U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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 of Phenylalanine

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

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1971
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1389 μM
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

AUC

ValueDoseCo-administeredAnalytePopulation
35.7 μM × h
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 min
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

Doses

DosePopulationAdverse events​
1.5 g single, oral
Dose: 1.5 g
Route: oral
Route: single
Dose: 1.5 g
Sources:
healthy, 36 years
Health Status: healthy
Age Group: 36 years
Sex: M
Sources:
8.2 g single, intravenous
Highest studied dose
Dose: 8.2 g
Route: intravenous
Route: single
Dose: 8.2 g
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: M
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cloning and functional expression of a human Na(+) and Cl(-)-dependent neutral and cationic amino acid transporter B(0+).
1999 Aug 20
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
2000 Apr 25
Ten novel mutations in the phenylalanine hydroxylase gene (PAH) observed in Brazilian patients with phenylketonuria.
2001
Association between minihaplotypes and mutations at the PAH locus in Polish hyperphenylalaninemic patients.
2001
Self-association of the H3 region of syntaxin 1A. Implications for intermediates in SNARE complex assembly.
2001 Apr 20
Disruption of an active site hydrogen bond converts human heme oxygenase-1 into a peroxidase.
2001 Apr 6
Development of procedures for determining the amino acid requirements of chickens by the indicator amino acid oxidation method.
2001 Feb
Detection and typing of human papillomavirus in anal epidermoid carcinomas: sequence variation in the E7 gene of human papillomavirus Type 16.
2001 Feb
Comparison of in vitro systems of protein digestion using either mammal or fish proteolytic enzymes.
2001 Feb
Whole body and skeletal muscle glutamine metabolism in healthy subjects.
2001 Feb
American Academy of Pediatrics: Maternal phenylketonuria.
2001 Feb
Conserved transmembrane tyrosine residues of the TCR beta chain are required for TCR expression and function in primary T cells and hybridomas.
2001 Feb
Site-directed mutagenesis of human immunodeficiency virus type 1 reverse transcriptase at amino acid position 138.
2001 Feb 1
FDA approves nateglinide for treatment of type 2 diabetes.
2001 Feb 15
Antioxidant alpha-lipoic acid and protein turnover in insulin-resistant rat muscle.
2001 Feb 15
Cloning of dopamine, norepinephrine and serotonin transporters from monkey brain: relevance to cocaine sensitivity.
2001 Feb 19
Enhancement, relaxation, and reversal of the stereoselectivity for phosphotriesterase by rational evolution of active site residues.
2001 Feb 6
Development of matrix metalloproteinase inhibitors in cancer therapy.
2001 Feb 7
Critical role of the residue size at position 87 in H2O2- dependent substrate hydroxylation activity and H2O2 inactivation of cytochrome P450BM-3.
2001 Feb 9
Kynurenine aminotransferase I activity in human placenta.
2001 Feb-Mar
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
Three new mutations in the gene for the growth hormone (gh)-releasing hormone receptor in familial isolated gh deficiency type ib.
2001 Jan
A silent mutation induces exon skipping in the phenylalanine hydroxylase gene in phenylketonuria.
2001 Jan
Physical stability of the blue pigments formed from geniposide of gardenia fruits: effects of pH, temperature, and light.
2001 Jan
New analogues of bradykinin containing a conformationally restricted dipeptide fragment in their molecules.
2001 Jan
Epidermal H(2)O(2) accumulation alters tetrahydrobiopterin (6BH4) recycling in vitiligo: identification of a general mechanism in regulation of all 6BH4-dependent processes?
2001 Jan
Tryptophan fluorescence of yeast actin resolved via conserved mutations.
2001 Jan
Beta-adrenoceptor stimulation attenuates the hypertrophic effect of alpha-adrenoceptor stimulation in adult rat ventricular cardiomyocytes.
2001 Jan
Chronic maternal smoking and cord blood amino acid and enzyme levels at term.
2001 Jan
The unique tryptophan residue of the vitamin D receptor is critical for ligand binding and transcriptional activation.
2001 Jan
A study of peptide--peptide interaction by matrix-assisted laser desorption/ionization.
2001 Jan
Single-stranded DNA intermediates in IS91 rolling-circle transposition.
2001 Jan
Increasing the thermal stability of euphauserase. A cold-active and multifunctional serine protease from Antarctic krill.
2001 Jan
Ligand binding to integrin alpha(v)beta(3) requires tyrosine 178 in the alpha(v) subunit.
2001 Jan 1
[Fasting blood glucose has little value. Postprandial glucose indicates risk].
2001 Jan 11
Biological properties of Phe(o)-opioid peptide analogues.
2001 Jan 12
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
Development and de novo protein synthetic activity of bovine embryos produced in vitro in different culture systems.
2001 Jan 15
Haem-linked interactions in horseradish peroxidase revealed by spectroscopic analysis of the Phe-221-->Met mutant.
2001 Jan 15
Molecular engineering of myoglobin: the improvement of oxidation activity by replacing Phe-43 with tryptophan.
2001 Jan 30
Role of the conserved acidic residue Asp21 in the structure of phosphatidylinositol 3-kinase Src homology 3 domain: circular dichroism and nuclear magnetic resonance studies.
2001 Jan 9
Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue.
2001 Mar
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
Combined pituitary hormone deficiency due to the F135C human Pit-1 (pituitary-specific factor 1) gene mutation: functional and structural correlates.
2001 Mar
Ligand migration in human myoglobin: steric effects of isoleucine 107(G8) on O(2) and CO binding.
2001 Mar
Detection of hydroxyl radicals by D-phenylalanine hydroxylation: a specific assay for hydroxyl radical generation in biological systems.
2001 Mar 1
Activation of BMK1 via tyrosine 1062 in RET by GDNF and MEN2A mutation.
2001 Mar 2
Tight control of exogenous SERCA expression is required to obtain acceleration of calcium transients with minimal cytotoxic effects in cardiac myocytes.
2001 Mar 2
Crystallographic and solution studies of an activation loop mutant of the insulin receptor tyrosine kinase: insights into kinase mechanism.
2001 Mar 30
Patents

Sample Use Guides

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 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 Mon Mar 31 17:46:29 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:29 GMT 2025
Record UNII
47E5O17Y3R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
L-PHENYLALANINE
FCC   FHFI   USP-RS  
Preferred Name English
Phenylalanine
EP   HSDB   II   INCI   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
INCI   USAN   INN  
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 [INN]
Common Name English
PHENYLALANINE [MI]
Common 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
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JECFA EVALUATION L-PHENYLALANINE
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DSLD 1580 (Number of products:829)
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NCI_THESAURUS C68442
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Code System Code Type Description
HSDB
1825
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PRIMARY
DRUG CENTRAL
2144
Created by admin on Mon Mar 31 17:46:29 GMT 2025 , Edited by admin on Mon Mar 31 17:46:29 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-568-1
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PRIMARY
NCI_THESAURUS
C29601
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PRIMARY
JECFA MONOGRAPH
1418
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PRIMARY
MESH
D010649
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PRIMARY
PUBCHEM
6140
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PRIMARY
INN
6168
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PRIMARY
CHEBI
58095
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PRIMARY
SMS_ID
100000092416
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PRIMARY
FDA UNII
47E5O17Y3R
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PRIMARY
ChEMBL
CHEMBL301523
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PRIMARY
CAS
63-91-2
Created by admin on Mon Mar 31 17:46:29 GMT 2025 , Edited by admin on Mon Mar 31 17:46:29 GMT 2025
PRIMARY
CHEBI
29997
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PRIMARY
DRUG BANK
DB00120
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PRIMARY
RXCUI
8156
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PRIMARY RxNorm
EVMPD
SUB32327
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PRIMARY
EVMPD
SUB09786MIG
Created by admin on Mon Mar 31 17:46:29 GMT 2025 , Edited by admin on Mon Mar 31 17:46:29 GMT 2025
PRIMARY
NSC
79477
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PRIMARY
WIKIPEDIA
PHENYLALANINE
Created by admin on Mon Mar 31 17:46:29 GMT 2025 , Edited by admin on Mon Mar 31 17:46:29 GMT 2025
PRIMARY
RS_ITEM_NUM
1530503
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PRIMARY
CHEBI
17295
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PRIMARY
DAILYMED
47E5O17Y3R
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PRIMARY
MERCK INDEX
m8652
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PRIMARY Merck Index
CHEBI
28044
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PRIMARY
EPA CompTox
DTXSID4040763
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PRIMARY
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ENZYME->SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
INHIBITOR -> TARGET
DEGRADENT -> PARENT
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