L-Phenylalanine

Modify Date: 2024-01-02 10:10:18

L-Phenylalanine Structure
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].

 Names

Name L-phenylalanine
Synonym More Synonyms

 L-Phenylalanine Biological Activity

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
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.

 Chemical & Physical Properties

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

 Toxicological Information

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)

 Safety Information

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

 Synthetic Route

 Customs

HS Code 29224995

 Articles233

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 Synonyms

Benzenepropanethioic acid,S-phenyl ester
(S)-phenylalanine
L-Phenylalanine
EINECS 200-568-1
(2S)-2-amino-3-phenylpropanoic acid
L-PHENYLALININE
α-Amino-β-phenylpropionic acid, L-
H-Phe-OH
Alanine, 3-phenyl-
L-phenylalanine zwitterion
S-phenylalanine
(S)-(-)-Phenylalanine
Thiohydrozimtsaeurephenylester
(S)-a-Amino-b-phenylpropionic Acid
Alanine, phenyl-, L-
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
α-Aminohydrocinnamic acid, L-
(L)-Phenylalanine
Phenylalanine (VAN)
Phenylalanine, L-
Benzenepropanoic acid, α-amino-, (S)-
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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17942-32-4
L-Phenylalanine-d1
54793-54-3
L-Phenylalanine-d5
56253-90-8
L-Phenylalanine-15N
29700-34-3
DNP-L-PHENYLALANINE
1655-54-5
L-Phenylalanine-13C6
180268-82-0
L-phenylalanine βine
56755-22-7
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