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

Molecular Formula	C9H11NO2
Molecular Weight	165.1891
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 643
Glutamate NMDA receptor 45 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12645085 \| https://www.ncbi.nlm.nih.gov/pubmed/11986979	Modulator 817		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 8307	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 607 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 505	Unknown Approved Use Unknown
Depression 232 Sources: http://www.cpmedical.net/pdf/Phenylalanine.pdf http://www.anaturalhealingcenter.com/documents/Thorne/monos/DLPA%20mono.pdf	Primary	Not Provided 505	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
Cloning and functional expression of a human Na(+) and Cl(-)-dependent neutral and cationic amino acid transporter B(0+).	1999 Aug 20	10446133
L-amino acid sensing by the extracellular Ca2+-sensing receptor.	2000 Apr 25	10781086
Association between minihaplotypes and mutations at the PAH locus in Polish hyperphenylalaninemic patients.	2001	11096279
Further definition of the substance P (SP)/neurokinin-1 receptor complex. MET-174 is the site of photoinsertion p-benzoylphenylalanine4 SP.	2001 Apr 6	11116140
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
In vitro expression of 34 naturally occurring mutant variants of phenylalanine hydroxylase: correlation with metabolic phenotypes and susceptibility toward protein aggregation.	2001 Feb	11161839
Whole body and skeletal muscle glutamine metabolism in healthy subjects.	2001 Feb	11158937
American Academy of Pediatrics: Maternal phenylketonuria.	2001 Feb	11158484
Conserved transmembrane tyrosine residues of the TCR beta chain are required for TCR expression and function in primary T cells and hybridomas.	2001 Feb	11157854
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
Antioxidant alpha-lipoic acid and protein turnover in insulin-resistant rat muscle.	2001 Feb 15	11182293
C-terminal elements control location, activation threshold, and p38 docking of ribosomal S6 kinase B (RSKB).	2001 Feb 23	11035004
Development of matrix metalloproteinase inhibitors in cancer therapy.	2001 Feb 7	11158186
Kynurenine aminotransferase I activity in human placenta.	2001 Feb-Mar	11170833
Altered mitochondrial gene expression in human gestational trophoblastic diseases.	2001 Feb-Mar	11170827
A silent mutation induces exon skipping in the phenylalanine hydroxylase gene in phenylketonuria.	2001 Jan	11214902
Mealtime glucose regulation with nateglinide in healthy volunteers: comparison with repaglinide and placebo.	2001 Jan	11194245
New analogues of bradykinin containing a conformationally restricted dipeptide fragment in their molecules.	2001 Jan	11168884
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
Beta-adrenoceptor stimulation attenuates the hypertrophic effect of alpha-adrenoceptor stimulation in adult rat ventricular cardiomyocytes.	2001 Jan	11153756
Chronic maternal smoking and cord blood amino acid and enzyme levels at term.	2001 Jan	11152908
Net amino acid flux across the fetal liver and placenta during spontaneous ovine parturition.	2001 Jan	11150831
The protein-retaining effects of growth hormone during fasting involve inhibition of muscle-protein breakdown.	2001 Jan	11147801
Preparative HPLC resolution of the CIS cyclohexane analogs of phenylalanine.	2001 Jan	11135415
The effect of graded intake of glycyl-L-tyrosine on phenylalanine and tyrosine metabolism in parenterally fed neonates with an estimation of tyrosine requirement.	2001 Jan	11134500
Serine 187 is a crucial residue for allosteric regulation of Corynebacterium glutamicum 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase.	2001 Jan 1	11150666
Tyrosine phosphorylation of the beta 4 integrin cytoplasmic domain mediates Shc signaling to extracellular signal-regulated kinase and antagonizes formation of hemidesmosomes.	2001 Jan 12	11044453
Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue.	2001 Mar	11237944
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
A possible role for metalloproteinases in renal cyst development.	2001 Mar	11181417
Detection of hydroxyl radicals by D-phenylalanine hydroxylation: a specific assay for hydroxyl radical generation in biological systems.	2001 Mar 1	11180947
Spectral and metal-binding properties of three single-point tryptophan mutants of the human transferrin N-lobe.	2001 Mar 1	11171122
Essential tyrosine residues for interaction of the non-receptor protein-tyrosine phosphatase PTP1B with N-cadherin.	2001 Mar 2	11106648
A novel adapter protein employs a phosphotyrosine binding domain and exceptionally basic N-terminal domains to capture and localize an atypical protein kinase C: characterization of Caenorhabditis elegans C kinase adapter 1, a protein that avidly binds protein kinase C3.	2001 Mar 30	11134024
Crystallographic and solution studies of an activation loop mutant of the insulin receptor tyrosine kinase: insights into kinase mechanism.	2001 Mar 30	11124964
Renal matrix metalloproteinase activity is unaffected by experimental ischemia-reperfusion injury and matrix metalloproteinase inhibition does not alter outcome of renal function.	2001 Mar-Apr	11150860

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)

Substance Class	Chemical Created by `admin` on `Fri Dec 16 16:11:27 UTC 2022` Edited by `admin` on `Fri Dec 16 16:11:27 UTC 2022`
Record UNII	47E5O17Y3R
Record Status	`Validated (UNII)`
Record Version

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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