L-Phenylalanine

Modify Date: 2025-08-20 19:12:32

L-Phenylalanine structure	Common Name	L-Phenylalanine
	CAS Number	63-91-2	Molecular Weight	165.189
	Density	1.2±0.1 g/cm3	Boiling Point	307.5±30.0 °C at 760 mmHg
	Molecular Formula	C₉H₁₁NO₂	Melting Point	270-275ºC (dec.)(lit.)
	MSDS	USA	Flash Point	139.8±24.6 °C

Use of L-Phenylalanine

L-Phenylalanine is an antagonist at α2δ calcium channels with a Ki of 980 nM. IC50 Value: 980 nM [1]Target: Calcium ChannelL-Phenylalanine (LPA) is an electrically neutral amino acid, one of the twenty common amino acids used to biochemically form proteins. In the brain, L-phenylalanine is a competitive antagonist at the glycine binding site of NMDA receptor and at the glutamate binding site of AMPA receptor [2, 3]. At the glycine binding site of NMDA receptor L-phenylalanine has an apparent equilibrium dissociation constant (KB) of 573 ?M estimated by Schild regression [4] which is considerably lower than brain L-phenylalanine concentration observed in untreated human phenylketonuria [5]. L-Phenylalanine also inhibits neurotransmitter release at glutamatergic synapses in hippocampus and cortex with IC50 of 980 nM, a brain concentration seen in classical phenylketonuria, whereas D-phenylalanine has a significantly smaller effect [3].

Name	L-phenylalanine
Synonym	More Synonyms

Description	L-Phenylalanine is an antagonist at α2δ calcium channels with a Ki of 980 nM. IC50 Value: 980 nM [1]Target: Calcium ChannelL-Phenylalanine (LPA) is an electrically neutral amino acid, one of the twenty common amino acids used to biochemically form proteins. In the brain, L-phenylalanine is a competitive antagonist at the glycine binding site of NMDA receptor and at the glutamate binding site of AMPA receptor [2, 3]. At the glycine binding site of NMDA receptor L-phenylalanine has an apparent equilibrium dissociation constant (KB) of 573 ?M estimated by Schild regression [4] which is considerably lower than brain L-phenylalanine concentration observed in untreated human phenylketonuria [5]. L-Phenylalanine also inhibits neurotransmitter release at glutamatergic synapses in hippocampus and cortex with IC50 of 980 nM, a brain concentration seen in classical phenylketonuria, whereas D-phenylalanine has a significantly smaller effect [3].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Research Areas >> Metabolic Disease Natural Products >> Phenylpropanoids
References	[1]. Mortell, K.H., et al., Structure-activity relationships of alpha-amino acid ligands for the alpha2delta subunit of voltage-gated calcium channels. Bioorg Med Chem Lett, 2006. 16(5): p. 1138-41. [2]. Glushakov, A.V., et al., Specific inhibition of N-methyl-D-aspartate receptor function in rat hippocampal neurons by L-phenylalanine at concentrations observed during phenylketonuria. Mol Psychiatry, 2002. 7(4): p. 359-67. [3]. Glushakov, A.V., et al., L-phenylalanine selectively depresses currents at glutamatergic excitatory synapses. J Neurosci Res, 2003. 72(1): p. 116-24. [4]. Glushakov, A.V., et al., Long-term changes in glutamatergic synaptic transmission in phenylketonuria. Brain, 2005. 128(Pt 2): p. 300-7. [5]. Moller, H.E., et al., Brain imaging and proton magnetic resonance spectroscopy in patients with phenylketonuria. Pediatrics, 2003. 112(6 Pt 2): p. 1580-3.

Description

Related Catalog

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Metabolic Disease

Natural Products >> Phenylpropanoids

References

[1]. Mortell, K.H., et al., Structure-activity relationships of alpha-amino acid ligands for the alpha2delta subunit of voltage-gated calcium channels. Bioorg Med Chem Lett, 2006. 16(5): p. 1138-41.

[2]. Glushakov, A.V., et al., Specific inhibition of N-methyl-D-aspartate receptor function in rat hippocampal neurons by L-phenylalanine at concentrations observed during phenylketonuria. Mol Psychiatry, 2002. 7(4): p. 359-67.

[3]. Glushakov, A.V., et al., L-phenylalanine selectively depresses currents at glutamatergic excitatory synapses. J Neurosci Res, 2003. 72(1): p. 116-24.

[4]. Glushakov, A.V., et al., Long-term changes in glutamatergic synaptic transmission in phenylketonuria. Brain, 2005. 128(Pt 2): p. 300-7.

[5]. Moller, H.E., et al., Brain imaging and proton magnetic resonance spectroscopy in patients with phenylketonuria. Pediatrics, 2003. 112(6 Pt 2): p. 1580-3.

Density	1.2±0.1 g/cm3
Boiling Point	307.5±30.0 °C at 760 mmHg
Melting Point	270-275ºC (dec.)(lit.)
Molecular Formula	C₉H₁₁NO₂
Molecular Weight	165.189
Flash Point	139.8±24.6 °C
Exact Mass	165.078979
PSA	63.32000
LogP	1.11
Vapour Pressure	0.0±0.7 mmHg at 25°C
Index of Refraction	1.576
InChIKey	COLNVLDHVKWLRT-QMMMGPOBSA-N
SMILES	NC(Cc1ccccc1)C(=O)O

L-Phenylalanine MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AY7535000

CHEMICAL NAME :: Alanine, phenyl-, L-

CAS REGISTRY NUMBER :: 63-91-2

LAST UPDATED :: 199706

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C9-H11-N-O2

MOLECULAR WEIGHT :: 165.21

WISWESSER LINE NOTATION :: QVYZ1R -L

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5287 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1322 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 276 gm/kg/13W-C

TOXIC EFFECTS :: Behavioral - alteration of operant conditioning Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 220 gm/kg

SEX/DURATION :: male 2 week(s) pre-mating female 2 week(s) pre-mating - 3 week(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 160 gm/kg

SEX/DURATION :: male 2 week(s) pre-mating female 2 week(s) pre-mating - 8 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 192 gm/kg

SEX/DURATION :: male 2 week(s) pre-mating female 2 week(s) pre-mating - 15 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 21750 mg/kg

SEX/DURATION :: female 15-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 30 gm/kg

SEX/DURATION :: female 10-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 7930 mg/kg

SEX/DURATION :: female 8-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1980 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2640 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 6048 mg/kg

SEX/DURATION :: female 8-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Effects on Newborn - biochemical and metabolic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 30 mg/kg

SEX/DURATION :: female 3 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 33600 mg/kg

SEX/DURATION :: female 1-24 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 10 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 280,279,1992 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5534 No. of Facilities: 792 (estimated) No. of Industries: 4 No. of Occupations: 14 No. of Employees: 19901 (estimated) No. of Female Employees: 14903 (estimated)

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	C: Corrosive;
Risk Phrases	R36/37/38
Safety Phrases	22-24/25-37/39-45-36/37/39-27-26
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	AY7535000
HS Code	29224995

Precursor 6
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DownStream 10
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HS Code	29224995

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Name: pKa (acid-base dissociation constant) as determined by Avdeef ref: DOI: 10.1002/04714...
Source: ChEMBL
Target: N/A
External Id: CHEMBL2449007

Name: Cis-inhibition of human LAT1 expressed in TREx HEK293 cells at 200 uM assessed as inh...
Source: ChEMBL
Target: Large neutral amino acids transporter small subunit 1
External Id: CHEMBL4386800

Name: Activity of human recombinant CA2 cytosolic isoform after 15 mins by phenol red stain...
Source: ChEMBL
Target: Carbonic anhydrase 2
External Id: CHEMBL2156561

Name: Activity of Sulfurihydrogenibium yellowstonense YO3AOP1 recombinant CA expressed in E...
Source: ChEMBL
Target: N/A
External Id: CHEMBL2156562

Name: Activity of Sulfurihydrogenibium yellowstonense YO3AOP1 recombinant CA expressed in E...
Source: ChEMBL
Target: N/A
External Id: CHEMBL2156559

Name: Activity of human recombinant CA1 cytosolic isoform after 15 mins by phenol red stain...
Source: ChEMBL
Target: Carbonic anhydrase 1
External Id: CHEMBL2156560

Name: Activation of recombinant human carbonic anhydrase 2 at 10 uM incubated for 15 mins p...
Source: ChEMBL
Target: Carbonic anhydrase 2
External Id: CHEMBL3870984

Name: Activation of recombinant Methanosarcina thermophila gamma carbonic anhydrase at 10 u...
Source: ChEMBL
Target: Carbonic anhydrase
External Id: CHEMBL3870985

Name: Activation of Burkholderia pseudomallei gamma carbonic anhydrase at 10 uM incubated f...
Source: ChEMBL
Target: N/A
External Id: CHEMBL3870986

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Source: ChEMBL
Target: N/A
External Id: CHEMBL3772432

Total 249, Current Page 1 of 25

Benzenepropanethioic acid,S-phenyl ester

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EINECS 200-568-1

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L-PHENYLALININE

H-Phe-OH

L-phenylalanine zwitterion

S-phenylalanine

(S)-(-)-Phenylalanine

Thiohydrozimtsaeurephenylester

(S)-a-Amino-b-phenylpropionic Acid

L-2-Amino-3-phenylpropionic acid

(S)-2-Amino-3-phenylpropionic acid

(S)-2-Amino-3-phenylpropanoic acid

C6H5CH2CH(NH2)COOH

(S)-a-Aminohydrocinnamic Acid

Phenylalanine

(L)-Phenylalanine

Phenylalanine (VAN)

l-Phe

PhE

phenyl 4-phenylthiobutanoate

S-Phenyl-3-phenylpropanthioat

β-phenyl-L-alanine

(-)-Phenylalanine

(S)-α-Aminobenzenepropanoic acid

MFCD00064227

3-Phenylpropionyl-phenyl-thioether

α-Amino-β-phenylpropionic acid

3-Phenylthiopropionic acid,S-phenyl ester

(S)-A-Aminobenzenepropanoic Acid

Acetylcysteine Impurity 3

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L-Phenylalanine

Use of L-Phenylalanine

Names

L-Phenylalanine Biological Activity

Chemical & Physical Properties

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

Synthetic Route

Precursor & DownStream

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Articles233

L-PhenylalanineBioassay

Synonyms

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