PHENYLALANINE

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Substrate 661
Glutamate NMDA receptor 46	Modulator 828		1.71 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Burns 17	Primary	Approved 8,429	FREAMINE III 10%
Pain 614	Primary	Not Provided 504	Unknown
Depression 235	Primary	Not Provided 504	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1389 μM	20 mg/kg single, intravenous		PHENYLALANINE plasma	Rattus norvegicus

AUC

Value	Dose	Co-administered	Analyte	Population
35.7 μM × h	20 mg/kg single, intravenous		PHENYLALANINE plasma	Rattus norvegicus

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 min	20 mg/kg single, intravenous		PHENYLALANINE plasma	Rattus norvegicus

Doses

Doses

Show entries

Dose	Population	Adverse events
1.5 g single, oral	healthy, 36 years
8.2 g single, intravenous Highest studied dose	healthy, adult

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Sourcing

Sourcing

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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
Aaron Chemicals	AR001MWG	http://www.aaronchem.com/150-30-1
abcr GmbH	AB118462	http://www.abcr.com/shop/en/AB118462
abcr GmbH	AB354874	http://www.abcr.com/shop/en/AB354874

Showing 1 to 5 of 92 entries

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PubMed

Show entries

Title	Date	PubMed
Primary structure, functional characteristics and tissue expression pattern of human ATA2, a subtype of amino acid transport system A.	2000 Jul 31	10930503
Association between minihaplotypes and mutations at the PAH locus in Polish hyperphenylalaninemic patients.	2001	11096279
Self-association of the H3 region of syntaxin 1A. Implications for intermediates in SNARE complex assembly.	2001 Apr 20	11118447
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
Development of procedures for determining the amino acid requirements of chickens by the indicator amino acid oxidation method.	2001 Feb	11233006

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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)