, anticipated duration of parenteral nutritional support, and vein tolerance Launch Date 5.4345601E10
Pain 608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3524509 http://www.cpmedical.net/pdf/Phenylalanine.pdf http://www.anaturalhealingcenter.com/documents/Thorne/monos/DLPA%20mono.pdf	Primary	Not Provided 503	Unknown Approved Use Unknown
Depression 233 Sources: http://www.cpmedical.net/pdf/Phenylalanine.pdf http://www.anaturalhealingcenter.com/documents/Thorne/monos/DLPA%20mono.pdf	Primary	Not Provided 503	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1389 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11244252/	20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PHENYLALANINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
35.7 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11244252/	20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PHENYLALANINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11244252/	20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PHENYLALANINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
1.5 g single, oral Dose: 1.5 g Route: oral Route: single Dose: 1.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/3995775	healthy, 36 years Health Status: healthy Age Group: 36 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3995775	Sources: https://pubmed.ncbi.nlm.nih.gov/3995775
8.2 g single, intravenous (total) Highest studied dose Dose: 8.2 g Route: intravenous Route: single Dose: 8.2 g Sources: https://pubmed.ncbi.nlm.nih.gov/6853713/	healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6853713/	Sources: https://pubmed.ncbi.nlm.nih.gov/6853713/

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-024432	http://www.3bsc.com/index/pro_info.php?id=45508
AA Blocks	AA001M4O	http://www.aablocks.com/goods/Goods/detail?id=AA001M4O
AHH Chemical co.,ltd	MT-20988	http://www.ahhchemical.com/product/MT-20988.html
AHH Chemical co.,ltd	MT-20990	http://www.ahhchemical.com/product/MT-20990.html
AHH Chemical co.,ltd	NP-1146	http://www.ahhchemical.com/product/NP-1146.html
AK Scientific, Inc. (AKSCI)	K018	http://www.aksci.com/item_detail.php?cat=K018
Aaron Chemicals	AR001MWG	http://www.aaronchem.com/150-30-1
AbMole Bioscience	M5756	http://www.abmole.com/products/l-phenylalanine.html
Acadechem	ACDS-061590	http://www.acadechemical.com/product/136289
Acadechem	ACDS-070486	http://www.acadechemical.com/product/145185
Achemo Scientific Limited	AC-21868	http://www.achemo.com/product_view.asp?ID=11758
Achemo Scientific Limited	AC-23951	http://www.achemo.com/search/?Keyword= 63-91-2
Achemtek	0101-001283	http://www.achemtek.com/63-91-2
Acorn PharmaTech	ACN-033438	http://www.acornpharmatech.com/
Acros Organics	AC453930010	https://www.fishersci.com/shop/products/l-phenylalanine-98-5-101-0-acros-organics-2/AC453930010
Acros Organics	AC130315000	https://www.fishersci.com/shop/products/l-phenylalanine-98-5-acros-organics-2/AC130315000
Acros Organics	AC130310025	https://www.fishersci.com/shop/products/l-phenylalanine-98-5-acros-organics-3/AC130310025
Acros Organics	AC130310250	https://www.fishersci.com/shop/products/l-phenylalanine-98-5-acros-organics/AC130310250
Acros Organics	AC130311000	https://www.fishersci.com/shop/products/l-phenylalanine-98-5-acros-organics/AC130311000
Alfa Aesar	A13238	https://www.alfa.com/en/catalog/A13238/
Alfa Chemistry	AP63912	https://reagents.alfa-chemistry.com/product/l-phenylalanine-cas-63-91-2-14475.html
Alfa Chemistry	3617-44-5	https://www.alfa-chemistry.com/cas_3617-44-5.htm
Alfa Chemistry	67675-33-6	https://www.alfa-chemistry.com/cas_67675-33-6.htm
Alfa Chemistry	63-91-2	https://www.alfachemic.com/catalysts/l-phenylalanine-cas-63-91-2-item-321936.htm
Alfa Chemistry	ACM63912	https://www.alfachemic.com/catalysts/product/l-phenylalanine-cas-63-91-2-321936.html
Alichem	471003588	http://www.alichem.com/en/products/63-91-2.html
Allbio Pharm Co., Ltd	AD02774	http://www.allbiopharm.com/product/n/AD02774
Angene	AGN-PC-0Q5GWQ	http://www.angenechemical.com/productshow/AGN-PC-0Q5GWQ.html
Anward	ANW-34771	http://www.anward.com/pro_result/24935
ApexBio Technology	A6802	http://www.apexbt.com/h-phe-2-chlorotrityl-resin.html
ApexBio Technology	A7262	http://www.apexbt.com/h-phe-oh.html
Aurum Pharmatech LLC	M-5935	http://www.Aurumpharmatech.com/Product/ProductDetails/M_5935
Avantor Inc	101095-796	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101095-796
Avantor Inc	200000-766	https://us.vwr.com/store/product/7514882/l-phenylalanine-98-5
BioSynth	Q-201326	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-201326.html
BroadPharm	BP-20538	https://www.broadpharm.com/web/product.php?catalog=BP-20538
Capot Chemical	11004	http://www.capotchem.com/en/11004.htm
Capot Chemical	PubChem11004	http://www.capotchem.com/en/11004.htm
Chem Scene	CS-2315	http://www.chemscene.com/63-91-2.html
ChemFaces	CFN93152	http://www.chemfaces.com/natural/L-Phenylalanine-CFN93152.html
ChemMol	1030004	http://www.chemmol.com/chemmol/1030004.html
ChemMol	30114488	http://www.chemmol.com/chemmol/30114488.html
ChemMol	30201376	http://www.chemmol.com/chemmol/30201376.html
ChemMol	44010152	http://www.chemmol.com/chemmol/44010152.html
ChemMol	49405040	http://www.chemmol.com/chemmol/49405040.html
Chemenu	CM119307	http://www.chemenu.com/products/CM119307
Chemspace	CSSB00011417287	https://chem-space.com/CSSB00011417287
China MainChem Co., Ltd	MC-22839-47-0	https://www.mainchem.com/product/aspartame/
China MainChem Co., Ltd	MS63-91-2	https://www.mainchem.com/product/l-phenylalanine/
Chiralblock Biosciences	CB10638	http://www.chiralblock.com/products/63-91-2.html
DC Chemicals	DCB-074	http://www.dcchemicals.com//product_show-L_Phenylalanine.html
Debye Scientific	DB-029978	http://www.debyesci.com/DB-029978.html
Enamine	Z1258578341	https://www.enaminestore.com/catalog/Z1258578341
Glentham Life Sciences	GM4385	http://www.glentham.com/products/product/GM4385/
Hairui	HR123548	http://www.hairuichem.com/en/product/150-30-1.html
Hairui	HR123017	http://www.hairuichem.com/en/product/63-91-2.html
LGC Standards	DRE-C16055100	https://www.lgcstandards.com/US/en/p/DRE-C16055100
LGC Standards	LGCFOR1560.00	https://www.lgcstandards.com/US/en/p/LGCFOR1560.00
LGC Standards	MM1560.00	https://www.lgcstandards.com/US/en/p/MM1560.00
Lab Network	LN00173955	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00173955
Matrix Scientific	75335	https://www.matrixscientific.com/075335.html
MedChem Express	HY-N0215	https://www.medchemexpress.com/L-Phenylalanine.html
MuseChem	I004417	https://www.musechem.com/product/I004417.html
MuseChem	M118591	https://www.musechem.com/product/M118591.html
OChem	4802	http://www.ocheminc.com/index.php?act=psearch&pid=63P912
Oakwood	M02961	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=127765&ExtHyperLink=1
Oakwood	404464	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=195112&ExtHyperLink=1
Parchem	946	http://www.parchem.com/chemical-supplier-distributor/L-Phenylalanine-001987.aspx
Renno Tech	RP22791	http://www.rennotech.com/product_show.asp?id=28480
Renno Tech	RP22792	http://www.rennotech.com/product_show.asp?id=28481
Renno Tech	RP22793	http://www.rennotech.com/product_show.asp?id=28482
Sigma-Aldrich	24-1640_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/241640?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	40541_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/40541?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	91331_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/91331?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	78019_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/78019?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1530503_USP	https://www.sigmaaldrich.com/catalog/product/usp/1530503?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S045933	http://www.sinfoobiotech.com/product/1049331
Sinfoo Biotech	S054829	http://www.sinfoobiotech.com/product/1058227
Smolecule	S793363	https://www.smolecule.com/products/s793363
Synblock Inc	AB02575	http://www.synblock.com/product/63-91-2.html
TCI (Tokyo Chemical Industry)	P0134	http://www.tcichemicals.com/eshop/en/us/commodity/P0134/index.html
VladaChem	VL143776	https://www.vladachem.com/product.php?products=63-91-2
VladaChem	VL164263	https://www.vladachem.com/product.php?products=63-91-2
VladaChem	VL264615-100G	https://www.vladachem.com/product.php?products=63-91-2
Watanabe Chemical Ind.	G00029	https://www.watanabechem.co.jp/en/search/details.php?code=G00029
abcr GmbH	AB118462	http://www.abcr.com/shop/en/AB118462
abcr GmbH	AB354874	http://www.abcr.com/shop/en/AB354874
eNovation Chemicals	D380463	http://www.enovationchem.com/productDetails.asp?productID=D380463
eNovation Chemicals	D606846	https://enovationchem.com/ProductDetails.asp?ProductID=D606846
eNovation Chemicals	K47598	https://www.enovationchem.com/ProductDetails.asp?ProductID=K47598
iChemical	EBD2198134	http://www.ichemical.com/products/63-91-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-5960921520	https://mcule.com/MCULE-5960921520/

PubMed

Title	Date	PubMed
Development of procedures for determining the amino acid requirements of chickens by the indicator amino acid oxidation method.	2001 Feb	11233006
Detection and typing of human papillomavirus in anal epidermoid carcinomas: sequence variation in the E7 gene of human papillomavirus Type 16.	2001 Feb	11227941
Comparison of in vitro systems of protein digestion using either mammal or fish proteolytic enzymes.	2001 Feb	11223397
Mutation analysis of phenylketonuria in Yamagata prefecture, Japan.	2001 Feb	11207989
Reaction of oxidized dopamine with endogenous cysteine residues in the human dopamine transporter.	2001 Feb	11181843
Auto-inhibition of Ca(2+)/calmodulin-dependent protein kinase II by its ATP-binding domain.	2001 Feb	11181826
Mutations of the phenylalanine hydroxylase (PAH) gene in Brazilian patients with phenylketonuria.	2001 Feb	11180595
A comparison of kinetic and regulatory properties of the tetrameric and dimeric forms of wild-type and Thr427-->Pro mutant human phenylalanine hydroxylase: contribution of the flexible hinge region Asp425-Gln429 to the tetramerization and cooperative substrate binding.	2001 Feb	11179966
Pumping capacity of bacterial reaction centers and backpressure regulation of energy transduction.	2001 Feb	11179962
Design, X-ray crystallography, molecular modelling and thermal stability studies of mutant enzymes at site 172 of 3-isopropylmalate dehydrogenase from Thermus thermophilus.	2001 Feb	11173468
[A study of phenylketonuria heterozygotes screening in married population of Tianjin area].	2001 Feb	11172645
Tyrosine phosphorylation of p120(ctn) in v-Src transfected L cells depends on its association with E-cadherin and reduces adhesion activity.	2001 Feb	11171320
Aldehyde dehydrogenase. Maintaining critical active site geometry at motif 8 in the class 3 enzyme.	2001 Feb	11168411
In vitro expression of 34 naturally occurring mutant variants of phenylalanine hydroxylase: correlation with metabolic phenotypes and susceptibility toward protein aggregation.	2001 Feb	11161839
Stimulation of human albumin synthesis and gene expression by growth hormone treatment.	2001 Feb	11161545
Implicit solvent model studies of the interactions of the influenza hemagglutinin fusion peptide with lipid bilayers.	2001 Feb	11159433
Whole body and skeletal muscle glutamine metabolism in healthy subjects.	2001 Feb	11158937
American Academy of Pediatrics: Maternal phenylketonuria.	2001 Feb	11158484
Effects of the potent analgesic enkephalin-catabolizing enzyme inhibitors RB101 and kelatorphan on respiration.	2001 Feb 1	11166965
Site-directed mutagenesis of human immunodeficiency virus type 1 reverse transcriptase at amino acid position 138.	2001 Feb 1	11162823
Enkephalin analogues with 2',6'-dimethylphenylalanine replacing phenylalanine in position 4.	2001 Feb 12	11212102
FDA approves nateglinide for treatment of type 2 diabetes.	2001 Feb 15	11225164
Antioxidant alpha-lipoic acid and protein turnover in insulin-resistant rat muscle.	2001 Feb 15	11182293
Cloning of dopamine, norepinephrine and serotonin transporters from monkey brain: relevance to cocaine sensitivity.	2001 Feb 19	11223167
Occurrence of D-Amino Acids and a pyridoxal 5'-phosphate-dependent aspartate racemase in the acidothermophilic archaeon, Thermoplasma acidophilum.	2001 Feb 23	11181048
Altered mitochondrial gene expression in human gestational trophoblastic diseases.	2001 Feb-Mar	11170827
The suppressive effect of dietary restriction and weight loss in the obese on the generation of reactive oxygen species by leukocytes, lipid peroxidation, and protein carbonylation.	2001 Jan	11232024
Three new mutations in the gene for the growth hormone (gh)-releasing hormone receptor in familial isolated gh deficiency type ib.	2001 Jan	11232012
A silent mutation induces exon skipping in the phenylalanine hydroxylase gene in phenylketonuria.	2001 Jan	11214902
N-(Hydroxyaminocarbonyl)phenylalanine: a novel class of inhibitor for carboxypeptidase A.	2001 Jan	11197339
Mealtime glucose regulation with nateglinide in healthy volunteers: comparison with repaglinide and placebo.	2001 Jan	11194245
Physical stability of the blue pigments formed from geniposide of gardenia fruits: effects of pH, temperature, and light.	2001 Jan	11170609
A matrix metalloproteinase inhibitor, batimastat, retards the development of osteolytic bone metastases by MDA-MB-231 human breast cancer cells in Balb C nu/nu mice.	2001 Jan	11165137
Characterization of the mouse phenylalanine hydroxylase mutation Pah(enu3).	2001 Jan	11161825
Tryptophan fluorescence of yeast actin resolved via conserved mutations.	2001 Jan	11159413
[Fasting blood glucose has little value. Postprandial glucose indicates risk].	2001 Jan 11	11216017
Biological properties of Phe(o)-opioid peptide analogues.	2001 Jan 12	11213367
Development and de novo protein synthetic activity of bovine embryos produced in vitro in different culture systems.	2001 Jan 15	11233785
Essential role of the N-terminal autoregulatory sequence in the regulation of phenylalanine hydroxylase.	2001 Jan 19	11163771
Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue.	2001 Mar	11237944
Binding diversity of a noncovalent-type low-molecular-weight serine protease inhibitor and function of a catalytic water molecule: X-ray crystal structure of PKSI-527--inhibited trypsin.	2001 Mar	11226886
Combined pituitary hormone deficiency due to the F135C human Pit-1 (pituitary-specific factor 1) gene mutation: functional and structural correlates.	2001 Mar	11222742
Ligand migration in human myoglobin: steric effects of isoleucine 107(G8) on O(2) and CO binding.	2001 Mar	11222311
Acute effects of peritoneal dialysis with dialysates containing dextrose or dextrose and amino acids on muscle protein turnover in patients with chronic renal failure.	2001 Mar	11181804
Selected Contribution: IGF-I antibody prevents increases in protein synthesis in epitrochlearis muscles from refed, diabetic rats.	2001 Mar	11181633
A possible role for metalloproteinases in renal cyst development.	2001 Mar	11181417
Complete loss of P/Q calcium channel activity caused by a CACNA1A missense mutation carried by patients with episodic ataxia type 2.	2001 Mar	11179022
Detection of hydroxyl radicals by D-phenylalanine hydroxylation: a specific assay for hydroxyl radical generation in biological systems.	2001 Mar 1	11180947
Activation of BMK1 via tyrosine 1062 in RET by GDNF and MEN2A mutation.	2001 Mar 2	11237712
Tight control of exogenous SERCA expression is required to obtain acceleration of calcium transients with minimal cytotoxic effects in cardiac myocytes.	2001 Mar 2	11230109

Patents

Sample Use Guides

In Vivo Use Guide

L-Phenylalanine Capsules (400 mg/cap): one to two capsules per day on an empty stomach. L-Phenylalanine Powder: 480 mg one to two times per day on an empty stomach. DL-Phenylalanine Capsules (500 mg/cap): one capsule daily on an empty stomach. DL-Phenylalanine Powder: 1/8 level teaspoon two to three times daily on an empty stomach.

Route of Administration: Oral

In Vitro Use Guide

In cultured hippocampal neurons from newborn rats L-phenylalanine specifically and reversibly attenuated NMDA-activated currents in a concentration-dependent manner (IC50=1.71 mM)

Name

Type

Language

PHENYLALANINE

Official Name

English

L-PHENYLALANINE [USP-RS]

Common Name

English

LEUCINE IMPURITY C [EP IMPURITY]

Common Name

English

NSC-79477

Code

English

TYROSINE IMPURITY A [EP IMPURITY]

Common Name

English

FEMA NO. 3585

Code

English

NATEGLINIDE IMPURITY D [EP IMPURITY]

Common Name

English

Phenylalanine [WHO-DD]

Common Name

English

3-PHENYL-L-ALANINE

Systematic Name

English

PHENYLALANINE [VANDF]

Common Name

English

PHENYLALANINE [INCI]

Common Name

English

phenylalanine [INN]

Common Name

English

PHENYLALANINE [MI]

Common Name

English

L-PHENYLALANINE

Systematic Name

English

L-.ALPHA.-AMINO-.BETA.-PHENYLPROPIONIC ACID

Common Name

English

PHENYLALANINE [HSDB]

Common Name

English

LYSINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]

Common Name

English

PHENYLALANINE [MART.]

Common Name

English

L-PHENYLALANINE [FHFI]

Common Name

English

LAEVO-PHENYL ALANINE

Common Name

English

(2S)-2-AMINO-3-PHENYLPROPANOIC ACID

Systematic Name

English

PHENYLALANINE [USAN]

Common Name

English

L-PHENYLALANINE [JAN]

Common Name

English

PHENYLALANINE [EP MONOGRAPH]

Common Name

English

PHENYLALANINE [II]

Common Name

English

PHENYLALANINE [USP MONOGRAPH]

Common Name

English

L-PHENYLALANINE [FCC]

Common Name

English

Classification Tree Code System Code

LOINC

53396-8