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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11NO2.ClH
Molecular Weight 201.65
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLALANINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=ZAIZDXVMSSDZFA-QRPNPIFTSA-N
InChI=1S/C9H11NO2.ClH/c10-8(9(11)12)6-7-4-2-1-3-5-7;/h1-5,8H,6,10H2,(H,11,12);1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

5.4345601E10
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 (total)
Highest studied dose
Dose: 8.2 g
Route: intravenous
Route: single
Dose: 8.2 g
Sources:
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Signal-binding specificity of the mu4 subunit of the adaptor protein complex AP-4.
2001 Apr 20
Mutation analysis of phenylketonuria in Yamagata prefecture, Japan.
2001 Feb
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
In vivo protein synthetic rates of atrial, ventricular, and pulmonary tissue proteins in aortic constriction, goldblatt, and bromoethylamine models of hypertension.
2001 Feb
Implicit solvent model studies of the interactions of the influenza hemagglutinin fusion peptide with lipid bilayers.
2001 Feb
American Academy of Pediatrics: Maternal phenylketonuria.
2001 Feb
Effects of the potent analgesic enkephalin-catabolizing enzyme inhibitors RB101 and kelatorphan on respiration.
2001 Feb 1
FDA approves nateglinide for treatment of type 2 diabetes.
2001 Feb 15
Cloning of dopamine, norepinephrine and serotonin transporters from monkey brain: relevance to cocaine sensitivity.
2001 Feb 19
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
Beta-adrenoceptor stimulation attenuates the hypertrophic effect of alpha-adrenoceptor stimulation in adult rat ventricular cardiomyocytes.
2001 Jan
Net amino acid flux across the fetal liver and placenta during spontaneous ovine parturition.
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
An in vivo study of ovine placental transport of essential amino acids.
2001 Jan
Serine 187 is a crucial residue for allosteric regulation of Corynebacterium glutamicum 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase.
2001 Jan 1
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
Analysis of the subsite specificity of rat insulysin using fluorogenic peptide substrates.
2001 Jan 12
A single arginyl residue in plastocyanin and in cytochrome c(6) from the cyanobacterium Anabaena sp. PCC 7119 is required for efficient reduction of photosystem I.
2001 Jan 5
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
Outer sphere mutations perturb metal reactivity in manganese superoxide dismutase.
2001 Jan 9
Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue.
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
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
Selected Contribution: IGF-I antibody prevents increases in protein synthesis in epitrochlearis muscles from refed, diabetic rats.
2001 Mar
Activation of BMK1 via tyrosine 1062 in RET by GDNF and MEN2A mutation.
2001 Mar 2
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 Fri Dec 15 18:09:36 UTC 2023
Edited
by admin
on Fri Dec 15 18:09:36 UTC 2023
Record UNII
L6O14A5L6Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLALANINE HYDROCHLORIDE
Systematic Name English
L-PHENYLALANINE, HYDROCHLORIDE (1:1)
Systematic Name English
.BETA.-PHENYL-L-ALANINE HYDROCHLORIDE
Systematic Name English
L-PHENYLALANINE, HYDROCHLORIDE
Systematic Name English
ALANINE, PHENYL-, HYDROCHLORIDE, L-
Systematic Name English
PHENYLALANINE HYDROCHLORIDE, L-
Systematic Name English
L-PHENYLALANINE HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
FDA UNII
L6O14A5L6Q
Created by admin on Fri Dec 15 18:09:36 UTC 2023 , Edited by admin on Fri Dec 15 18:09:36 UTC 2023
PRIMARY
ECHA (EC/EINECS)
241-554-5
Created by admin on Fri Dec 15 18:09:36 UTC 2023 , Edited by admin on Fri Dec 15 18:09:36 UTC 2023
PRIMARY
DRUG BANK
DBSALT001774
Created by admin on Fri Dec 15 18:09:36 UTC 2023 , Edited by admin on Fri Dec 15 18:09:36 UTC 2023
PRIMARY
CAS
17585-69-2
Created by admin on Fri Dec 15 18:09:36 UTC 2023 , Edited by admin on Fri Dec 15 18:09:36 UTC 2023
PRIMARY
PUBCHEM
12000150
Created by admin on Fri Dec 15 18:09:36 UTC 2023 , Edited by admin on Fri Dec 15 18:09:36 UTC 2023
PRIMARY
Related Record Type Details
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